4-aminohex-5-enoic acid

• ChemBase编号: 951
• 分子式: C6H11NO2
• 平均质量: 129.15704
• 单一同位素质量: 129.0789786
• SMILES: OC(=O)CCC(N)C=C
• Canonical SMILES: NC(C=C)CCC(=O)O
• 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

名称和登记号

名称

• IUPAC标准名: 4-aminohex-5-enoic acid
• IUPAC传统名: vigabatrin
• 商标名: 4-Amino-5-hexenoic acid; 4-Aminohexenoic acid; GVG; Sabril (TN); Vigabatrin [USAN:BAN:INN]; Vigabatrina [Spanish]; Vigabatrine; Vigabatrine [French]; Vigabatrinum [Latin]; gamma-Vinyl GABA
• 别名: Vigabatrin; (±)-γ-Vinyl-GABA; (±)-4-Aminohexenoic acid; (R,S)-4-Amino-5-hexenoic acid; (±)-Vigabatrin

登记号

• CAS号: 60643-86-9
• MDL号: MFCD00274577
• PubChem SID: 160964414; 46507052; 24278202
• PubChem CID: 5665

理论计算性质

JChem

• Acid pKa: 4.608113
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -2.1360347
• LogD (pH = 7.4): -2.0948071
• Log P: -2.0949147
• 摩尔折射率: 34.2907 cm^3
• 极化性: 13.588985 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.56
• LOG S: -0.13
• 溶解度: 9.66e+01 g/l

分子性质

理化性质

• 溶解度: 55.1 mg/mL
• 疏水性(logP): 0.1

安全信息

• RTECS编号: MP7745000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

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)

详细说明

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.

参考文献

• 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
• 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
• 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