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115103-54-3 molecular structure
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(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 and InChIs

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

Cite this record

CBID:782 http://www.chembase.cn/molecule-782.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
115103-54-3
PubChem SID
160964245
46505560
PubChem CID
60648

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00906 external link
PubChem 60648 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.1433096  H Acceptors
H Donor LogD (pH = 5.5) 2.5883915 
LogD (pH = 7.4) 2.59872  Log P 2.6014485 
Molar Refractivity 115.3171 cm3 Polarizability 40.297897 Å3
Polar Surface Area 40.54 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.98  LOG S -4.25 
Solubility (Water) 2.11e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
2.6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00906 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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