Pharmaceuticals and related drugs - Analytical Chemistry (ACS

Pharmaceuticals and Related Drugs Richard E. Huettemann,' Mary L. Cotter, and Charles J. Shaw Analytical Research Department, Division of Chemical Research, Ortho Pharmaceutical Corp., Raritan, NJ

C. A. Janicki, H. R. Almond, and E. S. Moyer Research Division, McNeil Laboratories, Inc., Fort Washington, PA

Arvin P. Shroff Food and Drug Administration, Rockville, MD

Frank Vestano Scientific and Mathematics Department, Johnson & Johnson Management lnformation Center, Raritan, NJ

This survey includes analytical methodology and subjects related to pharmaceutical analysis that have appeared in the literature during the period between June 1972 and June 1974. A cross reference to Chemical Abstracts (C.A.) or Analytical Abstracts (A.A.) was used to obtain the information included in this bibliography. The information has been arranged in tabular format and includes a class/compound table, a method/subject index, and a citation index by reference number. Subject 10, General Techniques, pertains to general methodology with no specific subject reference while the method/subject index for the other 9 subjects pertains to methodology specific for that subject. The survey indicates a substantial increase in the number of scientific publications and review articles that are of interest t o scientists working in this area of research. 1

Author to whom correspondence should be addressed

Gas-liquid and thin layer chromatographic methods continue to be very popular means for analyzing specific drugs. Analysts, however, appear to be reluctant to publish using the relatively new analytical tool, high pressure liquid chromatography. Spectrophotometric and volumetric methods continue to be popular while neutron activation analysis continues to become more popular for analyzing inorganics. References pertaining to mass spectrometry and GC-MS are increasing in number. The importance to the pharmaceutical industry of analyzing drugs in physiological fluids has been reflected by a substantial increase in the number of references related to this area. Authors have not been supplied with free reprints for distribution. Extra copies of the review issue may be obtained from Special issues Sales, ACS, 1155 16th St., N.W., Washington, DC 20036. Remit $4 for domestic U.S. orders; add $0.50 for additional postage for foreign destinations.

T a b l e I. Alkaloids Alkaloidal A m i n e s E p h e d r a Alkaloids Ephedrine

Me thylephedrine Alkaloids. General Method

C h r o m a t o g r a p h y Thin - L a ye r Automated A n a l y s i s Chromatography Gas C h r o m a t o g r a p h y Thin - L a y e r C h r o m a t o g r a p h y Ion -Exchange Colorimetric Differential Identification Mass Spectrometry Spectrophotometric Ultraviolet V o l u m e t r i c Acid - B a s e Nonaqueous Volumetric Argentimetric Chromatography Gas Spe c t r o pho t o m e t r i c U1t r a v i o 1e t Chromatography Gas Chromatography Gas -Mass Spectrometry Chromatography Thin-Layer Chromatography Chromatography Chromatography Colorimetric Complex Nletric Conductometric Dialysis

Paper Ion-Exchange H i g h - p r e s s u r e Liquid Titration

172 269 17. 18. 19. 74. 311. 353. 358. 369 49. 239. 311 135 48. 60, 286 1

311 204 334 48. 263 278 369 159 148 138 40. 44. 46. 82. 83. 136. 144. 197, 228. 229. 230. 296 83. 154. 265 147 92 2. 114. 180, 310 112 183 2

ANALYTICAL CHEMISTRY, VOL. 4 7 , NO. 5. APRIL 1975

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Richard E. Huenemann is a Scientist in the Analytical Research Group, Division Of Chemical Research. at Ortho Pharmaceutical Corp., Raritan, NJ. He graduated from the C i i College 01 New York in 1962 and was employed as an analytical Chemist at ClBA Pharmaceutical. Summit. NJ. from 1962-66. He is the coauthor of several publications. His fieids of interest include analytical methadaiagy. drug metabolism. bioavailabiiity-bioequivalency studies. physical and chemical properties Of drugs, Spectra interpretation. and natural product research. He is a member of the American Chemical Society and the American Pharmaceutical Association. * Author to whom reprint requests should be directed.

Mary Lou CDner is a Scientist In Analyticai Research at Ortho Pharmaceutical Corp.. Raritan. NJ. She received her Ph.0. in organic chemistry in 1971 from Stevens Institute Of Technology, Hoboken, NJ. She was a postdoctoral feiiow at the Institute for Steroid Research at Montefiore Hospital and Medical Center. Bronx. New York City and the Belfer Graduate School of Yeshiva University, New Yark Ci. She is the coauthor Of several publications and five patents. Her field of interest is slwo tural elucidation by spectroscopy. particuiariv PMR and CMR.

