Vigabatrin

• CAT Number: I010029
• CAS Number: 60643-86-9
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Purity: ≥95%
• Target: GABA transaminase inhibitor
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4 °C for short term, or -20 °C for long term
• IUPAC Name: 4-aminohex-5-enoic acid
• 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
• SMILES: C=CC(CCC(=O)O)N

Vigabatrin, also known as gamma-vinyl-GABA, is an antiepileptic drug that inhibits the breakdown of γ-aminobutyric acid (GABA) by acting as a suicide inhibitor of GABA transaminase (GABA-T). It is a structural analog of GABA, but does not bind to GABA receptors. Vigabatrin is an irreversible suicide inhibitor of gamma-aminobutyric acid transaminase (GABA-T), the enzyme responsible for the catabolism of GABA, which increases the level of GABA in the brain. Vigabatrin is a racemic compound, and its [S]-enantiomer is pharmacologically active.

Reference

1:Evaluation of inner retinal layers with optic coherence tomography in vigabatrin-exposed patients. Tuğcu B, Bitnel MK, Kaya FS, Güveli BT, Ataklı D.Neurol Sci. 2017 May 16. doi: 10.1007/s10072-017-2971-0. [Epub ahead of print] PMID: 28508989 2:Hormonal therapy with vigabatrin is superior to hormonal therapy alone in infantile spasms. Knupp KG.J Pediatr. 2017 May;184:235-238. doi: 10.1016/j.jpeds.2017.02.051. No abstract available. PMID: 28434569 3:Reduction of retinal nerve fiber layer thickness in vigabatrin-exposed patients: A meta-analysis. Peng Y, Zhao Y, Hu W, Hu Y, He Y, Zhou Y.Clin Neurol Neurosurg. 2017 Jun;157:70-75. doi: 10.1016/j.clineuro.2017.04.004. Epub 2017 Apr 7. PMID: 28412542 4:Risk of vigabatrin-associated brain abnormalities on MRI in the treatment of infantile spasms is dose-dependent. Hussain SA, Tsao J, Li M, Schwarz MD, Zhou R, Wu JY, Salamon N, Sankar R.Epilepsia. 2017 Apr;58(4):674-682. doi: 10.1111/epi.13712. Epub 2017 Feb 23. PMID: 28230253 5:The Vigabatrin Induced Retinal Toxicity is Associated with Photopic Exposure and Taurine Deficiency: An In Vivo Study. Tao Y, Yang J, Ma Z, Yan Z, Liu C, Ma J, Wang Y, Yang Z, Huang YF.Cell Physiol Biochem. 2016;40(5):831-846. Epub 2016 Dec 7. PMID: 27941319 Free Article6:Neuroimaging Abnormalities in a Child With Infantile Spasms on High-Dose Vigabatrin. Sun LR, Bosemani T, Smith-Hicks CL.Pediatr Neurol. 2017 Feb;67:109-110. doi: 10.1016/j.pediatrneurol.2016.10.004. Epub 2016 Oct 13. No abstract available. PMID: 27908655 7:Determination of enantiomeric vigabatrin by derivatization with diacetyl-l-tartaric anhydride followed by ultra-high performance liquid chromatography-quadrupole-time-of-flight mass spectrometry. Zhao J, Shin Y, Jin Y, Jeong KM, Lee J.J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Jan 1;1040:199-207. doi: 10.1016/j.jchromb.2016.11.016. Epub 2016 Nov 10. PMID: 27866846 8:Aberrant mTOR signaling and disrupted autophagy: The missing link in potential vigabatrin-associated ocular toxicity? Vogel KR, Ainslie GR, Pearl PL, Gibson KM.Clin Pharmacol Ther. 2017 Apr;101(4):458-461. doi: 10.1002/cpt.581. Epub 2017 Feb 7. PMID: 27864823 9:Safety and effectiveness of hormonal treatment versus hormonal treatment with vigabatrin for infantile spasms (ICISS): a randomised, multicentre, open-label trial. O/’Callaghan FJ, Edwards SW, Alber FD, Hancock E, Johnson AL, Kennedy CR, Likeman M, Lux AL, Mackay M, Mallick AA, Newton RW, Nolan M, Pressler R, Rating D, Schmitt B, Verity CM, Osborne JP; participating investigators..Lancet Neurol. 2017 Jan;16(1):33-42. doi: 10.1016/S1474-4422(16)30294-0. Epub 2016 Nov 10. PMID: 27838190 10:mTOR Inhibition Mitigates Molecular and Biochemical Alterations of Vigabatrin-Induced Visual Field Toxicity in Mice. Vogel KR, Ainslie GR, Schmidt MA, Wisor JP, Gibson KM.Pediatr Neurol. 2017 Jan;66:44-52.e1. doi: 10.1016/j.pediatrneurol.2016.09.016. Epub 2016 Oct 3. PMID: 27816307