Characterization of tolbutamide polymorphs (Burger's forms II and IV) and polymorphic transition behavior

Journal of Pharmaceutical Sciences

Volumn 88, Issue 4, 1999, Pages 385-391

  Kimura, Kenya ^a   Hirayama, Fumitoshi ^a   Uekama, Kaneto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BUTANE; CARBONYL DERIVATIVE; CHLORPROPAMIDE; DICHLOROMETHANE; ORAL ANTIDIABETIC AGENT; SOLVENT; TOLBUTAMIDE; TOLUENE;

ANIMAL EXPERIMENT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DOG; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG SOLUBILITY; DRUG STORAGE; ENVIRONMENTAL TEMPERATURE; HUMIDITY; INFRARED SPECTROMETRY; MALE; NONHUMAN; ORAL DRUG ADMINISTRATION; PHASE TRANSITION; X RAY POWDER DIFFRACTION;

EID: 0032910069     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js980376z     Document Type: Article

References (27)

1. Haleblian, J.; McCrone, W. Pharmaceutical applications of polymorphism. J. Pharm. Sci. 1969, 58, 911-929.
2. Brittain, H. G.; Bogdanowich, S. J.; Bugay, D. E.; Vincentis, J. D.; Lewen, G.; Newman, A. W. Physical characterization of pharmaceutical solid. Pharm. Res. 1991, 8, 963-973.
3. Borka, L. Review on crystal polymorphism of substances in the european pharmacopoeia. Pharm. Acta Helv. 1991, 66, 16-22.
4. Shibata, M.; Kokubo, H.; Morimoto, K.; Morisaka, K.; Ishida, T.; Inoue, M. X-ray structural studies and physicochemical properties of cimetidine polymorphism. J. Pharm. Sci. 1983, 72, 1436-1442.
5. Matsuda, Y.; Kawaguchi, S.; Kobayashi, H.; Nishijo, J. Physicochemical characterization of spray-dried phenylbutazone polymorphs. J. Pharm. Sci. 1984, 73, 173-179.
6. Hirayama, F.; Usami, M.; Kimura, K.; Uekama, K. Crystallization and polymorphic transition behavior of chloramphenicol palmitate in 2-hydroxypropyl-β-cyclodextrin matrix. Eur. J. Pharm. Sci. 1997, 5, 23-30.
7. Thomas, R. C.; Ikeda, G. J. The metabolic fate of tolbutamide in man and in the rat. J. Med. Chem. 1966, 9, 507-510.
8. Simmons, D. L.; Ranz, R. J.; Gyanchandani, N. D.; Picotte, P. Polymorphism in pharmaceuticals II (tolbutamide). Can. J. Pharm. Sci. 1972, 7, 121-123.
9. Burger, A. Zur polymorphie oraler antidiabetika. Sci. Pharm. 1975, 43, 161-168.
10. Burger, A.; Ramberger, R. On the polymorphism of pharmaceuticals and other molecular crystals. II. Applicability of thermodynamic rules. Mikrochim. Acta 1979, 273-316.
11. Al-Saieq, S. S.; Riley, G. S. Polymorphism in sulphonylurea hypoglycaemic agents: I. Tolbutamide. Pharm. Acta Helv. 1981, 56, 125-129.
12. Leary, J. R.; Ross, S. D.; Thomas, M. J. K. On characterization of the polymorphs of tolbutamide Pharm. Weekblad. Sci. Ed. 1981, 3, 62-66.
13. Umeda, T.; Ohnishi, N.; Yokoyama, T.; Kuroda, T.; Kita, Y.; Kuroda, K.; Tatsumi, E.; Matsuda, Y. A kinetic study on the isothermal transition of polymorphic forms of tolbutamide and mefenamic acid in the solid state at high temperatures. Chem. Pharm. Bull. 1985, 33, 2073-2078.
14. Traue, J.; Kala, H.; Köhler, M.; Wenzel, U.; Wiegeleben, A.; Förster, B.; Pollandt, P.; Pintye-Hódi, K.; Szabó-Révész, P.; Selmeczi, B. Untersuchungen zur polymorphie von arzneistoffen in pulvern und tabletten. Pharmazie 1987, 42, 240-241.
15. Georgarakis, M. Untersuchungen zur polymorphie von tolbutamid. Pharmazie 1989, 44, 209-210.
16. Olives, A. I.; Martin, M. A.; del Castillo, B.; Barba, C. Influence of the presence of trace amounts of metals on the polymorphism of tolbutamide. Int. J. Pharm. 1996, 14, 1069-1076.
17. Stephenson, G. A.; Pfeiffer, R. R.; Byrn, S. R. Solid-state investigation of the tautomerism of acetohexamide. Int. J. Pharm. 1997, 146, 93-99.
18. The Japanese Pharmacopeia XIII; Japanese Pharmacopeial Conversion, Inc.: Tokyo, 1996; pp 116-121.
19. teXsan: Single-Crystal Structure Analysis Package, Vesion 1.6 (1993), Molecular Structure Corporation: The Woodlands, TX.
20. Ueda, H.; Nagai, T. Solid-state nuclear magnetic resonance spectroscopy and Raman spectroscopy of inclusion compound of tolbutamide with β-cyclodextrin. Chem. Pharm. Bull. 1981, 28, 1415-1421.
21. Carr, D. S.; Hariss, B. L. Solutions for maintaining constant relative humidity. Ind. Eng. Chem. 1949, 41, 2014-2015.
22. Nyqvist, H. Saturated salt solutions for maintaining specified relative humidities. Int. J. Pharm. Technol. Prod. Mfr. 1983, 4, 47-48.
23. Nogami, H.; Nagai, T.; Yotsuyanagi, Y. Dissolution phenomena of organic medicinals involving simultaneous phase changes. Chem. Pharm. Bull. 1969, 17, 499-509.
24. Donaldson, J. D.; Leary, J. R.; Ross, S. D.; Thomas, M. J. K. The structure of the orthorhombic form of tolbutamide (1-n-butyl-3-p-toluenesulphonylurea). Acta Crystallogr. 1981, B27, 2245-2248.
25. Rowe, E. L.; Anderson, B. D. Thermodynamic studies of tolbutamide polymorphs. J. Pharm. Sci. 1984, 73, 1673-1675.
26. Kimura, K.; Hirayama, F.; Arima, H.; Uekama, K. in preparation.
27. 3. J. Am. Ceram. Soc. 1972, 55, 74-77.