Solubility of Etoricoxib in Aqueous Solutions of Glycerin, Methanol

Article pubs.acs.org/jced

Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Solubility of Etoricoxib in Aqueous Solutions of Glycerin, Methanol, Polyethylene Glycols 200, 400, 600, and Propylene Glycol at 298.2 K Pavan B. Rathi,*,†,‡ Mayura Kale,†† Jafar Soleymani,⊥ and Abolghasem Jouyban◊,# †

Shri Bhagwan College of Pharmacy, N-6, CIDCO, Aurangabad, Maharashtra 431001, India Y B Chavan College of Pharmacy, Rauza Bagh, Aurangabad, Maharashtra 431001, India †† Government College of Pharmacy, Osmanpura, Aurangabad, Maharashta 431001, India ⊥ Liver and Gastrointestinal Diseases Research Center, Tabriz University of Medical Sciences, Tabriz 51664, Iran ◊ Pharmaceutical Analysis Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz 51664, Iran # Kimia Idea Pardaz Azarbayjan (KIPA) Science Based Company, Tabriz University of Medical Sciences, Tabriz 51664, Iran ‡

S Supporting Information *

ABSTRACT: Experimental molar solubility of etoricoxib (ETR) in monosolvents such as glycerin, methanol (MeOH), polyethylene glycol 200 (PEG 200), polyethylene glycol 400 (PEG 400), polyethylene glycol 600 (PEG 600), propylene glycol (PG), and their aqueous binary solvent systems in various mass fraction compositions along with the solute-free and saturated solution densities were measured at 298.2 K. The resulting mole fraction solubility and density data were further correlated and predicted with the Jouyban−Acree model. Overall mean percentage deviations (OMPDs) between experimental and calculated mole fraction solubilities were 3.5%. The solute-free density of the monosolvents and their aqueous binary solvent systems were employed to train the model and then the densities of the saturated solutions were predicted. Moreover, OMPDs for back calculated solute-free densities and predicted saturated solution densities were 0.07% and 0.40%, respectively. Thus, the Jouyban−Acree model have potential use in preformulation and formulation studies during which solubility and density calculations are important physicochemical properties for design and development of new drug products in pharmaceutical industries. The simulated data could also be employed in crystallization and other related process design in the pharmaceutical/chemical industry.

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daily dose is relatively low.5 It has low solubility and high permeability and could be classified as a class II drug according to the biopharmaceutics classification system (BCS),6 since it does not meet the current FDA criteria for high solubility to be classified as class I drug.7,8 According to the literature, ETR is relatively insoluble in water since it could not effectively break the lattice structure of water and shows pH-dependent solubility, which creates hindrances in its in vivo bioavailability and development of parenteral formulations, ultimately restricting its therapeutic use.9 ETR is an official drug in the Indian Pharmacopoiea since 2014,10 unfortunately the information about its physicochemical properties such as solubility is not yet complete. Solubility is defined in quantitative terms as the maximum amount of a solute dissolved in a given volume of the solution phase when equilibrium exists between the residual solid phase and the solution phase at definite temperature.11 Aqueous

INTRODUCTION The IUPAC name of etoricoxib (ETR) had been proposed as 5-chloro-6′-methyl-3-[4-(methylsulfonyl)phenyl]-2,3′-bipyridine and its molecular structure is presented in Figure 1. It is an

Figure 1. Chemical structure of etoricoxib.

off-white crystalline powder and highly selective second generation cyclooxygenage-2 (COX-II) inhibitor administered as an analgesic and a nonsteroidal anti-inflammatory drug (NSAID).1 It is highly recommended in the treatment of rheumatoid arthritis, osteoarthritis, postoperative dental pain, chronic low back pain, and acute gout.2−4 It is commercially available in both tablet as well as injection dosage forms and its © XXXX American Chemical Society

Received: August 3, 2017 Accepted: December 21, 2017

A

DOI: 10.1021/acs.jced.7b00709 J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data

Article

potential use of PEG 400 in enhancing the solubility of various poorly water-soluble drugs such as meloxicam,51 acetaminophen,52 indomethacin,53 tadalafil,54 isatin,55 and silymarin.56 Similar studies also showed the solubility behavior of hydrophobic drugs such as acetaminophen, ibuprofen, pioglitazone hydrochloride, lamotrigine, clonazepam, and diazepam in aqueous and nonaqueous PEG 600 systems.57−60 PG is a colorless, odorless, viscous organic liquid and it has been used almost exclusively in the production of water insoluble drugs.19 Moreover, it can be used as solvent and diluent in pharmaceutical preparations. Because of its high stability and low toxicity,61 it is used in many commercially available pharmaceutical parenteral formulations such as diazepam, fenoldopam mesylate, melphalan HCl, oxytetracycline, paricalcitol, pentobarbital Na, phenytoin Na, chlordiazepoxide HCl, lorazepam, and phenobarbital.62 PG is also used in many oral formulations of drugs including amprenavir, clofazimine, cyclosporine A, digoxin, lopinavir, ritonavir, sirolimus, loratadine, and itraconazole.63 In a previous work,64 the solubility of ETR in aqueous binary mixtures of 1,4-butanediol, 1,4-dioxane, N,N-dimethylacetamide, N,N-dimethylformamide, dimethyl sulfoxide, and ethanol at 298.2 K is reported along with their mathematical representation using common cosolvency models. To continue our systematic investigations on the solubility of low soluble drugs, in this present investigation, the solubility of ETR was measured in water, glycerin, MeOH, PEG 200, PEG 400, PEG 600, PG and their aqueous binary solvent systems in various compositions at 298.2 K. Moreover, to the best of author’s knowledge, no reports were found about solubility of ETR in these organic monosolvents and their aqueous binary solvent systems at 298.2 K till date, although a recent study regarding some parameters derived from the solubility of ETR in several binary aqueous cosolvent mixtures at 298.2 K taken from earlier ́ paper64 has been reported by Martinez et al.65 The authors reported the preferential solvation parameters and other thermodynamic properties of ETR in several aqueous cosolvent mixtures from equilibrium solubilities and by using inverse Kirkwood−Buff integral method. Because of this high practical importance, it was our intention to measure and calculate the solubilities of ETR by the Jouyban−Acree model in several aqueous binary solvent systems in different compositions conformed by glycerin, MeOH, PEG 200, PEG 400, PEG 600, and PG at 298.2 K, extending in this way the available database of solubilities. This investigation further aims with a prediction of saturated solution densities in selected aqueous binary solvent systems at 298.2 K. A model could be useful if equilibrium solubility estimation within 30% in uncertainty are allowed.66 These findings were also supported for the solubility of drugs in a given cosolvent + water mixtures after training the model using a minimum number of experimental data points. These calculations further could be used in predicting the solubility at unmeasured solvent compositions and also in screening the experimentally determined solubilities to detect possible outliers for redetermination.

