Tiagabine

Tiagabine
Clinical data
Pronunciation	/taɪˈæɡəbiːn/
Trade names	Gabitril
AHFS/Drugs.com	Monograph
MedlinePlus	a698014
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	N03AG06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	90–95%
Protein binding	96%
Metabolism	Hepatic (CYP450 system, primarily CYP3A)
Onset of action	Tmax = 45 min
Elimination half-life	5–8 hours
Excretion	Fecal (63%) and renal (25%)
Identifiers
	IUPAC name (−)-(3R)-1-[4,4-bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidinecarboxylic acid;
CAS Number	115103-54-3 ;
PubChem CID	60648;
IUPHAR/BPS	4685;
DrugBank	DB00906 ;
ChemSpider	54661 ;
UNII	Z80I64HMNP;
KEGG	D08588 ;
ChEBI	CHEBI:9586;
ChEMBL	ChEMBL1027 ;
CompTox Dashboard (EPA)	DTXSID5023663 ;
Chemical and physical data
Formula	C20H25NO2S2
Molar mass	375.55 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@H]1CN(CCC1)CC/C=C(/c2sccc2C)c3sccc3C;
	InChI InChI=1S/C20H25NO2S2/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23)/t16-/m1/s1 ; Key:PBJUNZJWGZTSKL-MRXNPFEDSA-N ;
	(verify)

Tiagabine, sold under the brand name Gabitril, is an anticonvulsant medication produced by Cephalon that is used in the treatment of epilepsy. The drug is also used off-label in the treatment of anxiety disorders including panic disorder.

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c Leduc B (24 January 2012). "Antiseizure Drugs". In Lemke TL, Williams DA (eds.). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 562–. ISBN 978-1-60913-345-0.
^ ^a ^b ^c "Gabitril (tiagabine hydrochloride) Tablets. U.S. Full Prescribing Information" (PDF). Cephalon, Inc. Retrieved 8 April 2016.
^ Brodie MJ (1995). "Tiagabine pharmacology in profile". Epilepsia. 36 (Suppl 6): S7 – S9. doi:10.1111/j.1528-1157.1995.tb06015.x. PMID 8595791. S2CID 27336198.