CAS 60643-86-9|CAS 68506-86-5|Vigabatrinum [Latin]|vigabatrin|4-Amino-5-hexenoic acid|Vigabatrina [Spanish]|Sabril (TN)|gamma-Vinyl GABA|4-Aminohexenoic acid|Vigabatrine|Vigabatrin [USAN:BAN:INN]|4-...

基本信息

化学结构

分子式

C₆H₁₁NO₂

分子量

129.15704

精确质量

129.0789786

电荷

InChI

InChI=1S/C6H11NO2/c1-2-5(7)3-4-6(8)9/h2,5H,1,3-4,7H2,(H,8,9)

InChIKey

PJDFLNIOAUIZSL-UHFFFAOYSA-N

Canonic Smiles

NC(C=C)CCC(=O)O

Isomeric Smiles

OC(=O)CCC(N)C=C

计算属性

JChem

LogD (pH = 7.4)

-2.09

LogD (pH = 5.5)

-2.14

Log P

-2.09

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

4.61

极化表面积

63.32

极化性

13.68

摩尔折射率

34.29

LOG S

-0.07

数据来源

名称和标识

商标名

Vigabatrinum [Latin]4-Amino-5-hexenoic acidVigabatrina [Spanish]Sabril (TN)gamma-Vinyl GABA4-Aminohexenoic acidVigabatrineVigabatrin [USAN:BAN:INN]Vigabatrine [French]GVG

IUPAC传统名

vigabatrin

IUPAC标准名

4-aminohex-5-enoic acid

别名

Vigabatrin(±)-γ-Vinyl-GABA(±)-Vigabatrin(±)-4-Aminohexenoic acid(R,S)-4-Amino-5-hexenoic acidgamma-vinyl GABA4-Amino-5-hexenoic acidGVGvigabatringamma-vinyl-gamma-aminobutyric acidgamma-Vinyl GABA

API名称

Vigabatrin

国际非专利药品(INN)

vigabatrinevigabatrinavigabatrinvigabatrinum

名称和标识

数据登录号

PubChem SID

4650705216096441424278202135610142

CAS号

PubChem CID

MDL号

DrugBank ID

BRENDA Ligand数据库

2350931402131682947329860

维基百科标题

Vigabatrin

BindingDB数据库

50118886

PubMed文献链接

2206117822234618213617402092632320018576208783402206118222061177

MetaboLights数据库

MTBLS1693MTBLS3725MTBLS2145MTBLS2406MTBLS1411MTBLS1642MTBLS1071

BKMS React数据库

2350931402986029473213168

SureChEMBL数据库

SCHEMBL26714

BRENDA数据库

2.6.1.195.4.3.82.6.1.962.6.1.2

CompTox数据库

UniProt数据库

EnzymePortal数据库

ACToR数据库

专利号

LINCS数据库

CHEBI ID

CHEBI:9979CHEBI:63638

CHEMBL

CHEMBL89598

Drug Central Database

2,819

KEGG DRUG Database

D00535

KEGG ID

C07500

数据登录号

化合物性质

理化性质

疏水性(logP)

0.1

溶解度

55.1 mg/mL

药理学性质

相关基因信息

human ... GABBR1(2550), GABBR2(9568), GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)

安全信息

安全公开号

26-36

Warning

MP7745000

刺激性 (Xi)

H315-H319-H335

急性毒性（口服，皮肤接触，吸入），类别4

皮肤刺激，类别2

眼刺激，类别2

皮肤过敏，类别1

特定目标器官毒性 -一次接触，类别3

dust mask type N95 (US), Eyeshields, Gloves

P261-P305+P351+P338

36/37/38

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB01080

Drug Groups

approved

Description

An analogue of gamma-aminobutyric acid. It is an irreversible inhibitor of 4-aminobutyrate transaminase, the enzyme responsible for the catabolism of gamma-aminobutyric acid. (From Martindale The Extra Pharmacopoeia, 31st ed)

Indication

For use as an adjunctive treatment (with other drugs) in treatment resistant epilepsy, complex partial seizures, secondary generalized seizures, and for monotherapy use in infantile spasms in West syndrome.

Pharmacology

Vigabatrin, is an anticonvulsant chemically unrelated to other anticonvulsants. Vigabatrin inhibits the catabolism of GABA. It is an analog of GABA, but it is not a receptor agonist. Vigabatrin irreversibly inhibits the enzyme GABA transaminase.

Affected Organisms

Humans and other mammals

Biotransformation

Almost no metabolic transformation. Does not induce the hepatic cytochrome P450 system.

Absorption

Rapidly absorbed following oral administration. Food may slightly decrease the rate, but not the extent, of absorption.

Half Life

5-8 hours in young adults, 12-13 hours in elderly.

Protein Binding

Little to none

Elimination

Vigabatrin is not significantly metabolized; it is eliminated primarily through renal excretion.

