TGI

Tiagabine

Created:2021-10-20
Last modified:  2022-06-08

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Chemical Details

Formal Charge0
Atom Count50
Chiral Atom Count1
Bond Count52
Aromatic Bond Count10
2D diagram of TGI

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Chemical Component Summary

NameTiagabine
Synonyms(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid; Gabitril
Systematic Name (OpenEye OEToolkits)(3~{R})-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid
FormulaC20 H25 N O2 S2
Molecular Weight375.548
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs12.01Cc1ccsc1C(=C\CCN1CCCC(C1)C(=O)O)\c1sccc1C
SMILESCACTVS3.385Cc1ccsc1C(=CCCN2CCC[CH](C2)C(O)=O)c3sccc3C
SMILESOpenEye OEToolkits2.0.7Cc1ccsc1C(=CCCN2CCCC(C2)C(=O)O)c3c(ccs3)C
Canonical SMILESCACTVS3.385 Cc1ccsc1C(=CCCN2CCC[C@H](C2)C(O)=O)c3sccc3C
Canonical SMILESOpenEye OEToolkits2.0.7 Cc1ccsc1C(=CCCN2CCC[C@H](C2)C(=O)O)c3c(ccs3)C
InChIInChI1.03 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
InChIKeyInChI1.03 PBJUNZJWGZTSKL-MRXNPFEDSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB00906 
NameTiagabine
Groups
  • approved
  • investigational
DescriptionTiagabine is an anti-convulsive medication. It is also used in the treatment for panic disorder as are a few other anticonvulsants. Though the exact mechanism by which tiagabine exerts its effect on the human body is unknown, it does appear to operate as a selective GABA reuptake inhibitor.
Synonyms
  • Tiagabinum
  • Tiagabina
  • Tiagabine hydrochloride
  • Tiagabine
Brand Names
  • Gabitril
  • Tiagabine Hydrochloride
IndicationFor the treatment of partial seizures
Categories
  • Anti-epileptic Agent
  • Anticonvulsants
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Cytochrome P-450 CYP3A Substrates
ATC-CodeN03AG06
CAS number115103-54-3

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Sodium- and chloride-dependent GABA transporter 1MATNGSKVADGQISTEVSEAPVANDKPKTLVVKVQKKAADLPDRDTWKGR...unknowninhibitor
UDP-glucuronosyltransferase 1A1MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...unknownsubstrate
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1027
PubChem 40467242, 60648
ChEMBL CHEMBL1027
ChEBI CHEBI:9586