Effects of grinding and humidification on the transformation of conglomerate to racemic compound in optically active drugs

Journal of Pharmacy and Pharmacology

Volumn 49, Issue 4, 1997, Pages 384-389

  Piyarom, Sujimon ^a   Yonemochi, Etsuo ^a   Oguchi, Toshio ^a   Yamamoto, Keiji ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LEUCINE; MALIC ACID; NORLEUCINE; SERINE; TARTARIC ACID; VALINE;

ARTICLE; CONTROLLED STUDY; CRYSTAL; DIFFERENTIAL SCANNING CALORIMETRY; DRUG MANUFACTURE; DRUG STORAGE; DRUG TRANSFORMATION; HUMIDITY; INFRARED SPECTROSCOPY; RACEMIC MIXTURE; STEREOISOMERISM; X RAY POWDER DIFFRACTION;

EID: 0030978350     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.2042-7158.1997.tb06811.x     Document Type: Article

References (30)

1. 3. Cryst. Struct. Commun. 1: 35-37
2. 2]Cl. Inorg. Chim. Acta 150: 75-80
3. di Blasio, B., Pedone, C., Sirigu, A. (1975) DL-leucine. Acta Crystallogr. Sect B 31: 601-602
4. Böcskei, Z., Kozma, D., Simon, K., Fogassy, E. (1995) Racemic compound formation-conglomerate formation. Part 2. Comparison of the optically active and racemic forms of α-phenylethylammonium oxalate. J. Chem. Res. (S): 160-161
5. Duddu, S. P., Grant, D. J. W. (1992) Formation of the racemic compound of ephedrine base from a physical mixture of its enantiomers in the solid, liquid, solution, or vapour state. Pharm. Res. 9: 1083-1091
6. Duddu, S. P., Vakilynejad, M., Jamali, F., Grant, D. J. W. (1993) Stereoselective dissolution of propranolol hydrochloride from hydroxypropyl methylcellulose matrices. Pharm. Res. 10: 1648-1653
7. Dwivedi, S. K., Sattari, S., Jamali, F., Mitchell, A. G. (1992) Ibuprofen racemate and enantiomers: phase diagram, solubility and thermodynamic studies. Int. J. Pharm. 87: 95-104
8. Eliel, E. L. (1962) Racemic modifications. In: Hume, D. N., King, E. L., Pople, J. A., Stork, G., Williams, H. H., Herschbach, D. R. (eds) Stereochemistry of Carbon Compounds, 1st edn. McGraw-Hill, New York, pp 43-47
9. Fassihi, A. R. (1993) Racemates and enantiomers in drug development. Int. J. Pharm. 92: 1-14
10. Harding, M. M., Howieson, R. M. (1976) L-leucine. Acta Crystallogr. Sect. B: 32: 633-634
11. Inagaki, M. (1977) Some aspects on the optical resolution by preferential crystallization based on phase equilibrium. Chem. Pharm. Bull. 25: 2497-2503
12. Jacques, J., Collet, A., Wilen, S. H. (1991) Binary mixtures of enantiomers. In: Jacques, J., Collet, A., Wilen, S. H. (eds) Enantiomers, Racemates, and Resolutions, 1st edn. Krieger, Florida, pp 32-130
13. Ketolainen, J., Poso, A., Viitasaari, V., Gynther, J., Pirttimäki, J., Laine, E., Paronen, P. (1995) Changes in solid-state structure of cyclophosphamide monohydrate induced by mechanical treatment and storage. Pharm. Res. 12: 299-304
14. Kimoto, H., Saigo, K., Ohashi, Y., Hasegawa, M. (1989) Molecular recognition in the formation of conglomerate crystal. 2. The role of arenesulfonic acid in the conglomerate crystals of amino acid salts. Bull. Chem. Soc. Jpn 62: 2189-2195
15. Kistenmacher, T. J., Rand, G. A., Marsh, R. E. (1974) Refinements of the crystal structures of DL-serine and anhydrous L-serine. Acta Crystallogr. Sect B 30: 2573-2578
16. Kozma, D., Böcskei, Z., Simon, K., Fogassy, E. (1994) Racemic compound formation-conglomerate formation. Part 1. structural and thermoanalytical study of hydrogen malonate, hydrogen phthalate and hydrogen succinate of α-phenylethylamine. J. Chem. Soc. Perkin Trans. 2: 1883-1886
17. Lambert, W. J., Timmer, P. G. (1991) Racemization of ibutilide in solution: a factor to consider when choosing to develop the racemate or a single enantiomer. Pharm. Res. 8: 1444-1447
18. Levy, R. H., Boddy, A. V. (1991) Stereoselectivity in pharmacokinetics: a general theory. Pharm. Res. 8: 551-556
19. Okaya, Y., Stemple, N. R. (1966) Refinement of the structure of D-tartaric acid by X-ray and neutron diffraction. Acta Crystallogr. 21: 237-243
20. Pirttimäki, J., Laine, E., Ketolainen, J., Paronen, P., (1993) Effects of grinding and compression on crystal structure of anhydrous caffeine. Int. J. Pharm. 95: 93-99
21. Repta, A. J., Baltezor, M. J., Bansal, P. C. (1976) Utilization of an enantiomer as a solution to a pharmaceutical problem: application to solubilization of 1,2-di(4-piperazine-2,6-dione)propane. J. Pharm. Sci. 65: 238-242
22. Shoemaker, D. P., Barieau, R. E., Donohue, J., Lu, C. (1953) The crystal structure of DL-serine. Acta Crystallogr. 6: 241-256
23. Sørensen, A. M. (1990) Requirements of the quality of chiral drug substances. Acta Pharm. Nord. 2: 181-184
24. Stern, F., Beevers, C. A. (1950) The crystal structure of tartaric acid. Acta Crystallogr. 3: 341-346
25. Torii, K., Iitaka, Y. (1970) The crystal structure of L-valine. Acta Crystallogr. Sect. B 26: 1317-1326
26. Torii, K., Iitaka, Y. (1973) Crystal structures and molecular conformations of L-methionine and L-norleucine. Acta Crystallogr. Sect. B 29: 2799-2807
27. Touitou, E., Chow, D. D., Lawter, J. R. (1994) Chiral β-blockers for transdermal delivery. Int. J. Pharm. 104: 19-28
28. Tsuboi, M., Takenishi, T., Iitaka, Y. (1959) Coexistence of two different molecular forms within a single crystal of L-valine. Bull. Chem. Soc. Jpn 32: 305-306
29. Vakily, M., Pasutto, F. M., Daneshtalab, M., Jamali, F. (1995) Inclusion complexation of heptakis(2,6-di-O-ethyl)-β-cyclodextrin with tiaprofenic acid: pharmacokinetic consequences of a pH-dependent release and stereoselective dissolution. J. Pharm. Sci. 84: 1014-1019
30. Van der Sluis, P., Kroon, J. (1984) Crystal structures of (-)-malic acid and of a second modification of (±)-malic acid. Acta Crystallogr. Sect. A 40 (suppl. index): C281