Solubility of Etoricoxib in Aqueous Solutions of 1, 4-Butanediol, 1, 4

Jun 22, 2015 - (3, 4) It is an off-white crystalline powder, relatively insoluble in water, and ... 1,4-Butanediol (BDOH, 0.998 mass fraction purity),...
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Solubility of Etoricoxib in Aqueous Solutions of 1,4-Butanediol, 1,4Dioxane, N,N‑Dimethylacetamide, N,N‑Dimethylformamide, Dimethyl Sulfoxide, and Ethanol at 298.2 K Pavan Rathi,*,† Abolghasem Jouyban,‡,§ Maryam Khoubnasabjafari,∥ and Mayura Kale⊥ †

Y B Chavan College of Pharmacy, Rauza Bagh, Aurangabad, Maharashtra, India 431001 Drug Applied Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz 51664, Iran § Pharmaceutical Engineering Laboratory, School of Chemical Engineering, College of Engineering, University of Tehran, P. O. Box 11155/4563, Tehran, Iran ∥ Tuberculosis and Lung Disease Research Center, Tabriz University of Medical Sciences, Tabriz 51664, Iran ⊥ Government College of Pharmacy, Osmanpura, Aurangabad, Maharashta, India 431001 ‡

ABSTRACT: Models for predicting the solubility of drugs in monosolvents and their mixtures have a practical importance in design and development of new products in pharmaceutical industries. Thus, present investigation pertains to the utility of a correlative model for solubility prediction of etoricoxib (ETR). The molar solubilities of ETR in a number of monosolvents and various mass fractions of their binary aqueous solvent mixtures were determined using the shakeflask method at 298.2 K. Densities of ETR saturated solutions in the monosolvents and their binary solvent mixtures were measured and then correlated using a well-established method proposed by Jouyban and Acree. Overall mean percentage deviations (OMPDs) between experimental and predicted values were 3.4 % for the molar solubilities and 0.1 % for the densities of the saturated solutions.

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INTRODUCTION Etoricoxib (ETR, Figure 1), a nonsteroidal anti-inflammatory drug, has both oral and injection dosage forms for commercial

devoid of information about physicochemical properties such as solubility. Aqueous solubility is one of the major challenges in the early stages of drug discovery, and any attempt to increase and predict the solubility is of utmost importance in the pharmaceutical industry.7 However, various leading pharmaceutical companies would have been able to triumph over technical hitches with very slightly aqueous soluble drugs; those with aqueous solubility of less than 0.1 mg·mL−1 present some unique challenges.8 Cosolvency, pH adjustment, surfactant addition, and complexation are the most commonly encountered pharmaceutical approaches for solubilizing drug candidates with low aqueous solubility.9−11 One of the most powerful and effective tools for increasing solubility of poorly water soluble drugs is mixing a safe and miscible cosolvent with water.12 Solubility determination of drugs in water−cosolvent mixtures provides useful data for better understanding of the solubility phenomenon in these media. Apart from experimentation works, the mathematical representation of solubility phenomenon is of value in prediction13 and accurate description of data and is of importance in different

Figure 1. Chemical structure of etoricoxib.

use in the treatment of chronic rheumatic disorders, usually administered at a dose of (60 to 120) mg daily.1 According to the biopharmaceutical classification system (BCS),2 ETR is a class II drug because it does not meet the current FDA criteria for high solubility to be classified as a class I drug.3,4 It is an offwhite crystalline powder, relatively insoluble in water, and shows pH-dependent solubility.5 Very low solubility of ETR restricts its therapeutic use. As per a literature survey, ETR had not been official in any Indian, British, United States, and Japanese pharmacopoieas until 2010. Even though ETR is official in Indian pharmacopoeia in 2014,6 it is completally © 2015 American Chemical Society

