Progressive steps of polymorphic transformation of gabapentin polymorphs studied by hot-stage FTIR microspectroscopy

Journal of Pharmacy and Pharmaceutical Sciences

Volumn 13, Issue 1, 2010, Pages 67-77

  Hsu, Cheng Hung ^a   Ke, Wen Ting ^a   Lin, Shan Yang ^b  

^a Orient Pharma Co   (Taiwan)

^b YUANPEI UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

GABAPENTIN; 4 AMINOBUTYRIC ACID; AMINE; ANTICONVULSIVE AGENT; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE;

ARTICLE; CYCLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG TRANSFORMATION; INFRARED SPECTROSCOPY; SPECTROMETRY; TEMPERATURE DEPENDENCE; THERMOGRAVIMETRY; X RAY POWDER DIFFRACTION; CHEMISTRY; CRYSTALLIZATION; HEAT; METHODOLOGY; X RAY DIFFRACTION;

AMINES; ANTICONVULSANTS; CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; CYCLOHEXANECARBOXYLIC ACIDS; GAMMA-AMINOBUTYRIC ACID; HOT TEMPERATURE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMOGRAVIMETRY; X-RAY DIFFRACTION;

EID: 77955050963     PISSN: None     EISSN: 14821826     Source Type: Journal    
DOI: 10.18433/j3fs32     Document Type: Article

References (27)

1. Goa KL, Sorkin EM, Gabapentin. A review of its pharmacological properties and clinical potential in epilepsy. Drugs. 46: 409-427, 1993.
2. Dobecki DA, Schocket SM, Wallace MS. Update on pharmacotherapy guidelines for the treatment of neuropathic pain. Curr Pain Headache Rep. 10: 185-190, 2006.
3. Johnson RW, Wasner G, Saddier P, Baron R. Postherpetic neuralgia: epidemiology, pathophysiology and management. Expert Rev Neurother. 7: 1581-1595, 2007.
4. Moretti R, Torre P, Antonello RM, Cazzato G. Gabapentin as a possible treatment of behavioral alterations in Alzheimer disease (AD) patients. Eur J Neurol. 8: 501-502, 2001.
5. Ananda K, Aravinda S, Vasudev Prema G, Raja Muruga Poopathi K, Sivaramakrishnan H, Nagarajan K, Shamala N, Balaram P. Stereochemistry of gabapentin and several derivatives: Solid state conformations and solution equilibria. In: Current Science, 85: 1002-1011, 2003.
6. Bryans JS, Horwell DC, Ratcliffe GS, Receveur JM, Rubin JR. An in vitro investigation into conformational aspects of gabapentin. Bioorg Med Chem. 7: 715-721, 1999.
7. Sills GJ. The mechanisms of action of gabapentin and pregabalin. Curr Opin Pharmacol. 6: 108-113, 2006.
8. Yamauchi T, Kaneko S, Yagi K, Sase S. Treatment of partial seizures with gabapentin: double-blind, placebo-controlled, parallel-group study. Psychiatry Clin Neurosci. 60: 507-515, 2006.
9. Byrn SR, Pfeiffer RR, Stowell JG (eds.). Solid-state Chemistry of Drugs. 2nd Ed., SSCI, Inc., West Lafayette, Indiana, USA. 1999.
10. Byrn SR, Xu W, Newman AW. Chemical reactivity in solid-state pharmaceuticals: formulation implications. Adv Drug Deliv Rev. 48: 115-136, 2001.
11. US FDA. Guidance for Industry. ANDAs: Pharmaceutical. Solid Polymorphism. Chemistry, Manufacturing, and Controls Information. 2007.
12. Ciavarella AB, Gupta A, Sayeed VA, Khan MA, Faustino PJ. Development and application of a validated HPLC method for the determination of gabapentin and its major degradation impurity in drug products. J Pharm Biomed Anal. 43: 1647-1653, 2007.
13. Hsu CH, Lin SY. Rapid examination of the kinetic process of intramolecular lactamization of gabapentin using DSC-FTIR. Thermochimica Acta. 486: 5-10, 2009.
14. Pesachovich M, Singer C, Pilarski G. Preparation of gabapentin. US Patent 6255526, 2001.
15. Satyanarayana, C., Ramanjaneyulu, G. S., Kumar, I. V. S. Novel polymorph of gabapentin and its conversion to gabapentin Form-II. WO 2004/110342, 2004.
16. Kumar Y, Khanduri CH, Ganagakhedkar KK, Chakraborthy R, Dorwal HN, Rohatgia A, Panda AK. Crystalline gabapentin. WO 2004/106281, 2004.
17. Braga D, Grepioni F, Maini L, Rubini K, Polito M, Brescello R, Cotarca L, Duarte MT, André V, Piedade MFM. Polymorphic gabapentin: thermal behaviour, reactivity and interconversion of forms in solution and solid-state. New J. Chem., 32: 1788-1795, 2008.
18. Reece HA, Levendis DC. Polymorphs of gabapentin. Acta Cryst. C64: o105-o108, 2008.
19. Ibers J A. Gabapentin and gabapentin monohydrate. Acta Cryst. Cryst. Struct. Commun. 57C: 641-643, 2001.
20. Butler DE, Greenman BJ. Gabapentin monohydrate and a process for producing the same. US Patent 4894476, 1990.
21. Medichem SA, Bosch Illado J, Arnalot Aguilar C, Burgarolas Montero MC. Process and Methods for the Preparation of Gabapentin and Its Intermediates. WO2006090208, 2006.
22. Vasudev PG, Aravinda S, Ananda K, Veena SD, Nagarajan K, Shamala N, Balaram P. Crystal structures of a new polymorphic form of gabapentin monohydrate and the e and z isomers of 4-tertiarybutylgabapentin. Chem Biol Drug Des. 73: 83-96, 2009.
23. Wenger M, Bernstein J. An alternate crystal form of gabapentin: A cocrystal with oxalicaAcid. Cryst. Growth Des., 8: 1595-1598,2008.
24. Lin SY, Chien JL. In vitro simulation of solid-solid dehydration, rehydration, and solidification of trehalose dihydrate using thermal and vibrational spectroscopic techniques, Pharm. Res. 20: 1926-1931, 2003.
25. Wang SL, Lin SY, Hsieh TF, Chan SA. Thermal behavior and thermal decarboxylation of 10-hydroxycamptothecin in the solid sate J. Pharm. Biomed. Anal. 43: 457-463, 2007.
26. Cutrignelli A, Denora N, Lopedota A, Trapani A, Laquintana V, Latrofa A, Trapani G, Liso G. Comparative effects of some hydrophilic excipients on the rate of gabapentin and baclofen lactamization in lyophilized formulations. Int J Pharm. 332: 98-106, 2007.
27. Chimatadara SA, Basavaraja T, Thabaja KA, Sharanappa T. Ruthenium(III) catalysed oxidation of gabapentin (neurontin) by diperiodatocuprate(III) in aqueous alkaline medium: A kinetic and mechanistic study. J. Mol. Catalysis A: Chemical. 267: 65-71, 2007.