Tiagabine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Tiagabine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Tiagabine?

The molecule Tiagabine presents a molecular formula of C20H25NO2S2 and its IUPAC name is (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid.

Tiagabine (brand name: Gabitril) is an anticonvulsant medication used to treat partial seizures. It works by decreasing the release of the neurotransmitter GABA..

Tiagabine was approved by the FDA in 1997 and is manufactured by Cephalon, Inc..

The most common side effects of tiagabine are dizziness, headache, nausea, and fatigue..

Tiagabine should not be used by people with kidney or liver disease, or by pregnant or breastfeeding women..

Tiagabine is a prescription medication used to treat partial seizures. It belongs to a class of drugs called anticonvulsants..

Tiagabine is thought to work by decreasing the release of the neurotransmitter GABA..

Tiagabine was approved by the FDA in 1997 and is manufactured by Cephalon, Inc..

The most common side effects of tiagabine are dizziness, headache, nausea, and fatigue..

Tiagabine should not be used by people with kidney or liver disease, or by pregnant or breastfeeding women..

If you have any questions about tiagabine, please talk with your doctor, nurse, pharmacist, or other health care provider..

3D structure

Cartesian coordinates

Geometry of Tiagabine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Tiagabine PBJUNZJWGZTSKL-MRXNPFEDSA-N chemical compound 2D structure molecule svg
Tiagabine

 

Molecule descriptors

 
IUPAC name(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid
InChI codeInChI=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
SMILESCc1ccsc1C(=CCCN1CCC[C@@H](C(=O)O)C1)c1sccc1C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acid
  • (-)-(r)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid
  • (3R)-1-(4,4-BIS(3-METHYL-2-THIENYL)-3-BUTEN-1-YL)-3-PIPERIDINECARBOXYLIC ACID
  • (3R)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid
  • (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid
  • (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid; Gabitril
  • (3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid
  • (R)-(-)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid
  • (R)-1-(4,4-Bis(3-methylthiophen-2-yl)but-3-en-1-yl)piperidine-3-carboxylic acid
  • (R)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-enyl)piperidine-3-carboxylic acid
  • (R)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-enyl)piperidine-3-carboxylic acid hydrochloride
  • (R)-1-[4,4-Bis-(3-methyl-thiophen-2-yl)-but-3-enyl]-piperidine-3-carboxylic acid
  • (R)-1-[4,4-Bis-(3-methyl-thiophen-2-yl)-but-3-enyl]-piperidine-3-carboxylic acid; hydrochloride
  • (R)-Tiagabine
  • (S)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-enyl)piperidine-3-carboxylic acid
  • (r)-n-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]nipecotic acid
  • 1-[4,4-Bis-(3-methyl-4,5-dihydro-thiophen-2-yl)-but-3-enyl]-piperidine-3-carboxylic acid
  • 1-[4,4-Bis-(3-methyl-thiophen-2-yl)-but-3-enyl]-piperidine-3-carboxylic acid; hydrochloride
  • 1006863-69-9
  • 103T543
  • 115103-54-3
  • 3-Piperidinecarboxylic acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-buten-1-yl)-, (3R)-
  • 3-Piperidinecarboxylic acid, 1-(4,4-bis(3-methyl-2-thienyl)-3-butenyl)-, (R)-
  • A-70569-1
  • ABBOTT-70569 FREE BASE
  • ABBOTT-70569-1
  • ABBOTT-705691 FREE BASE
  • ABT-569 FREE BASE
  • AC-7048
  • AMY22648
  • Abbott-70569
  • BDBM50039251
  • BDBM50368628
  • BIDD:GT0018
  • C07503
  • CCG-268358
  • D08588
  • DB00906
  • GTPL4685
  • GTPL4818
  • Gabatril
  • Gabitril
  • HMS3885J16
  • HSDB 7527
  • HY-B0696
  • NCGC00164626-01
  • NNC-050328 FREE BASE
  • NO 050328
  • NO 328
  • NO-050328 FREE BASE
  • NO050328
  • NO050328;NO328;TGB
  • NO328
  • Q907219
  • TGB
  • TGI
  • Tiagabina
  • Tiagabine
  • Tiagabine (INN)
  • Tiagabinum
  • Z80I64HMNP
  • [3H]tiagabine
  • s4675
  • tiagabine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3831531
  • UNII-Z80I64HMNP
  • AKOS016011165
  • BRD-K60160658-003-08-8
  • DTXSID5023663
  • CHEMBL1027
  • CHEBI:9586
  • SCHEMBL34653

Physico-Chemical properties

IUPAC name(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid
Molecular formulaC20H25NO2S2
Molecular weight375.548
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity111.63
LogP5.0
Topological polar surface area97.0

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.