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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:13:50 UTC
HMDB IDHMDB0015042
Secondary Accession Numbers
  • HMDB15042
Metabolite Identification
Common NameTiagabine
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.
Structure
Thumb
Synonyms
ValueSource
(-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acidChEBI
(-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acidChEBI
(R)-(-)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acidChEBI
(R)-TiagabineChEBI
TiagabinaChEBI
TiagabinumChEBI
(-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotateGenerator
(-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotateGenerator
(R)-(-)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotateGenerator
Tiagabine, (S)-isomerMeSH
(R)-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid, hydrochlorideMeSH
GabitrilMeSH
N-(4,4-Di(3-methylthien-2-yl)but-3-enyl)nipecotic acidMeSH
Chemical FormulaC20H25NO2S2
Average Molecular Weight375.548
Monoisotopic Molecular Weight375.132670429
IUPAC Name(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid
Traditional Nametiagabine
CAS Registry Number115103-54-3
SMILES
CC1=C(SC=C1)C(=CCCN1CCC[C@H](C1)C(O)=O)C1=C(C)C=CS1
InChI Identifier
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
InChI KeyPBJUNZJWGZTSKL-MRXNPFEDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as piperidinecarboxylic acids. These are compounds containing a piperidine ring which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPiperidinecarboxylic acids and derivatives
Direct ParentPiperidinecarboxylic acids
Alternative Parents
Substituents
  • Piperidinecarboxylic acid
  • Thiophene
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary amine
  • Amino acid
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.021 g/LNot Available
LogP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP4.98ALOGPS
logP2.6ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)9.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity115.32 m³·mol⁻¹ChemAxon
Polarizability41.7 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9421000000-a3d6cacc1c1eda797cdcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9141000000-ad3f282e81f21efc67a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004j-1769000000-3559976e948cc2135c8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0029000000-c5f87e6c22eea721b905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6s-1298000000-59e359809fb473d67bb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-4190000000-98420f8a2019b820d741View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1009000000-bd93b21b33d14728f6cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6119000000-718202039949c898877eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5a-9011000000-8572588cb43983c9c799View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00906 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00906 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00906
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54661
KEGG Compound IDC07503
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTiagabine
METLIN IDNot Available
PubChem Compound60648
PDB IDNot Available
ChEBI ID9586
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Terminates the action of GABA by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A1
Uniprot ID:
P30531
Molecular weight:
67073.0
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Pollack MH, Roy-Byrne PP, Van Ameringen M, Snyder H, Brown C, Ondrasik J, Rickels K: The selective GABA reuptake inhibitor tiagabine for the treatment of generalized anxiety disorder: results of a placebo-controlled study. J Clin Psychiatry. 2005 Nov;66(11):1401-8. [PubMed:16420077 ]
  3. Sheehan DV, Sheehan KH, Raj BA, Janavs J: An open-label study of tiagabine in panic disorder. Psychopharmacol Bull. 2007;40(3):32-40. [PubMed:18007567 ]
  4. Foster AC, Kemp JA: Glutamate- and GABA-based CNS therapeutics. Curr Opin Pharmacol. 2006 Feb;6(1):7-17. Epub 2005 Dec 22. [PubMed:16377242 ]
  5. Sunol C, Babot Z, Cristofol R, Sonnewald U, Waagepetersen HS, Schousboe A: A possible role of the non-GAT1 GABA transporters in transfer of GABA from GABAergic to glutamatergic neurons in mouse cerebellar neuronal cultures. Neurochem Res. 2010 Sep;35(9):1384-90. doi: 10.1007/s11064-010-0196-1. Epub 2010 May 30. [PubMed:20512624 ]
  6. Henjum S, Hassel B: High-affinity GABA uptake and GABA-metabolizing enzymes in pig forebrain white matter: a quantitative study. Neurochem Int. 2007 Jan;50(2):365-70. Epub 2006 Oct 27. [PubMed:17069932 ]