solubility is of utmost importance at early stages of design and development of new drug products in pharmaceutical industries. Almost 40% of the drug candidates fail to proceed beyond the initial trial stages and never reach the marketplace because of low aqueous solubility.12,13 Various techniques are used to alter the aqueous solubility of drugs such as complexation,14 pH adjustment,15,16 crystal engineering,17 salt formation,18 liquisolid compacts,19 fast releasing microparticles,20 compressing with buffers,21 solid dispersion,22,23 oil formulations,24 use of surfactant,25−27 use of prodrugs,28 and cosolvency.29−31 Addition of a cosolvent within a safest and permissible limit is the most effective method for increasing the solubility of poorly water-soluble drug candidates. The solubility behavior of drugs in aqueous cosolvent mixtures or binary solvent mixtures are important in purification methods, preformulation studies, and pharmaceutical dosage forms design, among other applications and also provides useful data for better understanding of the solubility phenomenon in these media.32−35 The method often used to optimize the solvent composition of solvent mixtures for dissolving a desired amount of a drug in a given volume of the solution is the trialand-error approach, which is time-consuming and expensive. About cosolvency, efforts have been devoted to represent several mathematical models not only for estimation, correlation, and prediction of drug solubility but also for other physicochemical properties in water-cosolvent mixtures.36−38 Of the numerous models developed in recent years, the log− linear model of Yalkowsky is the simplest and the Jouyban− Acree model is perhaps one of the most accurate, simple, and versatile models among similar algorithms, that provides very accurate mathematical descriptions for how the solute solubility varies with both temperature and solvent composition.39,40 Most commonly used and selected cosolvents in design and development of liquid oral and parenteral dosage forms are glycerin, polyethylene glycols (PEGs), and propylene glycol (PG), except methanol (MeOH).41 Several examples of pharmaceutical formulations using these cosolvents have been presented by Rubino.32 All these cosolvents are mainly used for solubilization and stabilization of a number of poorly soluble and/or degradable drugs in aqueous solutions. Although MeOH is not acceptable pharmaceutically because of its toxicity, it can also be used in other applications in chemical/ pharmaceutical industries, and as per our literature findings, still it has been extensively used in recrystallization of drugs and was also employed by several authors as a model cosolvent for prediction of drug solubility.33,42 Several temperature-dependent studies proved the potential use of glycerin for solubilization of furosemide,43 menadione sodium bisulfite,44 2-methyl-1,4-naphthoquinone,45 p-aminophenol,46 and paracetamol47 in binary solvent systems in all possible proportions. The polymerized derivatives of ethylene glycols (EGs), mainly, lower molecular weight liquid PEGs 200, 400, and 600 are similar in structure and widely accepted industrial solvents for preclinical and clinical studies48 because of their favorable properties such as nonirritating, low volatility, low toxicity, low melting point, high chemical stability, and complete miscibility with water. These cosolvents find a variety of applications in pharmaceutical, chemical, cosmetic, and food industries.49 Apart from the solubilization power of PEG 200, specifically it also possesses stabilization ability on the enzymes and facilitates the biotransformation of low aqueous soluble substrates in aqueous solutions.50 Several studies proved the

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EXPERIMENTAL SECTION Materials. A white crystalline powder of ETR was kindly supplied by the Dr. Reddy’s Laboratories Ltd., Hyderabad. Glycerin (IUPAC name, 1,2,3-propanetriol), methyl alcohol (IUPAC name, methanol), polyethylene glycol 200 (IUPAC name, poly(ethylene oxide)-200), polyethylene glycol 400 (IUPAC name, poly(ethylene oxide)-400), polyethylene glycol B



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Table 1. Sample Table for Materials Used in the Experiment materials

CASRN

molecular formula

molar mass g·mol−1

dielectric constant (ε)

mass fraction purity

analysis method

≥0.990

HPLCa

source

ETR

202409-33-4

C18H15N2O2SCl

358.84

glycerin methanol polyethylene glycol200 polyethylene glycol400 polyethylene glycol600 propylene glycol water

56-81-5 67-56-1 25322-68-3

C3H8O3 CH4O H(OCH2CH2)nOH

92.09 32.04 190−210

42.5 32.7 ∼21.1

≥0.995 ≥0.999 ≥0.999

GCb GCb GCb

Dr. Reddy’s Laboratory Ltd. Merck Merck Merck

25322-68-3

H(OCH2CH2)nOH

380−420

∼13.7

≥0.999

GCb

Merck

25322-68-3

H(OCH2CH2)nOH

570−630

∼11.6

≥0.999

GCb

Merck

57-55-6 7732-18-5

C3H8O2 H2O

76.09 18.02

32.0 78.5

≥0.995 1.000

GCb

Merck Obtained by distillation

a

High performance liquid chromatography (HPLC). bGas chromatography (GC).

approximate quantity of pure ETR powder was added to 10 g of the monosolvents or each binary solvent systems in stoppered dark glass flasks. The flasks with the solute-binary solvent systems were placed on a shaker equipped with thermostatically controlled water baths maintained at 298.2 (±0.05) K for at least 72 h to reach equilibrium. Previous studies showed that this time period was sufficient for nonviscous solvent systems (MeOH + water and PG + water) to ensure saturation equilibrium of solute at the same temperature. Because of high viscosity of PEGs and glycerin, saturation equilibrium was attained after 96 h.47,59 Further this equilibrium time was validated by quantifying the solute concentrations up to obtained constant values.69 Once at equilibrium, saturated solutions of the drug were centrifuged at 13000 rpm for 15 min and then the obtained supernatant solutions were filtered at isothermal conditions through membrane filters (0.22 μm, Millipore Corp., Billerica, MA, USA) to ensure that they were free of undissolved particles before sampling for respective composition analyses. Preliminary studies showed that the drug did not significantly adsorb onto the membrane filters.70 ETR concentrations were measured in moles per liter by a double beam spectrophotometer (Shimadzu-1700, Kyoto, Japan) at 247 nm after dilutions with definite proportion of MeOH + water system. A standard calibration curve was constructed by plotting ETR concentrations versus absorbance and the proposed spectrophotometric method was observed linear in the concentration range of 5 to 35 μg·mL−1 with correlation coefficient of 0.9999 (Figure S1 of Supporting Information). The densities of the monosolvents, solute-free binary solvent systems and the filtrates of saturated solutions were measured using 10 mL density bottle (previously calibrated with double distilled, deionized water) at 298.2 (±0.05) K using an analytical balance (Shimadzu AY-220, Japan) with uncertainty of ±0.0001 g. Once the densities are known, solubilities can be expressed either in mole fraction or molarity scale. Note that all the experimental solubilities and density results are the averages of measurements conducted in at least triplicate. The relative standard deviations (%RSDs) for the solubility and density measurements were 0.9% and 0.03%, respectively, and all the significant figures were defined according to the literature.71 Calculation Procedures. Mean percentage deviations (MPD) between the predicted and observed (molar/mole fraction solubilities/densities) values were estimated to assess the accuracy of the proposed model, using72,73

600 (IUPAC name, poly(ethylene oxide)-600) and propylene glycol (IUPAC name, 1,2-propanediol) were purchased from Merck, Mumbai. All the materials were of analytical reagent grade (AR grade) and used as received from the companies without further purifications. Double distilled, deionized water was used throughout the experimentation for the preparation of binary solvent mixtures and their further dilutions. The general information about drug and solvents used in the experiment is presented in Table 1. Solvent Mixtures Preparation. All cosolvent (1) and water (2) binary solvent systems were prepared by mass, using an Schimadzu electronic analytical balance with sensitivity ±0.1 mg, in quantities of 30 g. The mass fractions of cosolvent of the nine binary systems prepared varied by 0.10 from 0.10 to 0.90 to cover all the rank of compositions. X-ray Powder Diffraction. The X-ray powder diffraction (XRPD) was performed to identify the crystalline form of ETR used in this experiment. The XRPD patterns were obtained by using a PANalytical X’Pert PRO diffractometer with Cu Kα1 radiation line (λ = 0.15405 nm). It was operated in continuous mode in the 2-theta range from 5° to 50° and angle variation of 0.02° with detector data acquisition time of 25 s, electric current of 40 mA with tube voltage of 45 kV. Figure 2 reveals the XRPD patterns of raw ETR compared with solid phases in equilibrium with saturated solutions. Apparatus and Procedures. Various experimental methods could be used for determination of the drug’s solubility,67 and in continuation with our previous studies, the equilibrium saturation solubility of ETR in various monosolvents and their aqueous binary solvent systems were measured using a classical shake-flask method of Higuchi and Connors.68 Briefly, an

Figure 2. X-ray powder diffraction patterns of etoricoxib: (A) raw material; (B) solid phases in equilibrium with saturated solutions. C



