The effect of temperature and moisture on the amorphous-to-crystalline transformation of stavudine

International Journal of Pharmaceutics

Volumn 379, Issue 1-2, 2009, Pages 72-81

  Strydom, Schalk ^a,b   Liebenberg, Wilna ^a   Yu, Lian ^b   de Villiers, Melgardt ^b  

^a NORTH WEST UNIVERSITY   (South Africa)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Amorphous; Hydrate; Moisture; Stability; Stavudine; Transformation

Indexed keywords

POLY(METHYL METHACRYLATE); STAVUDINE;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG COATING; DRUG STABILITY; MOISTURE; PHASE TRANSITION; PRIORITY JOURNAL; TEMPERATURE;

ANTI-HIV AGENTS; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; EXCIPIENTS; HUMIDITY; POLYMETHYL METHACRYLATE; STAVUDINE; TEMPERATURE;

EID: 68649093676     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.06.012     Document Type: Article

References (50)

1. Alneck C., and Zografi G. The molecular basis of moisture effects on the physical and chemical stability of drugs in the solid state. Int. J. Pharm. 62 (1990) 87-95
2. Andronis V., and Zografi G. Molecular mobility of supercooled amorphous indomethacin, determined by dynamic mechanical analysis. Pharm. Res. 14 (1997) 410-414
3. Andronis V., and Zografi G. Crystal nucleation and growth of indomethacin polymorphs from the amorphous state. J. Non-Cryst. Solids 271 (2000) 236-248
4. Bauer-Brandl A. Polymorphic transitions of cimetidine during manufacture of solid dosage forms. Int. J. Pharm. 140 (1996) 195-206
5. Bhugra C., and Pikal M.J. Role of thermodynamic, molecular, and kinetic factors in crystallization from the amorphous state. J. Pharm. Sci. 97 (2008) 1329-1349
6. Bowen A., Palasanthiran P., and Sohn A.H. Global challenges in the development and delivery of paediatric antiretrovirals. Drug Disc. Today 13 (2008) 530-535
7. Byakika-Kibwika P., Lamorde M., Kalemeera F., D'Avolio A., Mauro S., Di Perri G., Ryan M., Mayanja-Kizza H., Khoo S., Back D., Boffito M., and Merry C. Steady-state pharmacokinetic comparison of generic and branded formulations of stavudine, lamivudine and nevirapine in HIV-infected Ugandan adults. J. Antmicrob. Chemother. 62 (2008) 1113-1117
8. Burnett D.J., Thielmann F., and Booth J. Determining the critical relative humidity for moisture-induced phase transitions. Int. J. Pharm. 287 (2004) 123-133
9. Byrn S.R., Lin C.T., Perrier P., Clay G.G., and Sutton P.A. Solid state photooxidation of 21-cortisol tert-butylacetate to 21-cortisone. J. Org. Chem. 47 (1982) 2978-2981
10. Byrn S.R., Pfeiffer R.R., and Stowel J.G. Solid-State Chemistry of Drugs. 2nd ed. (1999), SSCI Inc., West Lafayette, IN pp. 461-460
11. Chien C.V. HIV/AIDS drugs for sub-Saharan Africa: how do brand and generic supply compare?. PLoS ONE 2 (2007) e278
12. Chieng N., Rades T., and Saville D. Formation and physical stability of the amorphous phase of ranitidine hydrochloride polymorphs prepared by cryo-milling. Eur. J. Pharm. Biopharm. 68 (2008) 771-780
13. Connors K.A., Amidon G.L., and Stella V.J. Chemical Stability of Pharmaceuticals: A Handbook for Pharmacists. 2nd ed. (1986), Wiley Interscience, New York
14. Craig D.Q.M., Royall P.G., Kett V.L., and Hopton M.L. The relevance of amorphous state to pharmaceutical dosage forms: glassy drugs and freeze dried systems. Int. J. Pharm. 179 (1999) 179-207
15. Dawoodbhai S., and Rhodes C.T. The effect of moisture on powder flow and on compaction and physical stability of tablets. Drug Dev. Ind. Pharm. 15 (1989) 1577-1600
