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MedKoo Cat#: 563151 | Name: Sulbutiamine
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Description:

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

Sulbutiamine is an antioxidant that act by inhibiting oxidative stress induced retinal ganglion cell death.

Chemical Structure

Sulbutiamine
Sulbutiamine
CAS#3286-46-2

Theoretical Analysis

MedKoo Cat#: 563151

Name: Sulbutiamine

CAS#: 3286-46-2

Chemical Formula: C32H46N8O6S2

Exact Mass: 702.2982

Molecular Weight: 702.89

Elemental Analysis: C, 54.68; H, 6.60; N, 15.94; O, 13.66; S, 9.12

Price and Availability

Size Price Availability Quantity
5g USD 250.00
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Related CAS #
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Synonym
Sulbutiamine; Bisibuthiamine; Bisibutiamine; Arcalion; Vitaberin;
IUPAC/Chemical Name
[(Z)-4-[(4-Amino-2-methylpyrimidin-5-yl)methyl-formylamino]-3-[[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-(2-methylpropanoyloxy)pent-2-en-3-yl]disulfanyl]pent-3-enyl] 2-methylpropanoate
InChi Key
CKHJPWQVLKHBIH-ZDSKVHJSSA-N
InChi Code
InChI=1S/C32H46N8O6S2/c1-19(2)31(43)45-11-9-27(21(5)39(17-41)15-25-13-35-23(7)37-29(25)33)47-48-28(10-12-46-32(44)20(3)4)22(6)40(18-42)16-26-14-36-24(8)38-30(26)34/h13-14,17-20H,9-12,15-16H2,1-8H3,(H2,33,35,37)(H2,34,36,38)/b27-21-,28-22-
SMILES Code
CC(C)C(OCC/C(SS/C(CCOC(C(C)C)=O)=C(N(CC1=CN=C(C)N=C1N)C=O)/C)=C(N(CC2=CN=C(C)N=C2N)C=O)\C)=O
Appearance
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
Shelf Life
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 702.89 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: García-Torres I, De la Mora-De la Mora I, Hernández-Alcántara G, Molina-Ortiz D, Caballero-Salazar S, Olivos-García A, Nava G, López-Velázquez G, Enríquez-Flores S. First characterization of a microsporidial triosephosphate isomerase and the biochemical mechanisms of its inactivation to propose a new druggable target. Sci Rep. 2018 Jun 5;8(1):8591. doi: 10.1038/s41598-018-26845-z. PubMed PMID: 29872223; PubMed Central PMCID: PMC5988755. 2: Sevim S, Kaleağası H, Taşdelen B. Sulbutiamine shows promising results in reducing fatigue in patients with multiple sclerosis. Mult Scler Relat Disord. 2017 Aug;16:40-43. doi: 10.1016/j.msard.2017.05.010. Epub 2017 Jun 9. PubMed PMID: 28755683. 3: Farid NF, Abdelwahab NS. Stability-Indicating HPTLC Method for Studying Stress Degradation Behavior of Sulbutiamine HCl. J Chromatogr Sci. 2016 Apr;54(4):609-17. doi: 10.1093/chromsci/bmv226. Epub 2016 Jan 11. PubMed PMID: 26759487; PubMed Central PMCID: PMC4885403. 4: Majid AS, Yin ZQ, Ji D. Sulphur antioxidants inhibit oxidative stress induced retinal ganglion cell death by scavenging reactive oxygen species but influence nuclear factor (erythroid-derived 2)-like 2 signalling pathway differently. Biol Pharm Bull. 2013;36(7):1095-110. PubMed PMID: 23811559. 5: Kwag J, Majid AS, Kang KD. Evidence for neuroprotective effect of sulbutiamine against oxygen-glucose deprivation in rat hippocampal CA1 pyramidal neurons. Biol Pharm Bull. 2011;34(11):1759-64. PubMed PMID: 22040892. 6: Sobolevsky T, Rodchenkov G. Sulbutiamine in sports. Drug Test Anal. 2010 Nov-Dec;2(11-12):643-6. doi: 10.1002/dta.183. Epub 2010 Oct 22. PubMed PMID: 21204296. 