Tiagabine (CHEM002298)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:55 UTC
Update Date2016-11-09 01:08:44 UTC
Accession NumberCHEM002298
Identification
Common NameTiagabine
ClassSmall Molecule
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Anticonvulsant
  • Drug
  • GABA Agonist
  • Metabolite
  • Neuroprotective Agent
  • Neurotransmitter Uptake Inhibitor
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
GabitrilKegg
(-)-(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)-isomerHMDB
(R)-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid, hydrochlorideHMDB
N-(4,4-Di(3-methylthien-2-yl)but-3-enyl)nipecotic acidHMDB
Tiagabine hydrochlorideHMDB
Chemical FormulaC20H25NO2S2
Average Molecular Mass375.548 g/mol
Monoisotopic Mass375.133 g/mol
CAS Registry Number115103-54-3
IUPAC Name(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid
Traditional Nametiagabine
SMILESCC1=C(SC=C1)C(=CCCN1CCC[C@H](C1)C(O)=O)C1=C(C)C=CS1
InChI IdentifierInChI=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
Description belongs to the class of organic compounds known as piperidinecarboxylic acids. Piperidinecarboxylic acids 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility2.11e-02 g/L
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 RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9421000000-a3d6cacc1c1eda797cdcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00e9-9141000000-ad3f282e81f21efc67a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004j-1769000000-3559976e948cc2135c8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004j-0984000000-a978c5e709fb0da0cecaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0901000000-f4977b5cba740f9bf146Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0029000000-c5f87e6c22eea721b905Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6s-1298000000-59e359809fb473d67bb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-4190000000-98420f8a2019b820d741Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1009000000-bd93b21b33d14728f6cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-6119000000-718202039949c898877eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5a-9011000000-8572588cb43983c9c799Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-85f99d6f70a9fbf994d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0049000000-db812ecf5f7fb1975926Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9032000000-b4c12faa49251f4425b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-75b21c9b910e4d5d90b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0039000000-b8393c7a9d1fdd48a1a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00r2-5294000000-26284b1d5f7adf9241ffSpectrum
Toxicity Profile
Route of ExposureOral. Tiagabine is nearly completely absorbed (>95%).
Mechanism of ToxicityThough 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.
MetabolismTiagabine is likely metabolized primarily by the 3A isoform subfamily of hepatic cytochrome P450. Route of Elimination: Approximately 2% of an oral dose of tiagabine is excreted unchanged, with 25% and 63% of the remaining dose excreted into the urine and feces, respectively, primarily as metabolites. Half Life: 7-9 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of partial seizures
Minimum Risk LevelNot Available
Health EffectsRespiratory depression was seen in a number of patients, including children, in the context of seizures. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
SymptomsSymptoms most often accompanying tiagabine overdose, alone or in combination with other drugs, have included: seizures including status epilepticus in patients with and without underlying seizure disorders, nonconvulsive status epilepticus, coma, ataxia, confusion, somnolence, drowsiness, impaired speech, agitation, lethargy, myoclonus, spike wave stupor, tremors, disorientation, vomiting, hostility, and temporary paralysis. Respiratory depression was seen in a number of patients, including children, in the context of seizures.
TreatmentThere is no specific antidote for overdose with Tiagabine. If indicated, elimination of unabsorbed drug should be achieved by emesis or gastric lavage; usual precautions should be observed to maintain the airway. General supportive care of the patient is indicated including monitoring of vital signs and observation of clinical status of the patient. Since tiagabine is mostly metabolized by the liver and is highly protein bound, dialysis is unlikely to be beneficial. (2)
Concentrations
Not Available
DrugBank IDDB00906
HMDB IDHMDB0015042
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTiagabine
Chemspider ID54661
ChEBI ID9586
PubChem Compound ID60648
Kegg Compound IDC07503
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Henning Petersen, Peter Nielsen, Michael Cain, Subhash Patel, “Crystalline Tiagabine monohydrate, its preparation and use.” U.S. Patent US5354760, issued April, 1991.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10530690
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22592677
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23770680
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23997364
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24440890
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24500879
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25663257
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=9097364
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=9449883