Enantiotropically related albendazole polymorphs

Journal of Pharmaceutical Sciences

Volumn 99, Issue 9, 2010, Pages 3731-3742

  Pranzo, Marco B ^a   Cruickshank, Dyanne ^b   Coruzzi, Massimo ^a   Caira, Mino R ^b   Bettini, Ruggero ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Albendazole; Crystal structure; Enantiotropy; Polymorphism; Solid state

Indexed keywords

ALBENDAZOLE; HYDROCHLORIC ACID; METHANOL; N,N DIMETHYLFORMAMIDE;

ARTICLE; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; ENANTIOMER; ENVIRONMENTAL TEMPERATURE; SOLID STATE; X RAY DIFFRACTION;

EID: 77956364065     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22072     Document Type: Article

References (39)

1. Cook GC. 1990. Use of benzimidazole chemotherapy in human helminthiases: Indications and efficacy. Parasitol Today 6:133-136. (Pubitemid 20131124)
2. Marriner S. 1986. Anthelmintic drugs. Vet Rec 118:181-184.
3. Gyurik RJ, Theodorides VJ. 1975. Methyl 5-propylthio-2- benzimidazolcarbamate. US patent, ed.: SmithKline Corporation.
4. O'Neil MJ, editor. 2006. The Merck Index. 40th edition. Whitehouse Station, NJ: Merch Research Laboratoires. p 39.
5. Torrado S, Torrado S, Torrado JJ, Caerdoniga R. 1996. Preparation, dissolution and characterisation of albendazole solid dispersions. Int J Pharm 140:247-250.
6. Del Brutto OH, Sotelo J, Roman GC. 1993. Therapy for neurocysticercosis: A reappraisal. Clin Infect Dis 17:730-735.
7. Batzias GC, Theodosiadou E, Delis GA. 2004. Quantitative determination of albendazole metabolites in sheep spermatozoa and seminal plasma by liquid chromatographic analysis with fluorescence detection. J Pharm Biomed Anal 35:1191-1202.
8. Swarnkar CP, Sanyal PK, Singh D, Khan FA, Bhagwan PS. 1998. Comparative disposition kinetics of albendazole in sheep following oral and intraruminal administration. Vet Res Commun 22:545-551.
9. Mirfazaelian A, Dadashzadeh S, Rouini MR. 2002. Effect of gender in the disposition of albendazole metabolites in humans. Eur J Clin Pharmacol 58:403-408.
10. Mirfazaelian A, Rouini MR, Dadashzadeh S. 2002. Dose dependent pharmacokinetics of albendazole in human. Biopharm Drug Dispos 23:379-383. (Pubitemid 36002137)
11. Alvarez LI, Sanchez SF, Lanusse CE. 1997. Modified plasma and abomasal disposition of albendazole in nematode-infected sheep. Vet Parasitol 69:241-253.
12. Prichard RK, Hennessy DR, Steel JW, Lacey E. 1985. Metabolite concentrations in plasma following treatment of cattle with five anthelmintics. Res Vet Sci 39:173-178. (Pubitemid 15237130)
13. Garcia JJ, Bolas-Fernandez F, Torrado JJ. 1999. Quantitative determination of albendazole and its main metabolites in plasma. J Chromatogr B 723:265-271.
14. Lindemberg M, Kopp S, Dressman JB. 2004. Classification of orally administered drugs on the World Health Organization Model list of Essential Medicines according to the biopharmaceutics classification system. Eur J Pharm Biopharm 58:265-278.
15. Torrado S, Torrado S, Caerdoniga R, Torrado JJ. 1996. Formulation parameters of albendazole solution. Int J Pharm 140:45-50.
16. Castillo JA, Palomo-Canales J, Garcia JJ, Lastres JL, Bolas F, Torrado JJ. 1999. Preparation and characterization of albendazole beta-cyclodextrin complexes. Drug Dev Ind Pharm 25:1241-1248.
17. Haleblian J, McCrone W. 1969. Pharmaceutical applications of polymorphism. J Pharm Sci 58:911-929.
18. Grant DJW. 1999. Theory and origin of polymorphism. In: Brittain GH, editor. Polymorphism in pharmaceutical solids, ed. New York: Marcel Dekker. pp. 1-33.
