Vigabatrin
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MedKoo CAT#: 318979

CAS#: 60643-86-9

Description: 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.


Price and Availability

Size Price Shipping out time Quantity
1g USD 2650 2 Weeks
2g USD 3950 2 Weeks
5g USD 5950 2 Weeks
10g USD 7950 2 Weeks
20g USD 11450 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-04-09. Prices are subject to change without notice.

Vigabatrin is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 318979
Name: Vigabatrin
CAS#: 60643-86-9
Chemical Formula: C6H11NO2
Exact Mass: 129.07898
Molecular Weight: 129.159
Elemental Analysis: C, 55.80; H, 8.58; N, 10.84; O, 24.77


Synonym: CPP109, CPP-109, CPP 109, RMI 71754, RMI71754, RMI-71754, MDL 71754, MDL-71754, MDL71754, Vigabatrin, gamma-vinyl-GABA, Sabril, Sabrilex

IUPAC/Chemical Name: 4-aminohex-5-enoic acid

InChi Key: PJDFLNIOAUIZSL-UHFFFAOYSA-N

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

SMILES Code: C=CC(N)CCC(O)=O


Technical Data

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Nøhr MK, Frølund S, Holm R, Nielsen CU. Pharmacokinetic aspects of the anti-epileptic drug substance vigabatrin: focus on transporter interactions. Ther Deliv. 2014 Aug;5(8):927-42. doi: 10.4155/tde.14.55. Review. PubMed PMID: 25337649.

2: Hemming K, Maguire MJ, Hutton JL, Marson AG. Vigabatrin for refractory partial epilepsy. Cochrane Database Syst Rev. 2013 Jan 31;1:CD007302. doi: 10.1002/14651858.CD007302.pub2. Review. PubMed PMID: 23440814.

3: Fecarotta C, Sergott RC. Vigabatrin-associated visual field loss. Int Ophthalmol Clin. 2012 Summer;52(3):87-94, xii. doi: 10.1097/IIO.0b013e31825a10a6. Review. PubMed PMID: 22668542.

4: Heim MK, Gidal BE. Vigabatrin-associated retinal damage: potential biochemical mechanisms. Acta Neurol Scand. 2012 Oct;126(4):219-28. doi: 10.1111/j.1600-0404.2012.01684.x. Epub 2012 May 26. Review. PubMed PMID: 22632110.

5: Gaily E. Vigabatrin monotherapy for infantile spasms. Expert Rev Neurother. 2012 Mar;12(3):275-86. doi: 10.1586/ern.12.3. Review. PubMed PMID: 22364326.

6: Xiao Y, Gan L, Wang J, Luo M, Luo H. Vigabatrin versus carbamazepine monotherapy for epilepsy. Cochrane Database Syst Rev. 2012 Jan 18;1:CD008781. doi: 10.1002/14651858.CD008781.pub2. Review. PubMed PMID: 22258989.

7: Pellock JM. Balancing clinical benefits of vigabatrin with its associated risk of vision loss. Acta Neurol Scand Suppl. 2011;(192):83-91. doi: 10.1111/j.1600-0404.2011.01603.x. Review. PubMed PMID: 22061183.

8: Walker SD, Kälviäinen R. Non-vision adverse events with vigabatrin therapy. Acta Neurol Scand Suppl. 2011;(192):72-82. doi: 10.1111/j.1600-0404.2011.01602.x. Review. PubMed PMID: 22061182.

9: Plant GT, Sergott RC. Understanding and interpreting vision safety issues with vigabatrin therapy. Acta Neurol Scand Suppl. 2011;(192):57-71. doi: 10.1111/j.1600-0404.2011.01601.x. Review. PubMed PMID: 22061181.

10: Sergott RC, Westall CA. Primer on visual field testing, electroretinography, and other visual assessments for patients treated with vigabatrin. Acta Neurol Scand Suppl. 2011;(192):48-56. doi: 10.1111/j.1600-0404.2011.01600.x. Review. PubMed PMID: 22061180.

11: Carmant L. Vigabatrin therapy for infantile spasms: review of major trials in Europe, Canada, and the United States; and recommendations for dosing. Acta Neurol Scand Suppl. 2011;(192):36-47. doi: 10.1111/j.1600-0404.2011.01599.x. Review. PubMed PMID: 22061179.

12: Faught E. Vigabatrin therapy for refractory complex partial seizures: review of clinical trial experience in the United States. Acta Neurol Scand Suppl. 2011;(192):29-35. doi: 10.1111/j.1600-0404.2011.01598.x. Review. PubMed PMID: 22061178.

13: Ben-Menachem E, Sander JW. Vigabatrin therapy for refractory complex partial seizures: review of major European trials. Acta Neurol Scand Suppl. 2011;(192):16-28. doi: 10.1111/j.1600-0404.2011.01597.x. Review. PubMed PMID: 22061177.

14: Ben-Menachem E. Mechanism of action of vigabatrin: correcting misperceptions. Acta Neurol Scand Suppl. 2011;(192):5-15. doi: 10.1111/j.1600-0404.2011.01596.x. Review. PubMed PMID: 22061176.

15: Pesaturo KA, Spooner LM, Belliveau P. Vigabatrin for infantile spasms. Pharmacotherapy. 2011 Mar;31(3):298-311. doi: 10.1592/phco.31.3.298. Review. PubMed PMID: 21361740.

16: Maguire MJ, Hemming K, Wild JM, Hutton JL, Marson AG. Prevalence of visual field loss following exposure to vigabatrin therapy: a systematic review. Epilepsia. 2010 Dec;51(12):2423-31. doi: 10.1111/j.1528-1167.2010.02772.x. Epub 2010 Nov 10. Review. PubMed PMID: 21070215.

17: Sergott RC. Recommendations for visual evaluations of patients treated with vigabatrin. Curr Opin Ophthalmol. 2010 Nov;21(6):442-6. doi: 10.1097/ICU.0b013e32833f0085. Review. PubMed PMID: 20811279.

18: Bentué-Ferrer D, Tribut O, Verdier MC; le groupe Suivi Thérapeutique Pharmacologique de la Société Française de Pharmacologie et de Thérapeutique. [Therapeutic drug monitoring of vigabatrin]. Therapie. 2010 Jan-Feb;65(1):23-7. doi: 10.2515/therapie/2009067. Epub 2010 Mar 8. Review. French. PubMed PMID: 20205991.

19: Tolman JA, Faulkner MA. Vigabatrin: a comprehensive review of drug properties including clinical updates following recent FDA approval. Expert Opin Pharmacother. 2009 Dec;10(18):3077-89. doi: 10.1517/14656560903451690. Review. PubMed PMID: 19954276.

20: Willmore LJ, Abelson MB, Ben-Menachem E, Pellock JM, Shields WD. Vigabatrin: 2008 update. Epilepsia. 2009 Feb;50(2):163-73. Review. PubMed PMID: 19230067.