7: Kang KD, Majid AS, Kim KA, Kang K, Ahn HR, Nho CW, Jung SH. Sulbutiamine counteracts trophic factor deprivation induced apoptotic cell death in transformed retinal ganglion cells. Neurochem Res. 2010 Nov;35(11):1828-39. doi: 10.1007/s11064-010-0249-5. Epub 2010 Aug 31. PubMed PMID: 20809085. 8: Volvert ML, Seyen S, Piette M, Evrard B, Gangolf M, Plumier JC, Bettendorff L. Benfotiamine, a synthetic S-acyl thiamine derivative, has different mechanisms of action and a different pharmacological profile than lipid-soluble thiamine disulfide derivatives. BMC Pharmacol. 2008 Jun 12;8:10. doi: 10.1186/1471-2210-8-10. PubMed PMID: 18549472; PubMed Central PMCID: PMC2435522. 9: Levin OS, Slizkova IuB. [The use of enerion in the treatment of asthenic disorders in patients after mild cranio-cerebral trauma]. Zh Nevrol Psikhiatr Im S S Korsakova. 2007;107(5):44-8. Russian. PubMed PMID: 18379496. 10: Ollat H, Laurent B, Bakchine S, Michel BF, Touchon J, Dubois B. [Effects of the association of sulbutiamine with an acetylcholinesterase inhibitor in early stage and moderate Alzheimer disease]. Encephale. 2007 Mar-Apr;33(2):211-5. French. PubMed PMID: 17675917. 11: Litvinovich EF, Langeman TI, Litvinovich SF. [The use of sulbuthiamine (enerion) in the combined therapy of patients with symptomatic focal epilepsy]. Zh Nevrol Psikhiatr Im S S Korsakova. 2006;106(12):68-70. Russian. PubMed PMID: 17274400. 12: Douzenis A, Michopoulos I, Lykouras L. Sulbutiamine, an 'innocent' over the counter drug, interferes with therapeutic outcome of bipolar disorder. World J Biol Psychiatry. 2006;7(3):183-5. PubMed PMID: 16861144. 13: Bizot JC, Herpin A, Pothion S, Pirot S, Trovero F, Ollat H. Chronic treatment with sulbutiamine improves memory in an object recognition task and reduces some amnesic effects of dizocilpine in a spatial delayed-non-match-to-sample task. Prog Neuropsychopharmacol Biol Psychiatry. 2005 Jul;29(6):928-35. PubMed PMID: 15951087. 14: Dmitriev DG, Gamidov SI, Permiakova OV. [Clinical efficacy of the drug enerion in the treatment of patients with psychogenic (functional) erectile dysfunction]. Urologiia. 2005 Jan-Feb;(1):32-5. Russian. PubMed PMID: 15776829. 15: Shah SN; Sulbutiamine Study Group. Adjuvant role of vitamin B analogue (sulbutiamine) with anti-infective treatment in infection associated asthenia. J Assoc Physicians India. 2003 Sep;51:891-5. PubMed PMID: 14710977. 16: Van Reeth O. Pharmacologic and therapeutic features of sulbutiamine. Drugs Today (Barc). 1999 Mar;35(3):187-92. PubMed PMID: 12973384. 17: Kiew KK, Wan Mohamad WB, Ridzuan A, Mafauzy M. Effects of sulbutiamine on diabetic polyneuropathy: an open randomised controlled study in type 2 diabetics. Malays J Med Sci. 2002 Jan;9(1):21-7. PubMed PMID: 22969314; PubMed Central PMCID: PMC3436103. 18: Trovero F, Gobbi M, Weil-Fuggaza J, Besson MJ, Brochet D, Pirot S. Evidence for a modulatory effect of sulbutiamine on glutamatergic and dopaminergic cortical transmissions in the rat brain. Neurosci Lett. 2000 Sep 29;292(1):49-53. PubMed PMID: 10996447. 19: Lôo H, Poirier MF, Ollat H, Elatki S. [Effects of sulbutiamine (Arcalion 200) on psycho-behavioral inhibition in major depressive episodes]. Encephale. 2000 Mar-Apr;26(2):70-5. French. PubMed PMID: 10858919. 20: Ahmed MA, Elbeshlawy MM. Potentiometric sensors for the selective determination of sulbutiamine. J Pharm Biomed Anal. 1999 Nov;21(2):415-21. PubMed PMID: 10703998.