Ernest S. Moyer is a senior research chemist in the Basic Pharmacy Section at McNeii Laboratories Incorporated, Fort Washington. Pa. He received his E.S. degree from Juniata COllege in 1967 and the Ph.D. degree in Analytical Chemistry from West Virginia University in 1970. He was with the Celanese Research Corporation, Summit. NJ. from 1970-72 and was a Scientist at Ortho Pharmaceutical Carporation, Raritan. NJ, from 1972-74. His interests are in the area of drug analysts and new drug formulations. He is a member of the American Chemical Society and Phi Lambda UDsilOn.

Caslrnir A. Janicki is Section Head of the Analytical Pharmacy Section in the Pharmacy Research Department at McNeli Laboratories. He received his B.S. degree in chemistry from LaSalle College, Philadelphia. and his M.S. degree in analytical chemistry from Marquette University. He was employed as an Analytical Chemist at Smith Kline 8 French Laboratories in the Analytical 8 Physical Chemistry Section from 1957-60, and was awarded the Karr Fellowship from Smith Kline & French Laboratories for graduate studies in 1960. Dr. Janicki Obtained his Ph.0. degree in analvtical Chemistrv from Lovola University, Chicago. and joined McNeil Laboratories in 1963 as a Senior Research Chemist. He is presently responsible lor analytical research and development as well as the designing of stability studies for pharmaceuticals. His most recent studies include the application 01 high pressure liquid Chromatography to pharmaceutical analysis and thermal methods for assessing the purity of pharmaceuticals. Dr. Janicki is a member of the American Pharmaceutical Association and the Academy of Pharmaceutical Sciences.

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Charles J. Shaw is a Scientist in the Analyticai Research Group. Division of Chemical Research, at Ortho Pharmaceutical Corp.. Raritan. NJ. He graduated from LaSalle College in 1959 and received his M.S. from St. Joseph's College in 1969. He has had experience in analytical methods development for the pharmaceutical and chemical industry and is presently r e sponsible for the mass Spectrometry labratory. His area Of interest includes metabolism, analytical separation methods, and Structural elucidation using spectral techniques. He is a member of the American Chemical Society and the Scientific Research Society of America. He is also the coauthor of severai publicatlans.

Harold R. Almond, Jr., Grdup Leader a1 Analytical Chemistry in the Research Division of McNeii Laboratories. Rc.. received his B.S. and Ph.0. (1961) degrees in organic chemistry from the California bstitute of Technology. After joining McNeil Laboratories in 1960, his interests shined to analytical chemistry. in particular. to Structure determinations of new drug Substances using inStrumenta1 methods. Other interests include quantitative strutture-activity correlations and computer data acquisition and processing. He is a member Of the American Chemical Society. the American Society for Mass Spectrometry and an associate member Of Sigma Xi.

Frank L. Vestan0 is a Computer Systems Analyst, Scientific and Mathematics Oepartment, Johnson 8 Johnson Management information Center, Raritan. NJ. He received his B.S. in Science in 1973 at Stevens institute of Technology. While at Stevens, he became a member of the Khoda. Gear and Triangle, and Tau Beta pi honorary Societies and was nominated for the Oanforth Fellowship in his Senior year for his achievements as a mathematics student. He was also listed in the 1973 edtion of "Who's Who Among Students at American Colleges and Universities."

Arvln P. Shroll, a chemist at Food and Drug Administration, received his Ph.0. in pharmaceutical Chemistry from the University of Maryland. He has done postdoctoral work at the University of Maryland and was an instructor in chemistry. University College, University 01 Maryland, Baltimore. MD. Dr. Shroff was associated w i n Ortho Pnarmnceit cal Corporamn from 1963-74 as Group .eader n m e 01"1s On 01 Cnem Ca Research rlm research interests have been in medicinal chemistry. analytical Chemistry, pharmaceutical chemistry and biological sciences, and he has authored more than 45 scientific pa~ e r sand mtents. Dr. Shroff has co-auihored a chapter in e forthcoming issue of "Analytical Profiles Of Drug Substances." In 1972. Johnson & Johnson awarded him the Philip B. Hoffman award lor scientific exce1Ience. He has been an active member Of NJ-ACS and has held the following offices: CounsellorRaritan Valley ACS (1965-66): Cornmiheeman. NJ ChromatographyDiscussion Group (1967-69): Secretary (1969-70): Chairman-Elect (1970-71): Chairman (1971-72): Chairman-Elect Analytical Topical Group (1970-71) and Chairman (1971-72). Dr. Shroff was a member Of the Governing Board of the Eastern Analytical Symposium (now a member Of FACSS) and is a member of the editorial board of the Journalof Chmmafographic Sciences. He is ais0 a member Of the American Chemical Society. American PharmaceuticalAssociation. Society Of Applied SpectresCOPY. American Microchemical Society, Rho Chi, and Sigma Xi.