Received: March 4, 2015 Accepted: May 29, 2015 Published: June 22, 2015 2128

DOI: 10.1021/acs.jced.5b00201 J. Chem. Eng. Data 2015, 60, 2128−2134

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Table 1. Experimental Molar Solubilities, Csat m,T, of Etoricoxib in Aqueous Solutions of BDOH, 1,4-Dioxane, DMA, DMF, DMSO, and EtOH 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 (m1) Fractions of Solvent (1) Indicated by (1) density

density m1

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

0.858 1.64 2.99 5.83 14.6 39.3 110 305 631 792 686

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.858 1.55 3.15 6.00 12.7 32.9 109 306 626 898 695

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.858 1.77 2.85 6.01 12.8 33.2 99.1 283 623 858 701

0.00 0.10

0.858 1.82

100RSD

103(Xsat m,T)

BDOH (1) + Water (2) 1.07 0.0156 1.63 0.0322 1.01 0.0641 0.58 0.1374 0.12 0.3831 0.14 1.172 0.39 3.826 0.20 13.36 0.07 37.48 0.38 62.94 0.18 72.26 1,4-Dioxane (1) + Water (2) 1.07 0.0156 0.59 0.0302 0.31 0.0666 0.41 0.1393 0.18 0.3290 0.35 0.9644 0.90 3.774 0.08 13.22 0.37 36.85 0.20 74.32 0.20 73.01 DMA (1) + Water (2) 1.07 0.0156 0.88 0.0348 1.27 0.0620 1.39 0.1450 0.44 0.3461 1.18 1.032 0.85 3.655 0.18 13.21 0.10 40.46 0.04 77.84 0.30 81.12 DMF (1) + Water (2) 1.07 0.0156 0.17 0.0358

(g·cm−3)

m1

RSD

0.9948 0.9989 1.0021 1.0077 1.0122 1.0211 1.0277 1.0323 1.0377 1.0426 1.0398

0.0003 0.0010 0.0011 0.0012 0.0006 0.0019 0.0145 0.0195 0.0133 0.0833 0.0345

0.9948 1.0031 1.0127 1.0207 1.0282 1.0329 1.0358 1.0372 1.0353 1.0321 1.0268

0.0003 0.0003 0.0003 0.0009 0.0008 0.0041 0.0335 0.0073 0.0656 0.0486 0.0383

0.9948 0.9929 0.9867 0.9815 0.9772 0.9709 0.9645 0.9589 0.9527 0.9478 0.9427

0.0003 0.0006 0.0013 0.0031 0.0021 0.0145 0.0307 0.0178 0.0189 0.0109 0.0645

0.9948 0.9917

0.0003 0.0001

103(Csat m,T)

0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

3.40 5.78 13.4 38.5 110 293 644 926 708

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.858 1.61 3.14 5.97 12.7 38.8 97.8 317 653 886 703

0.00 0.10 0.20 0.30 0.40 0.50 0.60 0.70 0.80 0.90 1.00

0.858 1.87 3.96 7.97 16.7 42.2 139 370 667 877 701

100RSD

103(Xsat m,T)

DMF (1) + Water (2) 0.61 0.0731 0.76 0.1372 0.20 0.3550 0.46 1.158 1.32 3.874 0.27 12.82 0.38 38.52 0.80 76.82 0.58 68.99 DMSO (1) + Water (2) 1.07 0.0156 1.34 0.0312 0.41 0.0657 0.61 0.1361 0.45 0.3200 0.67 1.096 0.92 3.182 0.15 12.72 0.19 34.76 0.95 61.26 0.24 60.44 EtOH (1) + Water (2) 1.07 0.0156 0.32 0.0364 0.37 0.0836 0.72 0.1839 0.89 0.4245 0.61 1.203 1.18 4.590 1.07 15.20 0.31 36.16 0.60 61.37 0.17 53.74

(g·cm−3)