16. De Villiers M.M. Influence of the cohesive behaviour of micronized drug powders on particle size analysis. J. Pharm. Biomed. Anal. 13 (1995) 191-199
17. De Villiers M.M., Terblanche R.J., Liebenberg W., Swanepoel E., Dekker T.G., and Song M. Variable temperature X-ray powder diffraction analysis of the crystal transformation of the pharmaceutically preferred polymorph C of mebendazole. J. Pharm. Biomed. Anal. 38 (2005) 435-441
18. De Villiers M.M., Van Der Watt J.G., and Lötter A.P. The interconversion of the polymorphic forms of chloramphenicol palmitate (CAP) as a function of temperature. Drug Dev. Ind. Pharm. 17 (1991) 1295-1303
19. De Villiers M.M., Van Der Watt J.G., and Lötter A.P. Influence of surfactants and interactive mixing on the cohesive properties of a poorly wettable solid. Powder Technol. 75 (1993) 159-165
20. Dunge A., Sharda N., Singh B., and Singh S. Establishment of inherent stability of stavudine and development of a validated stability-indicating HPLC assay method. J. Pharm. Biomed. Anal. 37 (2005) 1115-1119
21. Duse A.G., Morar A., Landman I., Vermaak W.J.H., Schoeman H., Kruger M.J., Janse van Rensburg E., Luthy R., and Singh S. Short-term effectiveness and safety of HAART in the form of a generic fixed-dose combination of stavudine, lamivudine and nevirapine (Triviro) in HIV-1-infected adults in Zimbabwe. S Afr. J. HIV Med. 9 (2008) 51-56
22. Fukuoka E., Midori M., and Shigeo M. Some physicochemical properties of glassy indomethacin. Chem. Pharm. Bull. 34 (1986) 4314-4321
23. Gandhi R.B., Bogardus J.B., Bugay D.E., Perrone R.K., and Kaplan M.A. Pharmaceutical relationships of three solid state forms of stavudine. Int. J. Pharm. 201 (2000) 221-237
24. Guo Y., Byrn S.R., and Zografi G. Physical characteristics and chemical degradation of amorphous quinapril hydrochloride. J. Pharm. Sci. 89 (2000) 128-143
25. Hancock B.C., and Parks M. What is the true solubility advantage for amorphous pharmaceuticals?. Pharm. Res. 17 (2000) 397-404
26. Hancock B.C., and Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci. 86 (1997) 1-12
27. Hosseinipour M.C., Corbett A.H., Kanyama C., Mshali I., Phakati S., Rezk N.L., Van der Horst C., and Kashuba A.D.M. Pharmacokinetic comparison of generic and trade formulations of lamivudine, stavudine and nevirapine in HIV-infected Malawian adults. AIDS 21 (2007) 59-64
28. Kaul N., Agrawal H., Paradkar A.R., and Mahadik K.R. The ICH guidance in practice: stress degradation studies on stavudine and development of a validated specific stability-indicating HPTLC assay method. J. Chromatogr. Sci. 43 (2005) 406-415
29. Kawaguchi T., Fukushima S., Ohmura M., Mishima M., and Nakano M. Enzymatic and chemical stability of 2′,3′-dideoxy-2′,3′-didehydropyrimidine nucleosides: potential anti-acquired immunodeficiency syndrome agents. Chem. Pharm. Bull. 37 (1989) 1944-1945
30. Konno H., and Taylor L.S. Influence of different polymers on the crystallization tendency of molecularly dispersed amorphous felodipine. J. Pharm. Sci. 95 (2006) 2692-2705
31. Konno H., and Taylor L.S. Ability of different polymers to inhibit the crystallization of amorphous felodipine in the presence of moisture. Pharm. Res. 25 (2008) 969-978
32. L'homme R.F.A., Dijkema T., Warris A., Van der Ven A.J.A.M., Gibb D.M., and Burger D.M. Pharmacokinetics of two generic fixed-dose combinations for HIV-infected children (Pedimune Baby & Pedimune Junior) are similar to the branded products in healthy adults. J. Antimicrob. Chemother. 59 (2007) 92-96