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Table 2. Experimental Molar Solubilities, CSat m,T, of Etoricoxib in Aqueous Solutions of Glycerin, MeOH, PEG 200, PEG 400, PEG 600, and PG at 298.2 K and at Atmospheric Pressure (0.1 MPa), Their Relative Standard Deviations (RSD), Mole Fraction a Solubilities (XSat m,T), Densities of the Saturated Solutions, and Mass (w1) Fractions of Solvent (1) Indicated by (1) w1

103 (CSat m,T)

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.873 0.877 0.925 1.99 4.25 12.1 44.1 139 409 789 685

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.873 0.905 1.34 2.70 6.26 15.7 52.1 177 429 790 686

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.873 1.66 3.13 6.07 13.9 34.5 93.7 251 597 880 694

0.00 0.10 0.20 0.30

0.873 1.82 3.19 6.08

MPD =

100 N

100RSD

103 (XSat m,T)

density/g·cm−3

Glycerin (1) + Water (2) 0.66 0.0158 1.30 0.0166 1.10 0.0185 1.60 0.0425 0.40 0.0985 1.40 0.3101 1.60 1.279 1.90 4.786 2.60 18.18 1.40 48.46 1.70 56.56 MeOH (1) + Water (2) 0.66 0.0158 1.10 0.0174 1.40 0.0275 1.00 0.0593 1.10 0.1472 0.73 0.3993 0.45 1.450 0.75 5.617 1.70 16.73 1.50 41.30 1.70 37.86 PEG 200 (1) + Water (2) 0.66 0.0158 0.54 0.0326 0.70 0.0671 0.92 0.1444 0.91 0.3723 0.88 1.066 0.75 3.461 1.20 11.98 0.49 41.63 0.89 95.80 0.38 135.0 PEG 400 (1) + Water (2) 0.66 0.0158 0.77 0.0359 0.70 0.0692 0.79 0.1471

w1

0.9948 1.0350 1.0740 1.1120 1.1470 1.1820 1.2140 1.2370 1.2620 1.2940 1.2980

0.0004 0.0003 0.0004 0.0011 0.0026 0.0019 0.0176 0.0686 0.0110 0.0398 0.0336

0.40 0.50 0.60 0.70 0.80 0.90 1.00

14.9 35.7 97.9 253 637 931 696

0.9948 0.9785 0.9625 0.9475 0.9312 0.9140 0.8955 0.8760 0.8537 0.8291 0.8050

0.0004 0.0007 0.0012 0.0019 0.0151 0.0099 0.0234 0.0916 0.2002 0.1480 0.1219

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.873 2.00 3.65 6.99 16.0 42.1 107 319 637 966 790

0.9948 1.0110 1.0280 1.0440 1.0630 1.0800 1.1050 1.1170 1.1240 1.1420 1.1380

0.0004 0.0007 0.0003 0.0009 0.0037 0.0027 0.0097 0.0562 0.0769 0.0521 0.0523

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.873 1.39 2.26 4.27 9.37 22.6 70.1 226 526 844 688

0.9948 1.0116 1.0293 1.0463

0.0004 0.0002 0.0002 0.0016

⎡ Calculated − Observed ⎤ ⎥⎦ Observed

∑ ⎢⎣

103 (CSat m,T)

RSD

100RSD

103 (XSat m,T)

density/g·cm−3

PEG 400 (1) + Water (2) 0.76 0.4091 0.67 1.146 0.45 3.821 1.10 13.14 1.00 50.76 0.74 128.2 0.87 237.9 PEG 600 (1) + Water (2) 0.66 0.0158 0.77 0.0393 0.58 0.0790 0.99 0.1687 0.25 0.4401 0.18 1.356 0.12 4.228 0.96 17.35 0.74 53.18 0.40 145.1 0.71 354.0 PG (1) + Water (2) 0.66 0.0158 0.95 0.0270 0.74 0.0474 0.53 0.0976 0.77 0.2370 0.94 0.6388 0.84 2.284 0.96 8.938 0.94 27.37 0.72 59.86 0.96 60.47

RSD

1.0675 1.0850 1.1125 1.1247 1.1377 1.1463 1.1410

0.0038 0.0024 0.0124 0.0454 0.0605 0.1038 0.0251

0.9948 1.0152 1.0346 1.0555 1.0758 1.0958 1.1215 1.1304 1.1415 1.1542 1.1485

0.0004 0.0002 0.0003 0.0004 0.0013 0.0018 0.0205 0.0789 0.0919 0.0268 0.0498

0.9948 1.0045 1.0135 1.0225 1.0285 1.0370 1.0432 1.0493 1.0543 1.0652 1.0597

0.0004 0.0003 0.0004 0.0003 0.0015 0.0057 0.0079 0.0820 0.1720 0.2578 0.0866

a

Data are the average of three determinations. RSD: relative standard deviation. The relative standard uncertainty for the solubilities ur(X) is 0.005. The relative standard uncertainty for the densities ur(ρ) is 0.0005 and the standard uncertainty for temperature u(T) is 0.05 K. The relative standard uncertainty for pressure u(p) is 0.05. The relative standard uncertainty of the mass fraction of cosolvent in the binary solvent mixtures ur(w1) is 0.0001. The unit for molar solubility is mol· L−1.

between raw material and solid phases in equilibrium with saturation solutions. The patterns also revealed that the forms of both the raw material and solid phases were stable anhydrous crystalline form I without any solvates, polymorphs or amorphous forms during the entire experiment and thus the reliability of solubility measurements could be guaranteed. Experimental Data of Solubility and Density. Experimental molar and mole fraction solubility values for ETR at definite mass fraction (w) in a number of organic monosolvents and binary solvent systems containing glycerin + water, MeOH + water, PEG 200 + water, PEG 400 + water, PEG 600 + water, and PG + water at 298.2 (±0.05) K at different compositions along with their RSDs are listed in Table 2. The reported64 aqueous solubility of ETR at 298.2 K is 8.58 × 10−4 mol·L−1 which is in an excellent agreement with the corresponding value from this work, that is, 8.73 × 10−4 mol·L−1, in which the

(1)

where N is the number of experimental data points in each set of binary solvent systems. It is obvious that lower MPD values will indicate higher prediction capability of the model. All of the computation work was performed by using various statistical softwares such as statistical package for social sciences (SPSS 11.5) and MS-Excel.

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RESULTS AND DISCUSSION X-ray Powder Diffraction Analysis. The X-ray powder diffraction (XRPD) patterns verified the identity and high crystallinity of ETR used in this study. According to Figure 2, the same major intense characteristics peaks were observed at 7.14°, 9.80°, 11.87°, 12.48°, 13.10°, 15.57°, 16.65°, 18.21° D