RSD

0.9891 0.9832 0.9795 0.9742 0.9692 0.9637 0.9598 0.9555 0.9527

0.0008 0.0016 0.0010 0.0063 0.0503 0.0260 0.0713 0.1996 0.1176

0.9948 1.0085 1.0179 1.0288 1.0402 1.0498 1.0609 1.0748 1.0842 1.1138 1.1056

0.0003 0.0008 0.0004 0.0013 0.0019 0.0086 0.0289 0.0137 0.0325 0.2090 0.0428

0.9948 0.9895 0.9725 0.9585 0.9412 0.9234 0.9055 0.8860 0.8637 0.8491 0.8199

0.0003 0.0002 0.0006 0.0022 0.0058 0.0102 0.0641 0.1443 0.0693 0.1687 0.0420

a

Data are the average of three determinations. RSD: relative standard deviation. The relative standard uncertainty for the solubilities ur(X) = 0.009. The relative standard uncertainty for the densities is ur(ρ) = 0.0004, and the standard uncertainty for temperature is u(T) = 0.05 K.

pharmaceutical fields including the preformulation stage of a new drug as well as formulation of the liquid dosage forms.14,15 In addition to experimental efforts to determine the solubility in monosolvents and binary solvent mixtures, a number of cosolvency models were proposed to calculate the solubility values.16,17 Among the developed cosolvency models, the Jouyban−Acree model is the most simple, accurate, and versatile model and provides reasonable predictions of drug solubilities not only in aqueous mixtures of N,N-dimethylformamide (DMF),18 N-methyl-2-pyrrolidone,19 1,4-dioxane,20,21 ethanol (EtOH),22,23 ethylene glycols,24 propylene glycol,25 polyethylene glycol 200,26 and polyethylene glycol 40027 but also in multiple ternary solvent systems such as water− ethanol−propylene glycol,28,29 water−propylene glycol−polyethylene glycol 400 or 600,30 water−N-methylpyrrolidone− polyethylene glycol 200 or 400,31 and water−ethanol−polyethylene glycol 60032 at various temperatures. These findings

were also supported for the solubility of drugs in a given water−cosolvent mixture after training the model using a minimum number of experimental data points. This model provides accurate mathematical descriptions as well as shows the effect of both temperature and solvent compositions on the solute solubility. 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. To the best of our knowledge, no literature has been found about solubility prediction of ETR in monosolvents and binary solvent mixtures at 298.2 K to date. Therefore, the purpose of the present investigation is to determine the composition of mixed solvent systems as well as to find a means of predicting the solubility of ETR in each binary solvent systems by the Jouyban−Acree model. This investigation further aims for prediction of saturated solutions densities in selected binary 2129

DOI: 10.1021/acs.jced.5b00201 J. Chem. Eng. Data 2015, 60, 2128−2134

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solvent mixtures at 298.2 K. A model could be useful if equilibrium solubility estimation within 30% in uncertainty is allowed.33

EXPERIMENTAL SECTION Materials. A white crystalline powder of ETR (0.990 mass fraction purity, determined by high performance liquid chromatography, HPLC) was kindly supplied by the Dr. Reddy’s Laboratories Ltd., Hyderabad. 1,4-Butanediol (BDOH, 0.998 mass fraction purity), 1,4-dioxane (0.995 mass fraction purity), N,N-dimethylacetamide (DMA, 0.997 mass fraction purity), DMF (0.998 mass fraction purity), dimethyl sulfoxide (DMSO, 0.998 mass fraction purity), and EtOH (0.995 mass fraction purity) were purchased from Research Lab Fine Chemical Industry, Islampur. All reagents were of analytical grade and used as such without further purification. Double distilled, deionized water was used throughout the experimentation for the preparation of binary solvent mixtures. Apparatus and Procedures. Equilibrium solubility studies were performed according to a shake-flask method developed by Higuchi and Connors.34 Briefly, an excess of pure ETR powder was added to approximately 10 mL of monosolvents or each cosolvent mixture (prepared by mixing known masses of solvents) in stoppered glass flasks. The flasks with the solute− binary solvent mixtures were placed on a shaker equipped with thermostatically controlled water baths maintained at 298.2 (± 0.05) K for at least 3 days to reach the equilibrium. Previous studies showed that this time period was sufficient to ensure saturation equilibrium of solute at the same temperature and further this equilibrium time was validated by quantifying the solute concentrations up to obtained constant values.35 Once at equilibrium, saturated 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. 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 each aqueous binary solvent mixture. All of the experimental studies were the average of at least three repetitive experiments. The average relative standard deviation (RSD) is within ± 0.59 % with measured molar solubilities. The densities of the monosolvents, solute-free binary solvent mixtures, and the filtrates of saturated solutions were measured using a 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 molal scale. Calculation Procedures. To assess the accuracy of the proposed model, percentage mean deviations (PMD) between the predicted and observed (molar solubilities/densities) values were estimated using36,37 100 N

