Tiagabine hydrochloride (CHEM017897)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:43:27 UTC
Update Date2016-11-09 01:15:41 UTC
Accession NumberCHEM017897
Identification
Common NameTiagabine hydrochloride
ClassSmall Molecule
DescriptionA hydrochloride resulting from the reaction of equimolar amounts of tiagabine and hydrogen chloride. A GABA reuptake inhibitor, it is used for the treatment of epilepsy.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acid hydrochlorideChEBI
(-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid hydrochlorideChEBI
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)but-3-en-1-yl]-3-carboxypiperidinium chlorideChEBI
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid monohydrochlorideChEBI
Abbott 70569.hclChEBI
Abbott-70569.1ChEBI
GabitrilChEBI
Tiagabine HCLChEBI
Tiagabine monohydrochlorideChEBI
(-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotate hydrochlorideGenerator
(-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotate hydrochlorideGenerator
(3R)-1-[4,4-Bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylate monohydrochlorideGenerator
N-(4,4-Di(3-methylthien-2-yl)but-3-enyl)nipecotic acidMeSH
Tiagabine, (S)-isomerMeSH
(R)-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid, hydrochlorideMeSH
TiagabineMeSH
Chemical FormulaC20H26ClNO2S2
Average Molecular Mass412.000 g/mol
Monoisotopic Mass411.109 g/mol
CAS Registry Number145821-59-6
IUPAC Name(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid hydrochloride
Traditional Nametiagabine hydrochloride
SMILESCl.[H][C@]1(CCCN(CCC=C(C2=C(C)C=CS2)C2=C(C)C=CS2)C1)C(O)=O
InChI IdentifierInChI=1S/C20H25NO2S2.ClH/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);1H/t16-;/m1./s1
InChI KeyYUKARLAABCGMCN-PKLMIRHRSA-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
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Hydrochloride
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability41.77 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01ot-2940000000-302d6eb683a2a4f80509Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-114887d1f6b53adedb21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-114887d1f6b53adedb21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000900000-114887d1f6b53adedb21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-b9ea9b9dd2300cb33d25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-b9ea9b9dd2300cb33d25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000900000-b9ea9b9dd2300cb33d25Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001255
HMDB IDNot Available
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 IDNot Available
ChEBI ID85388
PubChem Compound ID91274
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available