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the investigated strong solvents in comparison to weak solvent (water). An approximate 1107-fold increase in molar solubility is obtained upon the addition of PEG 600 (0.90 w1) to aqueous solution of ETR. This could be explained by the extremely differing solvation abilities of these two solvents for ETR. Similar behavior is also examined for the remainder of the investigated binary solvent systems. If the mole fraction scale is considered, then the solubility of ETR in the neat cosolvents decreases in the order of PEG 600 > PEG 400 > PEG 200 > PG > glycerin > MeOH and in the range of 0.354, 0.238, 0.135, 0.061, 0.057, 0.038, respectively. It is interesting to note that, the mole fraction solubility is also the highest in neat cosolvents instead of neat water for PEG 600, PEG 400, PEG 200, PG, and glycerin except MeOH. The maximum mole fraction solubility for ETR in the MeOH + water system is 0.041 observed at 0.90 w1. The average minimum mole fraction solubility reported in this investigation for water is 1.580 × 10−5. The different behaviors were obtained, specially in aqueous MeOH and glycerin binary solvent systems, may be due to the definitions of each scale being mole fraction gravimetric and totally rational; whereas, molarity is volumetric and semiempirical because it does not consider the mole proportion of solvent in the mixtures.74 Otherwise the order of the solubility values from high to low is consistent with the order of the polarity of solvents, as in the sequence of PEG 600 > PEG 400 > PEG 200 > PG > MeOH > glycerin > water. One plausible explanation for this behavior is based on the principle of “like dissolves like”. According to Akerlof,76 these findings were further confirmed with dielectric constant (good index of polarity)77,78 values reported for these monosolvents in Table 1 and thus could be considered as a significant factor which influences the solubility of ETR. In general, polarity mainly influences the strength of solute− solvent van der Waals interactions.79 However, hydrogenbonding and hydrophobic interactions between solute−solvent may also play an important role in this case. To propose possible intermolecular interactions between solute and solvents, it is remarkable to note that ETR (Figure 1) has four hydrogen-bond acceptor counts, mainly two heterocyclic nitrogen atoms (N−) and free electron pairs present in both oxygen atoms of the sulfone group (−SO2−), which could form hydrogen bonds with the hydrogen donating groups of all cosolvents and water (−OH groups). Thus, ETR could behave only as a Lewis base in solution and all these solvents as a Lewis acid, although all these cosolvents and water have both proton−acceptor or proton−donor functional groups (−OH and/or −O− groups). Furthermore, due to presence of two methyl groups and the other hydrocarbon moieties in molecular structure of ETR, it could also interact by London dispersion forces. All these cosolvents and water are polar protic solvents and completely miscible with each other at all possible compositions. These cosolvents usually work by reducing the hydrogenbond density of water, thus creating a less polar environment in the bulk, resulting in more drug molecules going into solution. In addition, these investigated cosolvent systems could be worked by reducing the suface/interfacial tension between the aqueous solution and a nonpolar, hydrophobic solute such as ETR. By this means, the self association of the water is disrupted and the ability of water molecules to squeeze out ETR from its three-dimensional structure is prevented, thereby increasing solubility.75 Moreover, hydrogen bonding between

percentage difference is about 1.7%. In this work solvent 1 (strong solvent) refers to cosolvent and solvent 2 (weak solvent) is water such as glycerin (1) + water (2), MeOH (1) + water (2) and many others. In general, mole fraction is the preferred scale for thermodynamic analysis of dissolution processes. Nevertheless, molarity values are also included because this volumetric concentration scale could be useful for duties associated with design and development of liquid dosage forms at industrial pharmaceutical level.74 As per our findings, solubility can be expressed either in terms of molarity or mole fraction. If molarity scale is considered, then the equilibrium solubility of ETR in the neat cosolvents decreases in the order PEG 600 > PEG 400 > PEG 200 > PG > MeOH > glycerin and in the range of 0.790, 0.696, 0.694, 0.688, 0.686, 0.685 mol·L−1, respectively. The average minimum equilibrium solubility (solvent 2) reported in this investigation is 0.873 × 10−3 mol·L−1. The maximum equilibrium solubility for ETR in binary aqueous systems is observed at 0.90 w1 (w1 is the mass fraction of cosolvent for all investigated binary solvent systems) in a range of 0.966, 0.931, 0.880, 0.844, 0.790, and 0.789 mol·L−1 and in the sequence PEG 600 > PEG 400 > PEG 200 > PG > MeOH > glycerin, respectively. It is clear that maximum solubility is obtained in solvent mixtures instead of monosolvents (1 and 2). In all of the preceding investigated binary solvent systems, the solubility of ETR increased with solvent 1 concentration and maximum appeared at about 90% cosolvent concentration (0.90 w1). The solubility of ETR in monosolvents such as 1,4-butanediol, 1,4dioxane, N,N-dimethylacetamide, N,N-dimethylformamide, dimethyl sulfoxide, ethanol, and their aqueous binary solvent mixtures were recently reported in our previous studies.64 Apart from these studies, at the best of our knowledge, no other reports were published about experimental solubility of ETR either in molarity or mole fraction scale in the above-mentioned binary solvent systems and therefore, no direct comparison is possible although authors have reported the ETR solubility (mg·mL−1) in pure cosolvents such as PEG 400, PG, glycerin, water, and their aqueous binary solvent mixtures, follows in the order of PEG 400 > PG > glycerin > water.75 These findings were supported by our studies for the above-mentioned binary solvent systems. Several reasons for differences in solubilities could arise due to solute and solvents purity, equilibration time, temperature, analysis method, laboratory technique, typographical error, polymorphism, and among other situations described in the literature.37 In general, the addition of a small amount of less polar solvent (solvent 1) to more polar solvent (solvent 2), usually increases the solubility of a hydrophobic drug such as ETR and decreases the solubility of hydrophilic and/or ionized drugs and thus as per our interpretations it was found that a drastic increase in solubility (the difference of the molar concentrations at saturation) is observed in 0.90 w1 of solvent 1 in the series of the mass fraction between 0.0 to 1.0 of the less polar solvent. Careful examination of reported solubility data in Table 2 revealed that if strong solvent is added to a weak solvent, equilibrium molar solubility is increased very markedly (whereas at a very low level) at mass fraction of 0.1 from 0.873 × 10−3 (water) to 0.877 × 10−3 (glycerin), 0.905 × 10−3 (MeOH), 1.39 × 10−3 (PG), 1.66 × 10−3 (PEG 200), 1.82 × 10−3 (PEG 400), 2.00 × 10−3 (PEG 600). Approximately 905folds increase in the solubility is observed in the monosolvent 1 (PEG 600, w1 = 1.00) in comparison to water. Such behavior is also prominent at the same mass fraction in the remainder of E



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solution.84 In the case of a solute dissolved in a binary solvent systems, the basic thermodynamic model from which eq 2 was derived included all six possible two-body (1−1, 2−2, 3−3, 1− 2, 1−3, 2−3) and all ten possible three-body (1−1−1, 2−2−2, 3−3−3, 1−1−2, 1−2−2, 1−1−3, 1−3−3, 2−2−3, 2−3−3, 1− 2−3) molecular interactions between similar and dissimilar mixture components. This procedure produced more accurate correlations than any other method for the solute’s solubility in aqueous binary solvent systems.85 The numerical values of n can be varied between 0 and 2 in accordance with accurate mathematical representation of the available experimental data sets. Equation 2 was used to fit the experimental (observed) solubility data of ETR in investigated binary solvent systems as shown in Table 2. The resulting model constants along with the MPD values were computed and given in Table 3. By using

water molecules is broken with the help of the hydrophobic hydrocarbon region of insoluble drugs (for example, ETR), thus reducing intermolecular interaction.80 Furthermore, the small nonpolar hydrocarbon region in the cosolvent can reduce the ability of the aqueous system to squeeze out nonpolar solutes. For example, oxygen atoms and −OH groups are present in the molecular structure of PEGs, respectively, in the molecular chain and at the ends of the chain, due to which these molecules have several hydrogen bonding sites that can enter into intra- and intermolecular hydrogen bonding giving rise to several conformations in water mixtures. Thus, the increase in solubility in PEGs suggests that the hydrophobic interactions are more prominent and significant in governing the solubility of the ETR in PEGs. The high solubility of ETR in PEG 600 is probably because of extensive hydrophobic interactions. These findings were extensively supported by a mechanism of solubilization of trimethoprim by hydrophobic interactions.81 As expected, PEG 600 being less-polar exhibited better solubilization power in comparison with rest of the monosolvents. Finally, these results indicate that the ETR preferably solubilize in nonpolar environments rather than polar environment. The measured densities of the solute saturated solutions together with their RSDs are also listed in Table 2. These data of densities are required to convert molar solubilities to mole fraction scale and any attempt to predict the density of the saturated solutions could save time and cost of experimental efforts. Values of densities for monosolvents are all in the relatively small range of 0.8050, 0.9948, 1.0597, 1.1380, 1.1410, 1.1485, and 1.2980 g·cm−3, respectively, for MeOH, water, PG, PEG 200, PEG 400, PEG 600, and glycerin. Maximum saturation solution density values were obtained at 0.90 w1 for MeOH + water, PG + water, PEG 200 + water, PEG 400 + water, PEG 600 + water, and glycerin + water mixtures in a range of 0.8291, 1.0652, 1.1420, 1.1463, 1.1542, and 1.2940 g· cm−3, respectively, and follows the same trend as monosolvents. As per our expectations, these values are higher than those of the solute-free binary solvent systems. In both cases, the densities are uniformly continuous and nonlinear functions of the mass fraction without maxima which follows predictable behavior in densities of all the binary solvent systems studied. Computations of the Jouyban−Acree Model. Solubility. The Jouyban−Acree model was used to correlate different physicochemical properties in mixed solvent systems and its basic form for representing the solubility of a solute in binary solvent systems at various temperatures is82