⎡ predicted − observed ⎤ ⎥⎦ observed

∑ ⎢⎣

RESULTS AND DISCUSSION

Experimental Data of Solubility and Density. Table 1 shows the experimental values of equilibrium solubility for ETR expressed as molar and mole fraction at definite mass fraction (m) in a number of monosolvents and binary solvent mixtures containing BDOH + water, 1,4-dioxane + water, DMA + water, DMF + water, DMSO + water, and EtOH + water at 298.2 (± 0.05) K at different compositions and their RSDs. Throughout this experimental work solvent 1 refers to cosolvents and solvent 2 is water such as BDOH (1) + water (2), 1,4-dioxane (1) + water (2), and many others. As per our findings, the solubility of ETR in the monosolvents decreases in the order DMF > DMSO > EtOH > DMA > 1,4-dioxane > BDOH > water. The average minimum molar equilibrium solubility (solvent 2) reported in this investigation is 0.858·10−3 mol·L−1. The maximum equilibrium solubility for ETR in binary aqueous mixtures is observed at 0.90 m1 (m1 is the mass fraction of cosolvent for all investigated binary solvent systems) in a range of (0.926, 0.898, 0.886, 0.877, 0.858, and 0.792) mol·L−1 and in the sequence DMF > 1,4-dioxane > DMSO > EtOH > DMA > BDOH, 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 a maximum appeared at about 90% cosolvent concentration (0.90 m1). There are no published experimental data for ETR in the previously mentioned binary solvent systems. As per our interpretations it was found that upon addition of a small amount of less polar (solvent 1) to more polar solvent (solvent 2), a drastic increased in solubility (the difference of the molar concentrations at saturation) is observed in 0.90 m1 of solvent 1 in the series of the mass fraction between 0.0 and 1.0 of the less polar solvent, independent of the nonpolar (1,4-dioxane), semipolar (EtOH), and relatively polar (DMSO) binary solvent systems. This could be further explained by polarity of solvent 1, for, e.g., DMF and DMSO have higher values of the dipole moment of the water molecule (twice that of water). Careful examination of reported solubility data in Table 1 revealed that if solvent 1 is added to solvent 2, equilibrium molar solubility is increased very markedly (whereas at a very low level) at mass fraction of 0.1 from 0.858·10−3 (water) to 1.55·10−3 (1,4dioxane), 1.61·10−3 (DMSO), 1.64·10−3 (BDOH), 1.77·10−3 (DMA), 1.82·10−3 (DMF), and 1.87·10−3 (EtOH). Approximate an 825-fold increase in solubility is observed in monosolvent 1 (DMF, m1 = 1.00) in comparison to water. Such behavior is also prominent at the same mass fraction in the rest of the investigated solvents 1 in comparison to solvent 2 (water). An approximate 1080-fold increase in molar solubility is obtained upon addition of DMF (0.90 m1) 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 rest of the investigated binary solvent systems. In addition, these investigated cosolvent systems could be worked by reducing the interfacial tension between the aqueous solution and hydrophobic solute such as ETR and by this means disrupting the water’s self-association and prevents the ability of water molecules to squeeze out ETR from its three-dimensional structure, thereby increasing solubility.

