Benfotiamine - Wikipedia https://en.wikipedia.

org/wiki/Benfotiamine

Benfotiamine
Benfotiamine (rINN, or S-benzoylthiamine
O-monophosphate) is a synthetic, fat-soluble, Benfotiamine
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]

Contents
Uses
Adverse effects
Pharmacology
Chemistry
Research Clinical data
References Trade names Milgamma
Other names S-Benzoylthiamine O-monophosphate

Uses AHFS/Drugs.com International Drug Names (http

s://www.drugs.com/international
Benfotiamine is primarily marketed as an over- /benfotiamine.html)
the-counter drug to treat diabetic Routes of Oral
[3]
polyneuropathy. A 2021 review described two administration
clinical trials and concluded that more research ATC code A11DA03 (WHO (https://www.w
is needed.[4] hocc.no/atc_ddd_index/?code=
A11DA03))
As of 2017, benfotiamine was marketed as a
pharmaceutical drug in many countries under Legal status
the following brand names: Benalgis, Legal status In general: Over-the-counter
Benfogamma, Benforce, Benfotiamina,
(OTC)
Biotamin, Biotowa, Milgamma, and Vilotram.[5]
It was also marketed in some jurisdictions as a Identifiers
combination drug with cyanocobalamin as IUPAC name
Milgamma, in combination with pyridoxine as
S-[2-{[(4-Amino-2-methylpyrimidin-5-yl)methyl] (formy
Milgamma, in combination with metformin as
l)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzen
Benforce-M, and with thiamine as Vitafos.[5]
ecarbothioate

Adverse effects

1 of 4 6/03/2022, 3:06 am
Benfotiamine - Wikipedia https://en.wikipedia.org/wiki/Benfotiamine

There is little published data on adverse effects. CAS Number 22457-89-2 (https://commonche
In one study of a combination of benfotiamine, mistry.cas.org/detail?cas_rn=22
pyridoxine, and cyanocobalamin, around 8% of
457-89-2)
people taking the drug experienced nausea,
dizziness, stomach ache and weight gain.[6] PubChem CID 3032771 (https://pubchem.ncbi.
nlm.nih.gov/compound/303277
Pharmacology 1)
ChemSpider 2297665 (https://www.chemspid
Benfotiamine is dephosphorylated to er.com/Chemical-Structure.2297
S-benzoylthiamine by ecto-alkaline 665.html)
phosphatases present in the intestinal mucosa,
UNII Y92OUS2H9B (https://precision.
and is then hydrolyzed to thiamine by
thioesterases in the liver.[7] Benfotiamine is fda.gov/uniisearch/srs/unii/Y92
more bioavailable than thiamine salts,[8] OUS2H9B)
providing higher levels of thiamine in muscle, ChEBI CHEBI:41039 (https://www.ebi.a
brain, liver, and kidney.[6]
c.uk/chebi/searchId.do?chebiId
Benfotiamine mainly acts on peripheral tissues =CHEBI:41039)
through an increase in transketolase activity. ChEMBL ChEMBL1491875 (https://www.
[7][6][9]
ebi.ac.uk/chembldb/index.php/c
ompound/inspect/ChEMBL1491
Chemistry 875)
CompTox DTXSID3045433 (https://compt
Benfotiamine is a lipid derivative of thiamine, Dashboard (EPA)
ox.epa.gov/dashboard/chemical
specifically a synthetic S-acyl Vitamin B1
/details/DTXSID3045433)
analogue; its chemical name is
S-benzoylthiamine O-monophosphate. [10] It has ECHA InfoCard 100.040.906 (https://echa.europ
very low solubility in water or other aqueous a.eu/substance-information/-/su
solvents.[7] bstanceinfo/100.040.906)
Chemical and physical data
Research Formula C19H23N4O6PS
Molar mass 466.45 g·mol−1
Benfotiamine has been studied in laboratory
models of diabetic retinopathy, neuropathy, and 3D model Interactive image (https://chema
(JSmol)
nephropathy.[10] A 2021 review described two pps.stolaf.edu/jmol/jmol.php?mo
clinical trials and concluded that more research del=O%3DP%28O%29%28O%
is needed.[4] 29OCCC%28%2FSC%28%3D
O%29c1ccccc1%29%3DC%2
Administration of benfotiamine may increase
8%2FN%28C%3DO%29Cc2cn
intracellular levels of thiamine diphosphate, a
c%28nc2N%29C%29C)
cofactor of transketolase,[10] and based on
metabolic theories of Alzheimer's disease, it has SMILES
been studied in preclinical models of Alzheimer's O=P(O)(O)OCCC(/SC(=O)c1ccccc1)=C(/N(C=O)Cc2c
disease.[11] nc(nc2N)C)C
InChI
References 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

2 of 4 6/03/2022, 3:06 am
Benfotiamine - Wikipedia https://en.wikipedia.org/wiki/Benfotiamine

