(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid

• ChemBase ID: 782
• Molecular Formular: C20H25NO2S2
• Molecular Mass: 375.548
• Monoisotopic Mass: 375.13267105
• SMILES: s1c(/C(=C\CCN2C[C@@H](CCC2)C(=O)O)/c2sccc2C)c(cc1)C
• Canonical SMILES: OC(=O)[C@@H]1CCCN(C1)CC/C=C(\c1sccc1C)/c1sccc1C
• InChI: 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
• InChIKey: PBJUNZJWGZTSKL-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid
• IUPAC Traditional name: tiagabine
• Brand Name: Gabitril
• Synonyms: Tiagabina [INN-Spanish]; Tiagabinum [INN-Latin]; Tiagabine

Database IDs

• CAS Number: 115103-54-3
• PubChem SID: 160964245; 46505560
• PubChem CID: 60648

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.1433096
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.5883915
• LogD (pH = 7.4): 2.59872
• Log P: 2.6014485
• Molar Refractivity: 115.3171 cm^3
• Polarizability: 40.297897 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.98
• LOG S: -4.25
• Solubility (Water): 2.11e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.6

DETAILS

DrugBank - DB00906

• Drug Groups: approved
• Description: Tiagabine 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.
• Indication: For the treatment of partial seizures
• Pharmacology: Tiagabine is used primarily as an anticonvulsant for the adjunctive treatment of epilepsy. The precise mechanism by which Tiagabine exerts its antiseizure effect is unknown, although it is believed to be related to its ability to enhance the activity of gamma aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. Tiagabine binds to recognition sites associated with the GABA uptake carrier. It is thought that, by this action, Tiagabine blocks GABA uptake into presynaptic neurons, permitting more GABA to be available for receptor binding on the surfaces of post-synaptic cells.
• Toxicity: mptoms 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Tiagabine is likely metabolized primarily by the 3A isoform subfamily of hepatic cytochrome P450.
• Absorption: Tiagabine is nearly completely absorbed (>95%).
• Half Life: 7-9 hours
• Protein Binding: 96%
• 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.
• Clearance: * 109 mL/min [Healthy subjects]
• External Links: Wikipedia; RxList; Drugs.com