Table 3. Jouyban−Acree Model Constants for BackCalculation of Solubility of Etoricoxib in Binary Solvent Mixtures According to eq 2a solvent systems glycerin + water MeOH + water PEG 200 + water PEG 400 + water PEG 600 + water PG + water overall:

A0

A1

A2

MPD

SD

−1305.514

2885.225

1460.902

4.6

4.6

11

−721.268

2726.411

1533.240

5.4

4.2

11

−383.937

1485.418

1642.477

1.6

1.8

11

−637.219

1150.712

1486.194

3.0

2.4

11

−690.186

801.547

1178.451

4.2

4.1

11 66

−448.358

2175.369

2100.641

2.5 3.5

1.8 3.1

a

Notation: N, number of data points; MPD, mean percentage deviation; SD, standard deviation.

these constants, it is possible to predict the solubility of ETR at any composition ranges of solvents at various temperatures employing the experimental solubility in the monosolvents, that Sat is, the values for XSat 1,T and X2,T (the data for w1 = 0.00 and w1 = 1.00). For further assessment of the quality of the calculated solubility data upon application of the Jouyban−Acree model, these constants were used to back-calculate the data by eq 2. The agreement between back-calculated and observed data was expressed by the MPD values as defined in eq 1. As a result, the best agreement, indicated by the lowest MPD value, is observed for PEG 200 + water mixtures with 1.6% (±1.8 SD), the highest MPD value is found for MeOH + water mixtures with 5.4% (±4.2 SD). The overall MPD (OMPD) value (the mean of all values) is 3.5% (±3.1 SD). In Figure 3, the experimentally measured mole fraction solubilities were plotted vs those back-calculated by the aid of the Jouyban−Acree model. Because the solubilities vary over nearly 3 orders of magnitude, a logarithmic scale can also be chosen. A linear relation (R = 0.9987) with a slight scatter around the line with slope 1 (the best relation between predicted and experimental data) can be observed, most pronounced for the solubilities in the PEG 200 + water mixtures. However, generally only slight scatter reflects the agreement between the two data sets, which by far suffices for the purpose to forecast the solubility of ETR in the binary solvents often used in practice.

log10 X mSat, T = w1 log10 X1,SatT + w2 log10 X 2,SatT ⎡w w n ⎤ + ⎢ 1 2 ∑ Ai (w1 − w2)i ⎥ ⎢⎣ T i = 0 ⎥⎦

N 11

(2)

where XSat m,T is the mole fraction solubility of the solute in the binary solvent systems at temperature T (expressed as K), w1 and w2 are the mass fractions of the solvents 1 and 2 in the Sat absence of the solute, XSat 1,T and X2,T denote the mole fraction solubility of the solute in the monosolvents 1 and 2, respectively, and Ai are computational model constants (coefficients) computed using a no intercept least-square analysis for each binary solvent system.83 The Ai coefficients in eq 2 do have theoretical signficance in that each coefficient is a function of two-body and three-body interaction energies that describe the attactions between the various molecules in F



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constants computed by eq 4 could be used in eq 3 with acceptable accuracy. The computed Ji terms using eq 4 and MPD of the back-calculated density for solute-free mixtures are listed in Table 4. Furthermore, the model constants along with the numerical values of density of saturated solutions in the monosolvents were used to predict the density of saturated solutions in binary solvent systems and then the predicted values were compared with the corresponding experimental values. The MPD for the predicted density values are also listed in Table 4. Thus, the densities of the saturated solutions of ETR at any compositions of the binary solvent systems and temperatures could be interpolated using the reported model constants.86 The observed correlation for back-calculated solute-free density data was best for PG + water mixtures with the MPD of 0.02% and the worst for glycerin + water mixtures with the MPD of 0.24%. The predicted saturated solution density values were best for PEG 200 + water and PEG 600 + water mixtures with the MPD of 0.32% and worst for glycerin + water mixtures with the MPD of 0.70%. The overall MPD of 0.07% and 0.40% was obtained for back-calculated solute-free and predicted saturated solution density data, respectively. The calculated densities were in good correlation with measured densities in investigated binary solvent mixtures (R = 0.9914) and was shown in Figure 4.

Figure 3. Plot of calculated mole fraction solubility of etoricoxib in the investigated binary solvent mixtures against the corresponding experimental values at T = 298.2 K.

Density. The density data of the saturated solutions are required in some process designs57 and are also needed to convert the molar solubility to the mole fraction solubility or Sat vice versa. The density data of the saturated solutions ρm,T of binary solvent systems (see Table 2) were predicted using eq 3: log10 ρmSat, T = w1 log10 ρ1,Sat + w2 log10 ρ2,SatT T ⎡w w n ⎤ + ⎢ 1 2 ∑ Ji (w1 − w2)i ⎥ ⎢⎣ T i = 0 ⎥⎦

ρSat 1,T

(3)

ρSat 2,T

where and are the densities of the solute saturated solution of the monosolvents 1 and 2, respectively, at temperature T(K), and Ji are the solvent−solvent and solute−solvent interaction terms computed by regressing the solute-free density data of binary solvent systems using eq 4:84 log10 ρm , T = w1 log10 ρ1, T + w2 log10 ρ2, T ⎡w w n ⎤ + ⎢ 1 2 ∑ Ji (w1 − w2)i ⎥ ⎢⎣ T i = 0 ⎥⎦

(4) Figure 4. Calculated density (ρCalc m,T ) of saturated solutions of etoricoxib −3 at T = 298.2 K. versus experimental values (ρExp m,T) in g·cm

where ρ1,T and ρ2,T are the solute-free densities of the monosolvents 1 and 2, respectively, at temperature T (K). Numerical values of the Jouyban−Acree model constants (Ji values) in both equations are nearly the same and the model

Table 4. Jouyban−Acree Model Constants for Back-Calculations of Solute-Free Density Data (eq 4) and Prediction of Density of Saturated Solutions of Etoricoxib in Binary Solvent Mixtures (eq 3)a MPD

a

solvent systems

N

J0

J1

glycerin + water MeOH + water PEG 200 + water PEG 400 + water PEG 600 + water PG + water overall:

11 11 11 11 11 11 66

33.515 18.662 27.076 27.185 27.362 6.441

b 3.444 15.775 15.558 15.504

J2

back-calculations for solute-free data

prediction using trained model by solute-free data

0.24 0.05 0.04 0.04 0.04 0.02 0.07

0.70 0.41 0.32 0.34 0.32 0.34 0.40

−11.177 −5.355 −5.311 −5.394

Notation: MPD, mean percentage deviation; N: number of data points. bNot statistically significant (p > 0.05). G