19. Vippagunta SR, Brittain HG, Grant DJW. 2001. Crystalline solids. Adv Drug Del Rev 48:3-26.
20. Nonius BV. 2002. COLLECT Nonius. Delft, the Netherlands: Nonius BV.
21. Otwinowski Z, Minor W. 1997. Processing of X-ray diffraction data collected in oscillation mode. In: Carter CW, Sweet RM, editors. Methods in enzymology, ed. New York: Academic Press. pp. 307-326.
22. Sheldrick G. 1990. Phase annealing in SHELX-90: Direct methods for larger structure. Acta Crystallogr A46:467-473.
23. Sheldrick GM. 1997. SHELX-97: Program for the refinement of crystal structures. University of Göttingen, Germany.
24. Spek AL. 1990. PLATON: A multipurpose crystallographic tool. Acta Crystallogr A46:C34.
25. 2008. Monograph 01/2008:1386. European Pharmacopoeia 6.0, ed. Strasbourg, France: EDQM. pp. 1122-1123.
26. Alanazi FK, El-Badry M, Ahmed MO, Alsarra IA. 2007. Improvement of albendazole dissolution by preparing microparticles using spray-drying technique. Sci Pharm 75:63-79. (Pubitemid 47057633)
27. Moriwaki C, Costa GL, Ferracini CN, de Moraes FF, Zanin GM, Pineda EAG, Matioli G. 2008. Enhancement of solubility of albendazole by complexation with b-cyclodextrin. Brazilan J Che Eng 25:255-267.
28. Kalaiselvan R, Mohanta GP, Manna PK, Manavalan R. 2006. Studies on mechanism of enhanced dissolution of albendazole solid dispersions with crystalline carriers. Indian J Pharm Sci 68:599-607.
29. Kalaiselvan R, Mohantha GP, Manna PK, Manavalan R. 2006. Multicoponent system of albendazole with cyclodextrins and hydroxyacids. Acta Pharm Sci 48:19-33. (Pubitemid 46211965)
30. Aguiar AJ, Zelmer JE. 1969. Dissolution behavior of polymorphs of chloramphenicol palmitate andmefenamic acid. J Pharm Sci 58:983-987.
31. Carstensen JT. 2001. Polymorphism. In: Carstensen JT, editor. Advanced Pharmaceutical Solids, ed. New York: Marcel Dekker. pp. 117-131.
32. Brittain HG, Grant DJW. 1999. Effect of polymorphism and solid-state solvation on solubility and dissolution rate. In: Brittain HG, editor. Polymorphism in pharmaceutical solids, ed. New York: Marcel Dekker. pp. 291-329.
33. Bettini R, Bonassi L, Castoro V, Rossi A, Zema L, Gazzaniga A, Giordano F. 2001. Solubility and conversion of carbamazepine polymorphs in supercritical carbon dioxide. Eur J Pharm Sci 13:281-286.
34. Sokol VI, Davydov VV, Porai-Koshits MA, Zaitsev BE, Palishkin MV, Sheban GV, Pakhomov VI, Kukalenko SS. 1988. Crystal and molecular structure of N-(2-benzimidazolyl)-O-alkyl carbamates. Izv Akad Nauk SSSR Ser Khim (Russ) (Russ Chem Bull) 37:1306-1311.
35. Iriepa I, Villasante FJ, Galvez E, Bellanato J, Martin A, Gomez-Sal P. 2004. Synthesis, spectroscopic and crystallographic study of some carbamates from an azabicyclic chloroformate and primary heterocyclic amines. New J Chem 28:618-624.
36. Blaton NM, Peeters OM, De Ranter CJ. 1980. (5-Benzoyl-1H-benzimidazol-2- yl)carbamic acid methyl ester hydrobromide (Mebendazole.HBr), C16H14BrN3O3. Cryst Struct Commun 9:181-186.
37. Sepassi K, Nichol GS, Yalkowsky SH. 2006. The napsylate salt of carbendazim. 2-(Methoxycarbonylamino)benzimidazolium naphthalene-1-sulfonate. Acta Crystallogr Sect E: Struct Rep Online E62:o5172-o5173.
38. Etter MC. 1990. Encoding and decoding hydrogen bond patterns of organic compounds. Acc Chem Res 12:120-126.
39. Yvon K, Jeitschko W, Parthe E. 1977. LAZY PULVERIX: A computer program for calculating X-ray and neutron diffraction powder patterns. J Appl Crystallogr 10:73-74.