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Tabie X (Continued) (169) Staroscik. R., Manczyk, R.; F a r m . Pol.; Vol.:0028 Page:1151 Issue:12 Y r . : 7 2 CA. 79 0099305. (170) Staub, H., P e r r o n , W.; Anal. Chem.; Voi.:0046 Page:0128 Issue: Yr.:74 CA. 80 078138X. (171) Stefek, S.. Zahradnicek, M.; Cslka. F a r m . ; Vol.:0022 Pase:0158 Issue: Yr.:13 AA, 25 003365. (112) Subert, J.; Farmaceutickv. Obz.; Vol.:0041 Page:0445 1ssue:lO Yr.:72 AA. 2 4 003690. (173) Takacs, M.; Gvogyszereszet; Vol.:0016 Page:0281 Issue:08 Yr.:72 CA. 7 1 130634K. (174) Teodorescu, N.; Lucr. Coni. S a t . Chim. Anal.; Vol.:0003 Page:0337 Issue: Yr.:71 CA, 7 7 009608B. (179) T e s i o , O., Nikolic, K.; Arh. F a r m . ; Vol.:OO22 ?age:0217 Issue:O4 Y r . : 7 2 CA. I 9 1396631. (176) Thieieninnn, H.; Scientia. Pharm.; Vol.:0040 Page:0058 Issue: Yr.:l2 AA, 23 003436. (177) T r e i b e r , L. R., Oertengren, B., Lindsten, R.. Oertegren. T.; J . Chromatop’.; Vol.:0013 Page:0151 Issue: Yr.: 7 2 A A . 25 000558. (178) Tsunnkauw, N.; Chem. P h a r m . Bull. Tokyo; Vol.:OO19 P a ~ e : 2 5 7 91 s s u e : l l Yr.:71 AA. 23 001807. 1179) Tuckprrnan . M. M.. Ace1 K.. B i c a n - F i s t e r . T.. Billmi, J., Gibbs. I. S.; J. P h a r m . Sci.; Vol.:0061 Paee.0448 Issue: Y r . : 7 2 A A . 23 003440. (180) Tcihak, E , , Held, G.; P r o g r . Thin L a y e r Chroniatogr. Reiat. Methods. Vol:OO02 Page.0183 Issue: Yr:7l CA. 77 0248339. (181) Leda, F . ; Vitamins; Voi.:0047 Page:0529 Issue: Yr.:73 C A , 80 014353R. (1821 Vandeneeckhout, E., Denioerloose, P.; P h a r m . Weekbl. Ked.: Vol.:OIO6 Pace:0749 Issue:40 Yr.:71 A A . 23 000714. 0023 Issue: Y r . : 7 2 CA. 7 8 115253K. (183) Varda. S. P . ; Ervpt. P h a r m . J.; Vol.: (184) Vegh. A , ; Gvopvszereszet; Vul.:OO17 Issue:O3 Yr.:73 CA, 79 023597V. 12 Pace:0233 1ssue:OB Yr.:72 A A , 23 002712. (185) Wagner, P., Schuflels. P . ; Dt. Apothz (186) Wani, K . T.. Weinstein, B.; ?roc’. Thin Laver Chroniatogr. Relnt. Methods: Vul.:0003 Page:0177 Issue: Yr.:72 C A . 7 6 145201V. (187) Want. R. T., T s a i , Y. H.,Fuh, T . J.: Cheniistri Taikei; Vol.: Pa:e:0013 1ssue:Ol Yr.:72 AA, 24 003704. (1881 Wasternack. C . ; P h a r m a z i e ; Vol.:0027 Paee:0061 Issue: Yr.:72 AA. 23 002378. (189) Westgard, J . O., Lahnieyer, B. L . ; Cltn. C h e n . ; Vol.:OO18 Pare:0340 Issuc:04 Yr.:72 AA. 24 002887. (1901 U’ragg. J . S . : P h a r m . 3.; Vol.:0209 Pase.0611 Issue. Yr.:72 AA. 25 000410. (191) Wrasp. J . S.; P h a r m . J.; Vol.:O211 Pace:0192 Issue: Yr.:73 CA. 80 041065V. (192) W r a e g . J . S . ; Pharni. J.; Vol.:O2ll P a ~ e : 0 5 6 5Issue: Yr.:73 CA. 80 112690H. (193) Zacek. H.; Cslka. F a r m , ; Vol.:OO22 Pai.e.0126 Issue:03 Yr.:73 AA, 25 002536. (l(14) Zadeczky, S . ; Acta. P h a r m . Hung.; Vol.:0043 Pnge:0033 Issue: Yr.:13 AA, 2 5 001849. (195) Zadetzky, S., Kuttel. D., S r i r e t v a r v , 31.; Acta. P h a r m . Hunr.: Vol.:0042 Pace:0007 1ssue:Ol Y r . : 7 2 AA. 23 004126. (1861 Z a p c . M., Ksiezniakienicz, B.; F a r m . Pol., Vol.:OO28 Pace:O959 1ssue:lO Y r . : 7 2 CA, 7 8 047857K. (197) Zlatkis, A , , Bertsch, W., Lirhtenstein. H . A , . Tishbee. A , , Shumbo, F . . Liebich, H . X l , ; Annl. Chem.; Vol.: 0045 Page:0763 Issue:04 Yr.:73 A A , 24 003208. ~~