Distribution

* 1.1 L/kg

Clearance

* 2.4 +/- 0.8 L/h [Infant]
* 5.7 +/- 2.5 L/h [Children]

References

• Gram L, Larsson OM, Johnsen A, Schousboe A: Experimental studies of the influence of vigabatrin on the GABA system. Br J Clin Pharmacol. 1989;27 Suppl 1:13S-17S. [Pubmed]

• Browne TR: Pharmacokinetics of antiepileptic drugs. Neurology. 1998 Nov;51(5 Suppl 4):S2-7. [Pubmed]

• Lindberger M, Luhr O, Johannessen SI, Larsson S, Tomson T: Serum concentrations and effects of gabapentin and vigabatrin: observations from a dose titration study. Ther Drug Monit. 2003 Aug;25(4):457-62. [Pubmed]

• Zwanzger P, Baghai TC, Schuele C, Strohle A, Padberg F, Kathmann N, Schwarz M, Moller HJ, Rupprecht R: Vigabatrin decreases cholecystokinin-tetrapeptide (CCK-4) induced panic in healthy volunteers. Neuropsychopharmacology. 2001 Nov;25(5):699-703. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

Sigma Aldrich

V8261

Biochem/physiol Actions
Irreversible GABA transaminase inhibitor. Increases intracellular concentration of GABA in nerve endings; possesses antiepileptic activity.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. V8261.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

ChEBI

CHEBI:63638

A gamma-amino acid having a gamma-vinyl GABA structure. It is an irreversible inhibitor of gamma-aminobutyric 664 acid transaminase

描述信息

参考文献

PubChem文献

数据源提供

• Browne TR: Pharmacokinetics of antiepileptic drugs. Neurology. 1998 Nov;51(5 Suppl 4):S2-7. Pubmed

• Gram L, Larsson OM, Johnsen A, Schousboe A: Experimental studies of the influence of vigabatrin on the GABA system. Br J Clin Pharmacol. 1989;27 Suppl 1:13S-17S. Pubmed

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

商标名

Vigabatrinum [Latin]4-Amino-5-hexenoic acidVigabatrina [Spanish]Sabril (TN)gamma-Vinyl GABA4-Aminohexenoic acidVigabatrineVigabatrin [USAN:BAN:INN]Vigabatrine [French]GVG

IUPAC传统名

vigabatrin

IUPAC标准名

4-aminohex-5-enoic acid

别名

API名称

Vigabatrin

国际非专利药品(INN)

vigabatrinevigabatrinavigabatrinvigabatrinum

数据登录号

PubChem SID

4650705216096441424278202135610142

CAS号

PubChem CID

MDL号

DrugBank ID

BRENDA Ligand数据库

2350931402131682947329860

维基百科标题

Vigabatrin

BindingDB数据库

50118886

PubMed文献链接

2206117822234618213617402092632320018576208783402206118222061177

MetaboLights数据库

MTBLS1693MTBLS3725MTBLS2145MTBLS2406MTBLS1411MTBLS1642MTBLS1071

BKMS React数据库

2350931402986029473213168

SureChEMBL数据库

SCHEMBL26714

BRENDA数据库

2.6.1.195.4.3.82.6.1.962.6.1.2

CompTox数据库

UniProt数据库

EnzymePortal数据库

ACToR数据库

专利号

LINCS数据库

CHEBI ID

CHEBI:9979CHEBI:63638

CHEMBL

CHEMBL89598

Drug Central Database

KEGG DRUG Database

KEGG ID

描述信息

DB01080

Drug Groups

approved

Description

Indication

Pharmacology

Affected Organisms

Humans and other mammals

Biotransformation

Almost no metabolic transformation. Does not induce the hepatic cytochrome P450 system.

Absorption

Rapidly absorbed following oral administration. Food may slightly decrease the rate, but not the extent, of absorption.

Half Life

5-8 hours in young adults, 12-13 hours in elderly.

Protein Binding

Little to none

Elimination

Vigabatrin is not significantly metabolized; it is eliminated primarily through renal excretion.

Distribution

* 1.1 L/kg

Clearance

* 2.4 +/- 0.8 L/h [Infant]
* 5.7 +/- 2.5 L/h [Children]

References

• Gram L, Larsson OM, Johnsen A, Schousboe A: Experimental studies of the influence of vigabatrin on the GABA system. Br J Clin Pharmacol. 1989;27 Suppl 1:13S-17S. [Pubmed]

• Browne TR: Pharmacokinetics of antiepileptic drugs. Neurology. 1998 Nov;51(5 Suppl 4):S2-7. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

Sigma Aldrich

V8261

ChEBI

CHEBI:63638

A gamma-amino acid having a gamma-vinyl GABA structure. It is an irreversible inhibitor of gamma-aminobutyric 664 acid transaminase

参考文献

PubChem文献

数据源提供

• Browne TR: Pharmacokinetics of antiepileptic drugs. Neurology. 1998 Nov;51(5 Suppl 4):S2-7. Pubmed

• Gram L, Larsson OM, Johnsen A, Schousboe A: Experimental studies of the influence of vigabatrin on the GABA system. Br J Clin Pharmacol. 1989;27 Suppl 1:13S-17S. Pubmed

生物活性

PubChem BioAssay

化合物性质

理化性质

疏水性(logP)

0.1

溶解度

55.1 mg/mL

药理学性质

化合物信息

ID:951