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B9636

Sigma-Aldrich

S-Benzoylthiamine O-monophosphate

Synonyme(s) :

Benfotiamine

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About This Item

Formule empirique (notation de Hill):
C19H23N4O6PS
Numéro CAS:
22457-89-2
Poids moléculaire :
466.45
Numéro CE :
245-013-4
Numéro MDL:
MFCD00057343
Code UNSPSC :
12352116
ID de substance PubChem :
24892147
Nomenclature NACRES :
NA.79

Pureté

≥98% (TLC)

Forme

powder or crystals

Couleur

white to off-white

Température de stockage

2-8°C

Chaîne SMILES 

Cc1ncc(CN(C=O)\C(C)=C(/CCOP(O)(O)=O)SC(=O)c2ccccc2)c(N)n1

InChI

1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)/b17-13+

Clé InChI

BTNNPSLJPBRMLZ-GHRIWEEISA-N

Description générale

S-Benzoylthiamine O-monophosphate (Benfotiamine) is an amphiphilic S-acyl thiamine derivative. It is a lipid-soluble vitamin. Benfotiamine contains a thiazole ring. Benfotiamine has a greater bioavailability than thiamine.

Application

S-Benzoylthiamine O-monophosphate has been used to determine its effect on ischemia and reperfusion in skeletal muscles of rat.

Actions biochimiques/physiologiques

S-Benzoylthiamine O-monophosphate (Benfotiamine) is a therapeutic agent. It helps in the prevention of diabetic complications such as, retinopathy, neuropathy and nephropathy. Benfotiamine inhibits the synthesis of glycation end products (AGEs) in diabetes. Benfotiamine is considered as a nutraceutical product for the prevention of diabetic neuropathy.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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The multifaceted therapeutic potential of benfotiamine
Balakumar P, et al.
Pharmacological Research, 61(6), 482-488 (2010)
Guilherme Vannucchi Portari et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 48(4-5), 799-802 (2013-02-02)
Thiamine and benfotiamine are vitamin B1 and pro-vitamin B1 substances, respectively. Vitamin B1 plays an essential role in energy metabolism, and its deficiency leads to neurologic and cardiovascular pathologies, as seen in alcoholics. This study presents new data about the
Alaa Alkhalaf et al.
Diabetes care, 33(7), 1598-1601 (2010-04-24)
To investigate the effect of benfotiamine on urinary albumin excretion (UAE) and the tubular damage marker kidney injury molecule-1 (KIM-1) in patients with type 2 diabetes and nephropathy. Patients with type 2 diabetes and UAE equivalent to 15-300 mg/24 h
Rajesh Katare et al.
Journal of molecular and cellular cardiology, 49(4), 625-638 (2010-06-15)
Benfotiamine (BFT) is a transketolase activator that directs glucose to the pentose phosphate pathway. The present study investigated whether BFT improves the recovery after myocardial infarction (MI) and explored underlying mechanisms of protection. Non-diabetic and streptozotocin-induced type 1 diabetic mice
Pitchai Balakumar et al.
Pharmacological research, 61(6), 482-488 (2010-03-02)
Thiamine, known as vitamin B(1), plays an essential role in energy metabolism. Benfotiamine (S-benzoylthiamine O-monophoshate) is a synthetic S-acyl derivative of thiamine. Once absorbed, benfotiamine is dephosphorylated by ecto-alkaline phosphatase to lipid-soluble S-benzoylthiamine. Transketolase is an enzyme that directs the
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