B9636
S-Benzoylthiamine O-monophosphate
Synonym(s):
Benfotiamine
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About This Item
Empirical Formula (Hill Notation):
C19H23N4O6PS
CAS Number:
Molecular Weight:
466.45
NACRES:
NA.79
PubChem Substance ID:
UNSPSC Code:
12352116
EC Number:
245-013-4
MDL number:
InChI key
BTNNPSLJPBRMLZ-GHRIWEEISA-N
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+
SMILES string
Cc1ncc(CN(C=O)\C(C)=C(/CCOP(O)(O)=O)SC(=O)c2ccccc2)c(N)n1
assay
≥98% (TLC)
form
powder or crystals
color
white to off-white
storage temp.
2-8°C
Quality Level
Related Categories
Application
S-Benzoylthiamine O-monophosphate has been used to determine its effect on ischemia and reperfusion in skeletal muscles of rat.
Biochem/physiol Actions
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.
General description
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.
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
Umesh C S Yadav et al.
Free radical biology & medicine, 48(10), 1423-1434 (2010-03-12)
This study was designed to investigate the molecular mechanisms by which benfotiamine, a lipid-soluble analogue of vitamin B1, affects lipopolysaccharide (LPS)-induced inflammatory signals leading to cytotoxicity in the mouse macrophage cell line RAW264.7. Benfotiamine prevented LPS-induced apoptosis, expression of the
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
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
Sonia Tarallo et al.
Acta diabetologica, 49 Suppl 1, S141-S151 (2012-04-25)
Pericytes regulate vascular tone, perfusion pressure and endothelial cell (EC) proliferation in capillaries. Thiamine and benfotiamine counteract high glucose-induced damage in vascular cells. We standardized two human retinal pericyte (HRP)/EC co-culture models to mimic the diabetic retinal microvascular environment. We
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