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B9636

Sigma-Aldrich

S-Benzoylthiamine O-monophosphate

Synonym(s):

Benfotiamine

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About This Item

Empirical Formula (Hill Notation):
C19H23N4O6PS
CAS Number:
22457-89-2
Molecular Weight:
466.45
EC Number:
245-013-4
MDL number:
MFCD00057343
UNSPSC Code:
12352116
PubChem Substance ID:
24892147
NACRES:
NA.79

Assay

≥98% (TLC)

form

powder or crystals

color

white to off-white

storage temp.

2-8°C

SMILES string

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+

InChI key

BTNNPSLJPBRMLZ-GHRIWEEISA-N

Related Categories

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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David A Fraser et al.
Diabetes care, 35(5), 1095-1097 (2012-03-27)
To study the effects of long-term oral benfotiamine supplementation on peripheral nerve function and soluble inflammatory markers in patients with type 1 diabetes. The study randomly assigned 67 patients with type 1 diabetes to receive 24-month benfotiamine (300 mg/day) or
Alaa Alkhalaf et al.
PloS one, 7(7), e40427-e40427 (2012-07-14)
Formation of advanced glycation endproducts (AGEs), endothelial dysfunction, and low-grade inflammation are intermediate pathways of hyperglycemia-induced vascular complications. We investigated the effect of benfotiamine on markers of these pathways in patients with type 2 diabetes and nephropathy. Patients with type
Lars P Kihm et al.
Journal of the American Society of Nephrology : JASN, 22(5), 914-926 (2011-04-23)
Residual renal function and the integrity of the peritoneal membrane contribute to morbidity and mortality among patients treated with peritoneal dialysis. Glucose and its degradation products likely contribute to the deterioration of the remnant kidney and damage to the peritoneum.
The Effect of Benfothiamin and Vitamin D in Ischemia/Reperfusion Model of Rat Skeletal Muscle
Keskin O
The American Journal of Cardiology, 121(8), e4-e4 (2018)
Benfotiamine, a synthetic S-acyl thiamine derivative, has different mechanisms of action and a different pharmacological profile than lipid-soluble thiamine disulfide derivatives
Volvert M L, et al.
BioMed Central Pharmacology, 8(1), 10-10 (2008)
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