~

Analysis of High Polymers John Mitchell, Jr., and Jen Chiu Plastics Department, E. 1. du Pont de Nemours &

Co.,Inc., Wilmington, DE 79898

This review covers published general developments in analysis of polymers during the period November 1972 to November 1974. Emphasis is on techniques useful for assigning chemical and physical structure primarily associated with characterization of synthetic high polymers. An increasing number of books has been published covering general and specific areas. Mandelkern ( 6 6 ) provided an introduction to polymers, and Saunders (108) discussed the organic chemistry of adhesives, fibers, paints, plastics, and rubbers. Wunderlich (130) published the first of a series on macromolecular physics covering crystal structure, morphology, and defects. Polymer physics of glossy or amorphous macromolecules was reviewed with respect to thermodynamics, morphology, dynamic mechanical behavior, and diffusion ( 3 4 ) . Numerous books were devoted to polymer science. Collins, Bares, and Billmeyer, Jr. ( 1 4 ) described effective laboratory courses in synthesis and characterization of polymers with emphasis on the latter. It is a timely update of Billmeyer’s textbook published in 1971 ( 6 ) . Kirshenbaum (57) provided graded questions and problems in his study guide. Volume 1 2 of Advances in Polymer Science was published ( 1 1 ) . Progress in Polymer Science in Japan, volume 1 Authors have not been supplied with free reprints for distribution. Extra copies of the revlew issue may be obtalned from Special Issues Sales, ACS, 1155 16th St., N.W., Washlngton, DC 20036. Remlt $4 for dornestlc U.S. orders; add $0.50 for additlonai postage for foreign destlnatlons.

of which was published in 1971 (41), was continued through volume 6 published in 1973 (39, 40, 42, 47, 88,89). Volume 16 on reports on progress in polymer physics in Japan was published in 1973 ( 4 6 ) . Polymer materials science was reviewed by Schultz (111) and in two volumes edited by Jenkins (47, 48). Guillet ( 2 9 ) edited a publication on polymers and ecological problems based primarily on a symposium sponsored by three ACS Divisions and the National Academy of Sciences. International symposiums under IUPAC sponsorship on macromolecular science were held in Prague (113) and Helsinki ( 3 1 ) . The second international symposium on polymer characterization was held in Seattle (118) while the ACS sponsored one meeting on interdisciplinary approaches to polymer characterization (15) and another on mechanical behavior of plastics (8). Chemical transformations of polymers was the subject of a IUPAC conference (102). Structure and properties of polymer films with extensive discussion of techniques was published in a book edited by Lenz and Stein ( 6 2 ) while van Krevelen (125) reviewed relationships between polymer properties and chemical structure. CRC Critical Reviews (110) contained chapters on scanning electron microscopy (Broers), surface analysis (van Oostrom), electron solid scattering (Duke), and recent advance in surface characterization involving Auger electron spectroscopy (Tracy and Burkstrand), wave induced desorption (Lichtman), thermal desorption and infrared (Greenler), and molecular


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Pharmaceuticals and related drugs - Analytical Chemistry (ACS

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