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- Title
Crystal Structures of a New Polymorphic Form of Gabapentin Monohydrate and the E and Z Isomers of 4-Tertiarybutylgabapentin.
- Authors
Vasudev, Prema G.; Aravinda, Subrayashastry; Ananda, Kuppanna; Veena, Shettykere Dayananda; Nagarajan, Kuppuswamy; Shamala, Narayanaswamy; Balaram, Padmanabhan
- Abstract
Gabapentin, a widely used antiepileptic drug, crystallizes in multiple polymorphic forms. A new crystal form of gabapentin monohydrate in the space group Pbca is reported and the packing arrangement compared with that of a previously reported polymorph in the space group P21/c [Ibers, J.A. (2001) Acta Crystallogr; C57:641]. Gabapentin polymorphs can also occur from a selection of one of the two distinct chair forms of the 1,1-disubstituted cyclohexane. Crystal structures of the E and Z isomers of 4- tert-butylgabapentin provide models for analyzing anticipated packing modes in the conformational isomers of gabapentin. The E isomer crystallized in the space group Pca21, while the Z isomer crystallized in the space group P21/c. The crystal structure of E-4- tert-butylgabapentin provides the only example of a structure in a non-centrosymmetric space group. Crystal structures of the hydrochloride and hydrobromide salts of 4- tert-butyl derivatives are reported. The results suggest that for gabapentin, a large ‘polymorph-space’ may be anticipated, in view of the multiple conformational states that are accessible to the molecule.
- Subjects
NUCLEAR isomers; CYCLOHEXANE; ANTICONVULSANTS; GENETIC polymorphisms; MOLECULES; SPACE groups
- Publication
Chemical Biology & Drug Design, 2009, Vol 73, Issue 1, p83
- ISSN
1747-0277
- Publication type
Article
- DOI
10.1111/j.1747-0285.2008.00726.x