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(2) Brooks, P. M.; Kubler, P. Etoricoxib For Arthritis and Pain Management. Ther. Clin. Risk Manage. 2006, 2, 45−57. (3) Patrignani, P.; Capone, M. L.; Tacconelli, S. Clinical Pharmacology of Etoricoxib: A Novel Selective COX2 Inhibitor. Expert Opin. Pharmacother. 2003, 4, 265−284. (4) Patel, D. M.; Patel, M. M. Optimization of Fast Dissolving Etoricoxib Tablets Prepared by Sublimation Technique. Ind. J. Pharm. Sci. 2008, 70, 71−76. (5) Cochrane, D. J.; Jarvis, B.; Keating, G. M. Drugs 2002, 62, 2637− 2651. (See also discussions 2652−2653) (6) Waiver of In vivo Bioavailability and Bioequivalence Studies for Immediate-Release Solid Oral Dosage Forms Based on a Biopharmaceutics Classification System; Food and Drug Administration: Silver Spring, MD, USA, 2002. (7) Yazdanian, M.; Briggs, K.; Jankovsky, C.; Hawi, A. The ‘‘High Solubility” Definition of the Current FDA Guidance on Biopharmaceutical Classification System May Be Too Strict for Acidic Drugs. Pharm. Res. 2004, 21, 293−299. (8) Yu, L. X.; Amidon, G. L.; Polli, J. E.; Zhao, H.; Mehta, M. U.; Conner, D. P.; Shah, V. P.; Lesko, L. J.; Chen, M. L.; Lee, V. H.; Hussain, A. S. Biopharmaceutics Classification System: The Scientific Basis for Biowaiver Extensions. Pharm. Res. 2002, 19, 921−925. (9) Okumu, A.; Dimaso, M.; Löebenberg, R. Computer Simulations using GastroPlus to Justify a Biowaiver for Etoricoxib Solid Oral Drug Products. Eur. J. Pharm. Biopharm. 2009, 72, 91−98. (10) Indian Pharmacopoeia, Ministry of Health and Family Welfare. The Indian Pharmacopoeia Commission: Ghaziabad, India, 2014. (11) Liu, R. Water-Insoluble Drug Formulation; CRC Press: Boca Raton, FL, USA, 2008. (12) Soltanpour, Sh.; Acree, W. E.; Jouyban, A. Effects of Different Concentrations of Poly (vinyl pyrrolidone) on the Solubility of Lamotrigine and Diazepam in Ethanol + Water Mixtures at 298.2 K. J. Chem. Eng. Data 2010, 55, 570−573. (13) Williams, H. D.; Trevaskis, N. L.; Charman, S. A.; Shanker, R. M.; Charman, W. N.; Pouton, C. W.; Porter, C. J. Strategies To Address Low Drug Solubility in Discovery and Development. Pharmacol. Rev. 2013, 65, 315−499. (14) Brewster, M. E.; Loftsson, T. Cyclodextrins as Pharmaceutical Solubilizers. Adv. Drug Delivery Rev. 2007, 59, 645−666. (15) Bethune, S. J.; Huang, N.; Jayasankar, A.; Rodríguez-Hornedo, N. Understanding and Predicting the Effect of Cocrystal Components and pH on Cocrystal Solubility. Cryst. Growth Des. 2009, 9, 3976− 3988. (16) Reddy, L. S.; Bethune, S. J.; Kampf, J. W.; Rodríguez-Hornedo, N. Cocrystals and Salts of Gabapentin: pH Dependent Cocrystal Stability and Solubility. Cryst. Growth Des. 2008, 9, 378−385. (17) Blagden, N.; DeMatas, M.; Gavan, P. T.; York, P. Crystal Engineering of Active Pharmaceutical Ingredients to Improve Solubility and Dissolution Rates. Adv. Drug Delivery Rev. 2007, 59, 617−630. (18) Serajuddin, A. T. M. Salt Formation to Improve Drug Solubility. Adv. Drug Delivery Rev. 2007, 59, 603−616. (19) Nokhodchi, A.; Javadzadeh, Y.; Siahi-Shadbad, M. R.; BarzegarJalali, M. The Effect of Type and Concentration of Vehicles on the Dissolution Rate of a Poorly Soluble Drug (Indomethacin) From Liquisolid Compacts. J. Pharm. Pharm. Sci. 2005, 8, 18−25. (20) Cavallari, C.; Luppi, B.; DiPietra, A. M.; Rodriguez, L.; Fini, A. Enhanced Release of Indomethacin From PVP/Stearic Acid Microcapsules Prepared Coupling Co-Freeze-Drying and Ultrasound Assisted Spray-Congealing Process. Pharm. Res. 2007, 24, 521−529. (21) Preechagoon, D.; Udomprateep, A.; Manwiwattanagul, G. Improved Dissolution Rate of Poorly Soluble Drug by Incorporation of Buffers. Drug Dev. Ind. Pharm. 2000, 26, 891−894. (22) Danjo, K.; Nakata, T.; Otsuka, A. Preparation and Dissolution of Ethenzamide Solid Dispersions using Various Sugars as Dispersion Carriers. Chem. Pharm. Bull. 1997, 45, 1840−1844. (23) Save, T.; Venkitachalam, P. Studies on Solid Dispersions of Nifedipine. Drug Dev. Ind. Pharm. 1992, 18, 1663−1679.

CONCLUSIONS Experimental molar and mole fraction solubilities of ETR and saturated solution densities are reported in monosolvents and binary solvent systems of glycerin, MeOH, PEG 200, PEG 400, PEG 600, and PG with water at 298.2 K. These data could be used not only in aqueous mixtures with permisible quantity of cosolvents in liquid drug formulations such as injectables and orals but could also be in nonaqueous mixtures such as soft gelatin capsule formulations. The Jouyban−Acree model fits well to correlate and predict the solubilities and the densities at any composition of the binary solvent systems at fixed temperature, that extend the available solubility database of pharmaceuticals in water-cosolvent mixtures which is in high demand in industry.87 These findings are also supported by the small MPD values of the back-calculated and experimental (observed) mole fraction solubility and solute-free density’s data, and the produced MPDs are very low, which is within an acceptable range. According to results predicted for solute-free densities with computed model constants, it is not necessary to measure the density of all saturated solutions and by measuring the density of the solute-free solvent systems and with trained version of the Jouyban−Acree model, the density of the saturated solutions could be predicted within an acceptable MPD. Thus the predicted densities could be used for converting the molar solubility to their corresponding mole fraction scale. The overall MPD (OMPD) values observed in all these calculations show that the Jouyban−Acree model provides more accurate predictions in reported binary solvent systems for ETR, and these estimated predictions could be recommended to the pharmaceutical industry for practical applications.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jced.7b00709. A standard calibration curve for the dependence of the UV absorbance on the etoricoxib concentration (PDF)

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Tel.:+91-9970669131. ORCID

Pavan B. Rathi: 0000-0001-6043-6605 Abolghasem Jouyban: 0000-0002-4670-2783 Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS We thank Dr. Reddy’s Laboratories Ltd., Hyderabad, for providing a gift sample of etoricoxib. We are also thankful to Marathwada Mitra Mandal’s College of Pharmacy, Thergaon, Pune, for providing the necessary facilities for carrying out this research work. We are also grateful to SAIF, Punjab, Chandigarh, for providing the neceassary facilility for XRPD study.

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REFERENCES

(1) Das, A.; Nayak, A. K.; Mohanty, B.; Panda, S. Solubility and Dissolution Enhancement of Etoricoxib by Solid Dispersion Technique Using Sugar Carriers. ISRN Pharm. 2011, 2011, 1. H



