Benfotiamine

Benfotiamine
Clinical data
Trade names	Milgamma
Other names	S-Benzoylthiamine O-monophosphate
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	A11DA03 (WHO) ;
Legal status
Legal status	In general: Over-the-counter (OTC);
Identifiers
	IUPAC name S-[2-{[(4-Amino-2-methylpyrimidin-5-yl)methyl] (formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate;
CAS Number	22457-89-2 ;
PubChem CID	3032771;
ChemSpider	2297665 ;
UNII	Y92OUS2H9B;
ChEBI	CHEBI:41039 ;
ChEMBL	ChEMBL1491875 ;
CompTox Dashboard (EPA)	DTXSID3045433 ;
ECHA InfoCard	100.040.906
Chemical and physical data
Formula	C19H23N4O6PS
Molar mass	466.45 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=P(O)(O)OCCC(/SC(=O)c1ccccc1)=C(/N(C=O)Cc2cnc(nc2N)C)C;
	InChI 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- ; Key:BTNNPSLJPBRMLZ-LGMDPLHJSA-N ;
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Benfotiamine (rINN, or S-benzoylthiamine O-monophosphate) is a synthetic, fat-soluble, S-acyl derivative of thiamine (vitamin B1) that is approved in some countries as a medication or dietary supplement to treat diabetic sensorimotor polyneuropathy. Benfotiamine was developed in late 1950s in Japan.^[1]^[2]

^ Wada T, Takagi H, Minakami H, Hamanaka W, Okamoto K, Ito A, Sahashi Y (July 1961). "A new thiamine derivative, S-benzoylthiamine O-monophosphate". Science. 134 (3473): 195–196. Bibcode:1961Sci...134..195W. doi:10.1126/science.134.3473.195. PMID 13782394. S2CID 10384617.
^ Sambon M, Wins P, Bettendorff L (May 2021). "Neuroprotective Effects of Thiamine and Precursors with Higher Bioavailability: Focus on Benfotiamine and Dibenzoylthiamine". International Journal of Molecular Sciences. 22 (11): 5418. doi:10.3390/ijms22115418. PMC 8196556. PMID 34063830.

[1] Wada T, Takagi H, Minakami H, Hamanaka W, Okamoto K, Ito A, Sahashi Y (July 1961). "A new thiamine derivative, S-benzoylthiamine O-monophosphate". Science. 134 (3473): 195–196. Bibcode:1961Sci...134..195W. doi:10.1126/science.134.3473.195. PMID 13782394. S2CID 10384617.

[2] Sambon M, Wins P, Bettendorff L (May 2021). "Neuroprotective Effects of Thiamine and Precursors with Higher Bioavailability: Focus on Benfotiamine and Dibenzoylthiamine". International Journal of Molecular Sciences. 22 (11): 5418. doi:10.3390/ijms22115418. PMC 8196556. PMID 34063830.

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