Tiagabine

Tiagabine
Clinical data
Pronunciation/tˈæɡəbn/
Trade namesGabitril
AHFS/Drugs.comMonograph
MedlinePlusa698014
Pregnancy
category
  • AU: B3
Routes of
administration
Oral (tablets)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability90–95%[2]
Protein binding96%[2]
MetabolismHepatic (CYP450 system,[2] primarily CYP3A)[3]
Onset of actionTmax = 45 min[3]
Elimination half-life5–8 hours[4]
ExcretionFecal (63%) and renal (25%)[3]
Identifiers
  • (−)-(3R)-1-[4,4-bis(3-methyl-2-thienyl)-3-buten-1-yl]-3-piperidinecarboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H25NO2S2
Molar mass375.55 g·mol−1
3D model (JSmol)
  • O=C(O)[C@H]1CN(CCC1)CC/C=C(/c2sccc2C)c3sccc3C
  • 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 checkY
  • Key:PBJUNZJWGZTSKL-MRXNPFEDSA-N checkY
  (verify)

Tiagabine (trade 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 and panic disorder.

  1. ^ 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.
  2. ^ 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.
  3. ^ a b c "Gabitril (tiagabine hydrochloride) Tablets. U.S. Full Prescribing Information" (PDF). Cephalon, Inc. Retrieved 8 April 2016.
  4. ^ 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.