Article

(24) Hauss, D. J. Oral Lipid-Based Formulations. Adv. Drug Delivery Rev. 2007, 59, 667−676. (25) Corrigan, O. I., Healy, A. M.. Surfactants in Pharmaceutical Products and Systems. In Encyclopedia of Pharmaceutical Technology; Swarbrick, J., Ed.; Marcel Dekker, Inc.: New York, 1988. (26) Park, S. H.; Choi, H. K. The Effects of Surfactants on the Dissolution Profiles of Poorly Water-Soluble Acidic Drugs. Int. J. Pharm. 2006, 321, 35−41. (27) Ullah, I.; Baloch, M. K.; Durrani, G. F. Solubility of Nonsteroidal Anti-inflammatory Drugs (NSAID) in Aqueous Solutions of Non-ionic Surfactants. J. Solution Chem. 2011, 40, 1341−1348. (28) Stella, V. J.; Nti-Addae, K. W. Prodrug Strategies to Overcome Poor Water Solubility. Adv. Drug Delivery Rev. 2007, 59, 677−694. (29) Abbasi, M.; Vaez-Gharamaleki, J.; Fazeli-Bakhtiyari, R.; Martínez, F.; Jouyban, A. Prediction of Deferiprone Solubility in Some Non-Aqueous Binary Solvent Mixtures at Various Temperatures. J. Mol. Liq. 2015, 203, 16−19. (30) Soltanpour, Sh.; Jouyban, A. Solubility of Lamotrigine and Diazepam in Propylene Glycol + Water + Carboxymethyl Cellulose at a Temperature of 298.2 K. J. Chem. Eng. Data 2010, 55, 2890−2893. (31) Zakeri-Milani, P.; Ebrahimi, S.; Valizadeh, H. Investigation of Digoxin Solubility in Different Cosolvent Systems. Pharm. Sci. 2012, 18, 87−92. (32) Rubino, J. T.. Cosolvents and Cosolvency. In Encyclopedia of Pharmaceutical Technology; Swarbrick, J., Ed.; Marcel Dekker, Inc.: New York, 1988. (33) Yalkowsky, S. H. Solubility and Solubilization in Aqueous Media; Oxford University Press: New York, 1999. (34) Marcus, Y. Solvent Mixtures: Properties and Selective Solvation; Marcel Dekker, Inc.: New York, 2002. (35) Jouyban, A.; Fakhree, M. A. A. A New Definition of Solubilization Power of a Cosolvent. Pharmazie 2008, 63, 317−319. (36) Jouyban, A.; Khoubnasabjafari, M.; Chan, H. K.; Clark, B. J.; Acree, W. E. Solubility Prediction of Anthracene in Mixed Solvents using a Minimum Number of Experimental Data. Chem. Pharm. Bull. 2002, 50, 21−25. (37) Jouyban, A. Review of the Cosolvency Models for Predicting Solubility of Drugs in Water-Cosolvent Mixtures. J. Pharm. Pharm. Sci. 2008, 11, 32−58. (38) Jouyvan-Gharamaleki, A.; Clark, B. J.; Acree, W. E. Models to Predict Solubility in Ternary Solvents Based on Sub-binary Experimental Data. Chem. Pharm. Bull. 2000, 48, 1866−1871. (39) Khoubnasabjafari, M.; Jouyban, A.; Acree, W. E. Mathematical Representation of Solubility of Electrolytes in Binary Solvent Mixtures using Jouyban−Acree Model. Chem. Pharm. Bull. 2005, 53, 1591− 1593. (40) Jouyban, A.; Khoubnasabjafari, M.; Chan, H. K.; Acree, W. E. Mathematical Representation of Solubility of Amino Acids in Binary Aqueous-Organic Solvent Mixtures at Various Temperatures using the Jouyban−Acree Model. Pharmazie 2006, 61, 789−792. (41) United State Pharmacopoeia, 23rd revision; US Pharmacopeial Convention: Rockville, MD, 1995. (42) Cárdenas, Z. J.; Jiménez, D. M.; Rodríguez, G. A.; Delgado, D. R.; Martínez, F.; Khoubnasabjafari, M.; Jouyban, A. Solubility of Methocarbamol in Several Binary Cosolvent + Water Mixtures at 298.15 K and Correlation with the Jouyban−Acree Model. J. Mol. Liq. 2013, 188, 162−166. (43) Jouyban-Gharamaleki, A.; Dastmalchi, S.; Chan, H. K.; Hanaee, J.; Javanmard, A.; Barzegar-Jalali, M. Solubility Prediction for Furosemide in Water-Cosolvent Mixtures Using the Minimum Number of Experiments. Drug Dev. Ind. Pharm. 2001, 27, 577−583. (44) Song, C. Y.; Shen, H. Z.; Zhao, J. H.; Wang, L. C.; Wang, F. A. Solubilities of Menadione Sodium Bisulfite in Water + (Methanol, Ethanol, 1-Propanol, 2-Propanol, 1, 2-Propanediol, and Glycerin, Respectively) from (297.67 to 337.76). J. Chem. Eng. Data 2008, 53, 2288−2290. (45) Song, C. Y.; Shen, H. Z.; Wang, L. C.; Zhao, J. H.; Wang, F. A. Solubilities of 2-Methyl-1,4-Naphthoquinone in Water + (Methanol,

Ethanol, 1-Propanol, 2-Propanol, 1,2-Propanediol, and Glycerin, Respectively) from (293.15 to 337.92). J. Chem. Eng. Data 2007, 52, 2018−2019. (46) Zhao, J. H.; Wang, L. C.; Wang, F. A. Solubilities of pAminophenol in Sulfuric Acid + Water + (Methanol, Ethanol, 1Propanol, 2-Propanol, 1,2-Propanediol, and Glycerin, Respectively) from (292.35 to 348.10). J. Chem. Eng. Data 2006, 51, 376−381. (47) Jouyban, A.; Fakhree, M. A. A.; Mirzaei, S.; Ghafourian, T.; Soltanpour, Sh.; Nokhodchi, A. Solubility Prediction of Paracetamol in Water-Glycerol Mixtures at 25 and 30 °C Using the Jouyban−Acree Model. Asian J. Chem. 2009, 21, 7249−7253. (48) Myrdal, P. B.; Yalkowsky, S. H. Solubilization of Drugs: Encyclopedia of Pharmaceutical Technology; Marcel Dekker, Inc; New York, 1999. (49) Harris, J. M. Poly (ethylene glycol) Chemistry: Biotechnical and Biomedical Application; Plenum: New York, 1992. (50) Spreti, N.; Germani, R.; Incani, A.; Savelli, G. Stabilization of Chloroperoxidase by Polyethylene Glycols in Aqueous Media: Kinetic Studies and Synthetic Applications. Biocatal. Bioreact. Prog. 2004, 20, 96−101. (51) Cárdenas, Z. J.; Jiménez, D. M.; Martínez, F. Solubility and Solution Thermodynamics of Meloxicam in Polyethylene Glycol 400 + Water Mixtures. J. Mol. Liq. 2015, 211, 233−238. (52) Ahumada, E. A.; Delgado, D. R.; Martínez, F. Solution Thermodynamics of Acetaminophen in Some PEG 400 + Water Mixtures. Fluid Phase Equilib. 2012, 332, 120−127. (53) Shakeel, F.; Alanazi, F. K.; Alsarra, I. A.; Haq, N. Solubility Prediction of Indomethacin in PEG 400 + Water Mixtures at Various Temperatures. J. Mol. Liq. 2013, 188, 28−32. (54) Shakeel, F.; El-Badry, M.; Haq, N.; Alanazi, F. K.; Alsarra, I. A. Solution Thermodynamics and Solubility of Tadalafil in PEG 400 + Water Co-Solvent Mixtures at 298.15 to 333.15 K. J. Drug Delivery Sci. Technol. 2014, 24, 539−542. (55) Shakeel, F.; Haq, N.; Alanazi, F. K.; Alsarra, I. A. Thermodynamics of Solubility of Isatin in (PEG 400 + Water) Mixed Solvent Systems at T = (298.15 to 338.15). J. Chem. Thermodyn. 2015, 82, 156−160. (56) Shakeel, F.; Anwer, M. K. Dissolution Thermodynamics and Solubility of Silymarin in PEG 400 - Water Mixtures at Different Temperatures. Drug Dev. Ind. Pharm. 2015, 41, 1819−1823. (57) Soltanpour, Sh.; Jouyban, A. Solubility of Acetaminophen and Ibuprofen in Polyethylene Glycol 600, N-Methyl Pyrrolidone and Water Mixtures. J. Solution Chem. 2011, 40, 2032−2045. (58) Soltanpour, Sh.; Zohrabi, F.; Bastami, Z. Thermodynamic Solubility of Pioglitazone HCl in Polyethylene Glycols 200, 400 or 600 + water Mixtures at 303.2 and 308.2 K-Data Report and Modeling. Fluid Phase Equilib. 2014, 379, 180−184. (59) Soltanpour, Sh.; Jouyban, A. Solubility of Lamotrigine in Binary and Ternary Mixtures of PEGs 200, 400, and 600 with Ethanol, PG, and Water at 298.2K. Chem. Eng. Commun. 2013, 200, 1443−1456. (60) Soltanpour, Sh.; Bastami, Z.; Panahi-Azar, V.; Jouyban, A. Solubility of Clonazepam and Diazepam in Binary and Ternary Mixtures of Polyethylene Glycols 400 or 600, Propylene Glycol and Water at 298.2 K. Experimental Data and Modeling. J. Serb. Chem. Soc. 2014, 79, 445−456. (61) Bartsch, W. G.; Sponer, G.; Dietmann, K.; Fuchs, G. Acute Toxicity of Various Solvents in the Mouse and Rat. LD50 of Ethanol, Diethylacetamide, Dimethylformamide, Dimethylsulfoxide, Glycerine, N-Methylpyrrolidone, Polyethylene Glycol 400, 1, 2-Propanediol and Tween 20. Arzneimittel-forschung. 1975, 26, 1581−1583. (62) Yalkowsky, S. H.; Rubino, J. T. Solubilization by Cosolvents I: Organic Solutes in Propylene Glycol-Water Mixtures. J. Pharm. Sci. 1985, 74, 416−421. (63) Strickley, R. G. Solubilizing Excipients in Oral and Injectable Formulations. Pharm. Res. 2004, 21, 201−230. (64) Rathi, P. B.; Jouyban, A.; Khoubnasabjafari, M.; Kale, M. Solubility of Etoricoxib in Aqueous Solutions of 1,4-Butanediol, 1,4Dioxane, N,N-Dimethylacetamide, N,N-Dimethylformamide, Dimethyl I



