Structure via PubChem · Public domain (PubChem)
benfotiamine
Sign in to saveBenfotiamine (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 the late 1950s in Japan.
Chemical data
- Formula
- C19H23N4O6PS
- Molecular weight
- 466.4 g/mol
- IUPAC name
- S-[(Z)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate
- SMILES
- CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(/CCOP(=O)(O)O)\SC(=O)C2=CC=CC=C2)/C
- InChIKey
- BTNNPSLJPBRMLZ-LGMDPLHJSA-N
- XLogP
- 0.5
- Polar surface area
- 181 Ų
- H-bond donors
- 3
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Research
268 papers- Benfotiamine and Cognitive Decline in Alzheimer's Disease: Results of a Randomized Placebo-Controlled Phase IIa Clinical Trial.Journal of Alzheimer's disease : JAD · 2020
- Thiamine and benfotiamine: Focus on their therapeutic potential.Heliyon · 2023
- Potential of Benfotiamine in the treatment of neuropsychological disorders.Molecular biology reports · 2025
- Benfotiamine Reduces Dendritic Cell Inflammatory Potency.Endocrine, metabolic & immune disorders drug targets · 2021
- Therapeutic potential of benfotiamine and its molecular targets.European review for medical and pharmacological sciences · 2018
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 466.107592
Show 4 more facts
- chemical formula
- C₁₉H₂₃N₄O₆PS
- canonical SMILES
- CC1=NC=C(C(=N1)N)CN(C=O)C(=C(CCOP(=O)(O)O)SC(=O)C2=CC=CC=C2)C
- Commons category
- Benfotiamine
- isomeric SMILES
- C/C(=C(\CCOP(=O)(O)O)SC(=O)c1ccccc1)N(C=O)Cc1cnc(C)[nH]c1=N
Sources (1)
via Wikidata · CC0
~4 min read
Encyclopedic overview
7 sectionsContents
- Uses
- Adverse effects
- Pharmacology
- Chemistry
- Research
- See also
- References
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449055379 | IUPAC_name = S-[2-{[(4-Amino-2-methylpyrimidin-5-yl)methyl] (formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate | image = Benfotiamine.svg | image_class = skin-invert-image | image2 = Benfotiamine ball-and-stick.png | image_class2 = bg-transparent
| Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = OTC | routes_of_administration = Oral
Excerpted from Wikipedia’s “benfotiamine” article, available under the CC BY-SA 4.0 licence.