9417. Tiagabine

Nomenclature

CAS number: 115103-54-3
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidinecarboxylic acid; ()-(R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid; TGB; NO-328; NO-05-0328; NNC-05-0328; A-70569.
C20H25NO2S2; mol wt 375.55.
C 63.96%, H 6.71%, N 3.73%, O 8.52%, S 17.08%.

Description and references

Selective GABA reuptake inhibitor. Prepn: F. C. Groenvald, C. Braestrup, WO 8700171 (1987 to Novo); eidem, US 5010090 (1991 to Novo Nordisk); K. E. Andersen et al., J. Med. Chem. 36, 1716 (1993). HPLC determn in human plasma: L. E. Gustavson, S. Chu, J. Chromatogr. 574, 313 (1992). 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 in epilepsy: J. P. Leach, M. J. Brodie, Lancet 351, 203-207 (1998); of pharmacology and therapeutic potential in anxiety disorders: T. L. Schwartz, N. Nihalani, Expert Opin. Pharmacother. 7, 1977-1987 (2006).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 145821-59-6
Gabitril (Cephalon).
C20H25NO2S2.HCl; mol wt 412.01.
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). [α]D20 11°. pKa1 3.3; pKa2 9.4. Partition coefficient (octanol/water): 39.3 (pH 7.4). Soly in water: 3%. Sol in aqueous base. Practically insol in hexane; insol in heptane.

Therapeutic Category

Anticonvulsant.

Keywords

Anticonvulsant