Vigabatrin
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    WARNING: This product is for research use only, not for human or veterinary use.

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

1g
USD 2650
10g
USD 7950
Size
Price

2g
USD 3950
20g
USD 11450
Size
Price

5g
USD 5950

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).

Harmonized System Code:
2934.99.90.01


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.