Article

Sulfoxide, and Ethanol at 298.2 K. J. Chem. Eng. Data 2015, 60, 2128− 2134. (65) Martínez, F.; Jouyban, A.; Acree, W. E. Preferential Solvation of Etoricoxib in Some Aqueous Binary Cosolvent Mixtures at 298.15 K. Phys. Chem. Liq. 2016, 22, 1−13. (66) Ruidiaz, M.; Rodríguez, D.; Neita, R.; Cristancho, B.; Martínez, F. Performance of the Jouyban−Acree Model for Correlating the Solubility of Indomethacin and Ethylhexyl Triazone in Ethyl Acetate + Ethanol Mixtures. Vitae 2010, 17, 309−316. (67) Jouyban, A., Fakhree, M. A. A. Experimental and Computational Methods Pertaining to Drug Solubility. In Toxicity and Drug Testing; Acree, W.E., Jr, Ed.; InTech: New York, 2012. (68) Higuchi, T.; Connors, K. A. Phase Solubility Diagram. Adv. Anal. Chem. Instrum. 1965, 4, 117−212. (69) Yalkowsky, S. H.; Amidon, G. L.; Zografi, G.; Flynn, G. L. Solubility of Nonelectrolytes in Polar Solvents III: Alkyl p-aminobenzoates in Polar and Mixed Solvents. J. Pharm. Sci. 1975, 64, 48−52. (70) Jouyban-Gharamaleki, A.; Romero, S.; Bustamante, P.; Clark, B. J. Multiple Solubility Maxima of Oxolinic Acid in Mixed Solvents and a New Extension of Hildebrand Solubility Approach. Chem. Pharm. Bull. 2000, 48, 175−178. ́ (71) Shoemaker, D. P.; Garland, G. W. Experimentos de Fisicoquimica, Unión Tipográfica Editorial Hispano Americana; México D.F., 1968. (72) Jouyban, A.; Chew, N. Y.; Chan, H. K.; Sabour, M.; Acree, W. E. A Unified Cosolvency Model for Calculating Solute Solubility in Mixed Solvents. Chem. Pharm. Bull. 2005, 53, 634−637. (73) Jouyban, A.; Khoubnasabjafari, M.; Vaez-Gharamaleki, Z.; Fekari, Z.; Acree, W. E. Calculation of the Viscosity of Binary Liquids at Various Temperatures using Jouyban−Acree Model. Chem. Pharm. Bull. 2005, 53, 519−523. (74) Martin, A. Physical Pharmacy: Physical Chemical Principles in the Pharmaceutical Sciences; B. I. Waverly Pvt Ltd: New Delhi, 1994. (75) Nayak, A. K.; Panigrahi, P. P. Solubility Enhancement of Etoricoxib by Cosolvency Approach. ISRN Phys. Chem. 2012, 2012, 1. (76) Akerlof, G. Dielectric Constants of Some Organic SolventWater Mixtures at Various Temperatures. J. Am. Chem. Soc. 1932, 54, 4125−4139. (77) Florence, A.T.; Atwood, D. Physicochemical Principles of Pharmacy, 3rd ed.; MacMillan Press Ltd.: London, 1998. (78) Marcus, Y. The Properties of Solvents; John Wiley and Sons: Chichester, New York, USA, 1999. (79) Zhou, Z.; Qu, Y.; Wang, J.; Wang, S.; Liu, J.; Wu, M. Measurement and Correlation of Solubilities of (Z)-2-(2-Aminothiazol-4-yl)-2-Methoxyiminoacetic Acid in Different Pure Solvents and Binary Mixtures of Water + (Ethanol, Methanol, or Glycol). J. Chem. Eng. Data 2011, 56, 1622−1628. (80) Miyako, Y.; Zhao, Y.; Takeshima, K.; Kataoka, T.; Handa, T.; Pinal, R. Solubility of Hydrophobic Compounds in Water-Cosolvent Mixtures: Relation of Solubility with Water-Cosolvent Interactions. J. Pharm. Sci. 2010, 99, 293−302. (81) Yin, D. P.; Liu, M. X.; Fu, H. L.; Shu, G.; Zhou, J. Y.; Qing, X. Y.; Wu, W. B. Solubility of Trimethoprim in Selected Pure Solvents and (Water + Ethanol/2-Propanol) Mixed-Solvent Systems. J. Chem. Eng. Data 2016, 61, 404−411. (82) Jouyban, A.; Azarmir, O.; Mirzaei, S.; Hassanzadeh, D.; Ghafourian, T.; Acree, W. E.; Nokhodchi, A. Solubility Prediction of Paracetamol in Water-Ethanol-Propylene Glycol Mixtures at 25 and 30 °C Using Practical Approaches. Chem. Pharm. Bull. 2008, 56, 602− 606. (83) Jouyban-Gharamaleki, A.; Hanaee, J. A Novel Method for Improvement of Predictability of the CNIBS/RK Equation. Int. J. Pharm. 1997, 154, 245−247. (84) Acree, W. E. Mathematical Representation of Thermodynamic Properties: Part 2. Derivation of the Combined Nearly Ideal Binary Solvent (NIBS)/Redlich-Kister Mathematical Representation from a Two-Body and Three-Body Interactional Mixing Model. Thermochim. Acta 1992, 198, 71−79. (85) Jouyban-Gharamaleki, A.; Valaee, L.; Barzegar-Jalali, M.; Clark, B. J.; Acree, W. E. Comparison of Various Cosolvency Models for

Calculating Solute Solubility in Water-Cosolvent Mixtures. Int. J. Pharm. 1999, 177, 93−101. (86) Jouyban, A.; Fathi-Azarbayjani, A.; Khoubnasabjafari, M.; Acree, W. E. Mathematical Representation of the Density of Liquid Mixtures at Various Temperatures using Jouyban−Acree Model. Indian J. Chem. A 2005, 44, 1553−1560. (87) Jouyban, A. Handbook of Solubility Data for Pharmaceuticals; CRC Press: Boca Raton, FL, USA, 2010.

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Solubility of Etoricoxib in Aqueous Solutions of Glycerin, Methanol

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