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PMD =

Article

(1)

where N is the number of experimental data points in each set of binary solvent systems. It is obvious that lower PMD values will indicate higher prediction capability of the model. All computations were performed using various statistical software such as SPSS 11.5 and MS-Excel. 2130

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Table 2. Constants of the Jouyban−Acree Model for Back-Calculation of Solubility of Etoricoxib in Binary Solvent Mixtures According to Equation 2 (N, Number of Data Points; PMD, Percentage Mean Deviation; SD, Standard Deviation) solvent systems

N

A0

A1

A2

PMD

SD

BDOH + water 1,4-dioxane + water DMA+ water DMF + water DMSO + water EtOH + water

11 11 11 11 11 11

50.411 −15.066 −33.835 27.998 28.212 189.234

857.561 895.914 854.981 871.254 899.475 850.830

645.048 876.926 908.026 977.027 849.204 905.940

2.8 3.6 2.3 2.9 4.1 4.6

3.0 2.4 2.0 2.4 3.2 3.1

3.4

2.7

overall:

Equation 2 was used to fit the experimental (observed) solubility data of ETR in investigated binary solvent mixtures as shown in Table 1. The resulting model constants along with the PMD values were computed and given in Table 2. By using 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, i.e., sat the values for Xsat 1,T and X2,T (the data for m1 = 0.00 and m1 = 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 predicted and observed data was expressed by the PMD values as defined in eq 1. As a result, the best agreement, indicated by the lowest PMD value, is observed for DMA + water mixtures with 2.3 % (± 2.0 SD), the highest PMD value is found for EtOH + water mixtures with 4.6 % (± 3.1 SD). The overall PMD (OPMD) value (the mean of all values) is 3.4 % (± 2.7 SD). In Figure 2, the experimentally measured solubilities were plotted vs those recalculated by the aid of the Jouyban−Acree

Table 1 also reports the measured densities of the solute saturated solutions together with their RSDs. 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 the cost of experimental efforts. Values of densities for monosolvents are all in the relatively small range of (0.8199, 0.9427, 0.9527, 0.9948, 1.0268, 1.0398, and 1.1056) g·cm−3 respectively for EtOH, DMA, DMF, water, 1,4-dioxane, BDOH, and DMSO. Maximum saturation solution density values were obtained at 0.70 m1 for 1,4-dioxane + water and 0.90 m1 for BDOH + water and DMSO + water mixtures in a range of (1.0372, 1.0426, and 1.1138) g·cm−3, respectively, and follows the same trend as the monosolvents expected except EtOH + water, DMA + water, and DMF + water. This may be due to only a small difference in density values of these three monosolvents, which approximates the less mole fraction solubility. As per our expectations, these values are higher than those of the solutefree binary solvent mixtures. In both cases, the densities are uniformly continuous and nonlinear functions of the mass fraction without maxima in all the binary solvent systems studied except 1,4-dioxane + water. As mentioned earlier, this may be due to only a small difference in densities in monosolvents, for example, EtOH (0.8199 g·cm−3), DMA (0.9427 g·cm−3), DMF (0.9527 g·cm−3), and water (0.9948 g· cm−3), which follows unpredictable behavior in densities of mixtures of solvents studied. Computations of the Jouyban−Acree Model. Solubility. The model for representing the solubility of a solute in binary solvent mixtures at various temperatures is38 ⎡m m log X msat, T = m1 log X1,satT + m2 log X 2,satT + ⎢ 1 2 ⎢⎣ T

n

⎤

∑ Ai(m1 − m2)i ⎥ i=0

⎥⎦

(2)

where Xsat m,T is the solute’s mole fraction solubility in the binary solvent mixtures at temperature T (K), m1 and m2 are the mass fractions of solvents 1 and 2 in the absence of the solute, Xsat 1,T and Xsat 2,T denote the mole fraction solubility of the solute in the monosolvents 1 and 2, respectively, and Ai are computational model constants (coefficients) in the present theoretical meaning because Ai is a function of interaction energies among two and three bodies, which in turn describe the attractions among the different molecules present in solution and estimated by no intercept least-squares regression analysis. This procedure produced more accurate correlations than any other method for the solute’s solubility in aqueous binary solvent systems.39 The numerical values of n can be varied between 0 and 2 in accordance with accurate mathematical representation of the available experimental data sets.

