4-aminohex-5-enoic acid

• ChemBase ID: 951
• Molecular Formular: C6H11NO2
• Molecular Mass: 129.15704
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-aminohex-5-enoic acid
• IUPAC Traditional name: vigabatrin
• Brand Name: 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
• Synonyms: Vigabatrin; (±)-γ-Vinyl-GABA; (±)-4-Aminohexenoic acid; (R,S)-4-Amino-5-hexenoic acid; (±)-Vigabatrin

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.608113
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.1360347
• LogD (pH = 7.4): -2.0948071
• Log P: -2.0949147
• Molar Refractivity: 34.2907 cm^3
• Polarizability: 13.588985 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.56
• LOG S: -0.13
• Solubility (Water): 9.66e+01 g/l

PROPERTIES

Physical Property

• Solubility: 55.1 mg/mL
• Hydrophobicity(logP): 0.1

Safety Information

• RTECS: MP7745000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

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

DETAILS

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.

REFERENCES

• 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