Tiagabine
Title: Tiagabine
CAS Registry Number: 115103-54-3
CAS Name: (3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid
Additional Names: (-)-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid; TGB
Manufacturers' Codes: NO-328; NO-05-0328; NNC-05-0328; A-70569
Molecular Formula: C20H25NO2S2
Molecular Weight: 375.55
Percent Composition: C 63.96%, H 6.71%, N 3.73%, O 8.52%, S 17.08%
Literature References: GABA uptake inhibitor. Prepn: F. C. Groenvald, C. Braestrup, WO 8700171 (1987 to Novo); F. C. Gronvald, C. Braestrup, US 5010090 (1991 to Novo Nordisk); K. E. Andersen et al., J. Med. Chem. 36, 1716 (1993). Pharmacology: C. L. Faingold et al., Exp. Neurol. 126, 225 (1994). HPLC determn in human plasma: L. E. Gustavson, S. Chu, J. Chromatogr. 574, 313 (1992). Clinical evaluation as add-on therapy: J. Bauer et al., J. Epilepsy 8, 83 (1995). Review of pharmacology: W. J. Giardina, ibid. 7, 161-166 (1994); and chemistry: H. Mengel, Epilepsia 35, Suppl. 5, S81-S84 (1994). Review of clinical experience: J. P. Leach, M. J. Brodie, Lancet 351, 203 (1998).
 
Derivative Type: Hydrochloride
CAS Registry Number: 145821-59-6
Trademarks: Gabitril (Novo Nordisk)
Molecular Formula: C20H25NO2S2.HCl
Molecular Weight: 412.01
Percent Composition: C 58.30%, H 6.36%, N 3.40%, O 7.77%, S 15.57%, Cl 8.60%
Properties: White to off-white, odorless crystalline powder, mp 192° (dec) (Mengel). [a]D20 -11°. pKa1 3.3; pKa2 9.4. Partition coefficient (octanol/water): 39.3 (pH 7.4). Soly in water: 3%. Practically insol in hexane.
Melting point: mp 192° (dec) (Mengel)
pKa: pKa1 3.3; pKa2 9.4
Optical Rotation: [a]D20 -11°
Log P: Partition coefficient (octanol/water): 39.3 (pH 7.4)
 
Therap-Cat: Anticonvulsant.
Keywords: Anticonvulsant.

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