Figure 2. Plot of calculated mole fraction solubility of etoricoxib in the investigated binary solvent mixtures against the corresponding experimental values at T = 298.2 K.

model. Because the solubilities vary over nearly 3 orders of magnitude, a logarithmic scale was chosen. A linear relation (R = 0.9999) 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 DMA + water mixtures. However, generally only slight scatter reflects the agreement between the two data sets, which by far suffices 2131

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Table 3. Model Constants of the Jouyban−Acree Model for the Back-Calculation of Density of Saturated Solutions of Etoricoxib in Binary Solvent Mixtures According to Equation 3 (PMD, Percentage Mean Deviation; SD, Standard Deviation; N, Number of Data Points) solvent systems

N

J0

J1

J2

PMD

SD

BDOH + water 1,4-dioxane + water DMA+ water DMF + water DMSO + water EtOH + water

11 11 11 11 11 11

1.466 11.354 1.276 0.301 −0.192 11.119

5.946 2.334 −2.118 −2.466 3.001 −0.660

3.316 −2.356 0.000 0.000 13.948 9.048

0.1 0.0a 0.0 0.0 0.2 0.1

0.0 0.0 0.0 0.0 0.3 0.2

0.1

0.1

overall: a

0.0 means < 0.05 %.

for the purpose to forecast the solubility of ETR in the binary solvents often used in practice. Density. The density data of the saturated solutions are required in some process designs40 and are also needed to convert the molar solubility to the mole fraction solubility or vice versa. The measured data for the density of the saturated solutions ρsat m,T of binary solvent mixtures (see Table 1) were fitted to eq 3: ⎡m m log ρmsat, T = m1 log ρ1,satT + m2 log ρ2,satT + ⎢ 1 2 ⎢⎣ T

n

⎤

i=0

⎥⎦

∑ Ji (m1 − m2)i ⎥ (3)

sat where ρsat 1,T and ρ2,T 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.41 These model constants are listed in Table 3 for all studied data sets (after excluding the constants with p > 0.10). The densities of the saturated solutions of ETR at any compositions of the binary solvent mixtures and temperatures could be interpolated using the reported model constants.42 Table 3 lists the numerical values of the constants of the Jouyban−Acree model for correlating density of the ETR saturated solution of the binary solvent systems and the obtained PMD values. The best correlation was observed for 1,4-dioxane + water mixtures with the PMD of < 0.05 % (± < 0.05 SD), and the worst one was obtained for DMSO + water mixtures with the PMD of 0.2 % (± 0.3 SD). The overall PMD of 0.1 % (± 0.1 SD) was obtained. The calculated densities were in good correlation with measured densities in investigated binary solvent mixtures (R = 0.999) and are shown in Figure 3.

calcd Figure 3. Calculated density (ρm,T ) of saturated solutions of −3 etoricoxib versus experimental values (ρexptl m,T ) (g·cm ) at T = 298.2 K.

acceptable range. The overall PMD (OPMD) values observed in these calculations show that the Jouyban−Acree model provides more accurate predictions in reported binary solvent systems for ETR, and these estimated differences could be acceptable at different stages of design and development of new products in pharmaceutical industries. The model could be used further for screening the experimental solubility data and saturated solution density data to detect possible outliers for redetermination and also predicting unmeasured solubilities and densities in different binary mixtures at various temperatures after successful training of the model using a minimum number of experimental data.

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CONCLUSIONS Experimental molar and mole fraction solubilities of ETR and saturated solution densities are reported in monosolvents and binary solvent mixtures of BDOH, 1,4-dioxane, DMA, DMF, DMSO, and EtOH with water at 298.2 K. These data, fit well by Jouyban−Acree model to calculate the solubilities and the densities at any composition of the binary solvent mixtures at fixed temperature, not only extend the available database of solubility data of pharmaceuticals which is in high demand in industry7 but could also be useful in selection of permissible solvents or their mixtures for liquid drug formulations such as injectables and orals. These findings were also supported by small PMD values of the back-calculated and experimental (observed) solubility and density data, which is within an

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Tel.:+91-9970669131. 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. 2132

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DOI: 10.1021/acs.jced.5b00201 J. Chem. Eng. Data 2015, 60, 2128−2134

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DOI: 10.1021/acs.jced.5b00201 J. Chem. Eng. Data 2015, 60, 2128−2134