33. Laurent C., Kouanfack C., Koulla-Shiro S., Nkoue N., Bourgeois A., Calmy A., Lactuock B., Nzeusseu V., Mougnutou R., Peytavin G., Liegeois F., Nerrienet E., Tardy M., Peeters M., Andrieux-Meyer I., Zekeng L., Kazatchkine M., Mpoudi-Ngole E., and Delaporte E. Effectiveness and safety of a generic fixed-dose combination of nevirapine, stavudine, and lamivudine in HIV-1-infected adults in Cameroon: open-label multicenter trial. Lancet 364 (2004) 29-34
34. Laurent C., Kouanfack C., Koulla-Shiro S., Njoume M., Nkene Y.M., Ciaffi L., Brulet C., Peytavin G., Vergne L., Calmy A., Mpoudi-Ngole E., and Delaporte E. Long-term safety, effectiveness and quality of a generic fixed-dose combination of nevirapine, stavudine and lamivudine. AIDS 21 (2007) 768-771
35. Mirmehrabi M., Rohani S., Murthy K.S.K., and Radatus B. Polymorphic behavior and crystal habit of an anti-viral/HIV drug: stavudine. Cryst. Growth Des. 6 (2006) 141-149
36. Mirmehrabi M., Rohani S., and Perry L. Thermodynamic modeling of activity coefficient and prediction of solubility: part 2. Semipredictive or semiempirical models. J. Pharm. Sci. 95 (2006) 798-809
37. Mohammed G.A., Puri V., and Bansal A.K. Coprocessing of nevirapine and stavudine by spray drying. Pharm. Dev. Technol. 13 (2008) 210-299
38. Marcelin A., Jarrousse B., Derache A., Ba M., Dakouo M., Doumbia A., Haidara I., Maiga A., Carcelain G., Peytavin G., Katlama C., and Calvez V. HIV drug resistance after the use of generic fixed-dose combination stavudine/lamivudine/nevirapine as standard first-line regimen. AIDS 21 (2007) 2341-2343
39. Penzak S.R., Acosta E.P., Turner M., Tavel J.A., and Masur H. Analysis of generic nevirapine products in developing countries. JAMA 289 (2003) 2648-2649
40. Penzak S.R., Acosta E.P., Turner M., Tavel J.A., and Masur H. Antiretroviral drug content in products from developing countries. Clin. Infect. Dis. 38 (2004) 1317-1319
41. Petit S., and Coquerel G. The amorphous state. In: Hilfiker R. (Ed). Polymorphism in the Pharmaceutical Industry (2006), Wiley-VCH, Weinheim 259-285
42. Radatus, B.K., Murthy, K.S.K., 2003. Process for the preparation of substantially pure stavudine and related intermediates useful in the preparation thereof. US Patent 6,635,753.
43. Stephenson G.A., Groleau E.G., Kleemann R.L., Xu W., and Rigsbee D.R. Formation of isomorphic desolvates: creating a molecular vacuum. J. Pharm. Sci. 87 (1998) 536-542
44. Takeuchi H., Yasuji T., Yamamoto H., and Kawashima Y. Temperature- and moisture-induced crystallization of amorphous lactose in composite particles with sodium alginate prepared by spray-drying. Pharm. Dev. Technol. 5 (2000) 355-363
45. Tan S.B., and Newton M.B. Powder flowability as an indication of capsule filling performance. Int. J. Pharm. 61 (1990) 145-155
46. The United States Pharmacopeia. The United States Pharmacopeial Convention (2007), The United States Pharmacopeia, Rockville, MD
47. g. Pharm. Res. 23 (2006) 2350-2355
48. Wu T., Sun Y., Li N., De Villiers M.M., and Yu L. Inhibiting surface crystallization of amorphous indomethacin by nanocoating. Langmuir 23 (2007) 5148-5153
49. Yu L. Amorphous pharmaceutical solids: preparation, characterization and stabilization. Adv. Drug Deliv. Rev. 48 (2001) 27-42
50. Zhu L., Wong L., and Yu L. Surface-enhanced crystallization of amorphous nifedipine. Mol. Pharm. 5 (2008) 921-926