1. Wada, T; Takagi, H; Minakami, H; (25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H

Hamanaka, W; Okamoto, K; Ito, A; Sahashi, 3,(H2,20,21,22)(H2,26,27,28)/b17-13-
Y (21 July 1961). "A New Thiamine Key:BTNNPSLJPBRMLZ-LGMDPLHJSA-N
Derivative, S-Benzoylthiamine (what is this?) (verify)
O-Monophosphate". Science. 134 (3473):
195–96. Bibcode:1961Sci...134..195W (http
s://ui.adsabs.harvard.edu/abs/1961Sci...134..
195W). doi:10.1126/science.134.3473.195 (h
ttps://doi.org/10.1126%2Fscience.134.3473.1
95). PMID 13782394 (https://pubmed.ncbi.nl
m.nih.gov/13782394). S2CID 10384617 (http
s://api.semanticscholar.org/CorpusID:103846
17).
2. Sambon, Margaux; Wins, Pierre; Bettendorff,
Lucien (2021-05-21). "Neuroprotective
Effects of Thiamine and Precursors with
Higher Bioavailability: Focus on Benfotiamine
and Dibenzoylthiamine" (https://www.ncbi.nl
m.nih.gov/pmc/articles/PMC8196556).
International Journal of Molecular Sciences.
22 (11): 5418. doi:10.3390/ijms22115418 (htt
ps://doi.org/10.3390%2Fijms22115418).
ISSN 1422-0067 (https://www.worldcat.org/is
sn/1422-0067). PMC 8196556 (https://www.n
cbi.nlm.nih.gov/pmc/articles/PMC8196556).
PMID 34063830 (https://pubmed.ncbi.nlm.ni
h.gov/34063830).
3. McCarty, MF; Inoguchi, T (2008). "11.
Targeting Oxidant Stress as a Strategy for
Preventing Vascular Complications of
Diabetes and Metabolic Syndrome" (https://b
ooks.google.com/books?id=9FvCD-a32VMC
&pg=PA213). In Pasupuleti, Vijai K.;
Anderson, James W. (eds.). Nutraceuticals,
glycemic health and type 2 diabetes
(1st ed.). Ames, Iowa: Wiley-Blackwell/IFT
Press. p. 213. ISBN 9780813804286.
4. Zaheer A, Zaheer F, Saeed H, Tahir Z, Tahir
MW (April 2021). "A Review of Alternative
Treatment Options in Diabetic
Polyneuropathy" (https://www.ncbi.nlm.nih.go
v/pmc/articles/PMC8139599). Cureus. 13 (4):
e14600. doi:10.7759/cureus.14600 (https://d
oi.org/10.7759%2Fcureus.14600).
PMC 8139599 (https://www.ncbi.nlm.nih.gov/
pmc/articles/PMC8139599). PMID 34040901
(https://pubmed.ncbi.nlm.nih.gov/34040901).
5. "Benfotiamine International brands" (https://w
ww.drugs.com/international/benfotiamine.htm
l). Drugs.com. Retrieved 14 March 2017.

3 of 4 6/03/2022, 3:06 am
Benfotiamine - Wikipedia https://en.wikipedia.org/wiki/Benfotiamine

6. Panel on Food Additives and Nutrient Sources added to Food (2008). "Scientific Opinion:
Benfotiamine, thiamine monophosphate chloride and thiamine pyrophosphate chloride, as
sources of vitamin B1 added for nutritional purposes to food supplements" (http://www.efsa.eur
opa.eu/sites/default/files/scientific_output/files/main_documents/864.pdf) (PDF). The EFSA
Journal. 864: 1–31.
7. Patel, SM; Patel, RP; Prajapati, BG (2012). Patel, S (ed.). "Solubility enhancement of
benfotiamine, a lipid derivative of thiamine by solid dispersion technique" (https://www.ncbi.nlm.
nih.gov/pmc/articles/PMC3467834). Journal of Pharmacy & Bioallied Sciences. US National
Library of Medicine and National Institutes of Health: J Pharm Bioallied Sci. 4 (Suppl 1): S104–
S105. doi:10.4103/0975-7406.94157 (https://doi.org/10.4103%2F0975-7406.94157).
PMC 3467834 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3467834). PMID 23066179 (http
s://pubmed.ncbi.nlm.nih.gov/23066179).
8. Bitsch, R; Wolf, M; Moeller, J; Heuzeroth, L; Grueneklee, D (1991). "Bioavailability Assessment
of the Lipophilic Benfotiamine as Compared to a Water-Soluble Thiamin Derivative". Ann Nutr
Metab. 35 (5): 292–96. doi:10.1159/000177659 (https://doi.org/10.1159%2F000177659).
PMID 1776825 (https://pubmed.ncbi.nlm.nih.gov/1776825).
9. Yamazaki, M (1968). "Studies on the absorption of S-benzoylthiamine O-monophosphate : (I)
Metabolism in tissue homogenates". Vitamins. 38 (1): 12–20.
10. Balakumar P, Rohilla A, Krishan P, Solairaj P, Thangathirupathi A (June 2010). "The
multifaceted therapeutic potential of benfotiamine". Pharmacol Res. 61 (6): 482–88.
doi:10.1016/j.phrs.2010.02.008 (https://doi.org/10.1016%2Fj.phrs.2010.02.008).
PMID 20188835 (https://pubmed.ncbi.nlm.nih.gov/20188835).
11. Gibson, GE; Hirsch, JA; Cirio, RT; Jordan, BD; Fonzetti, P; Elder, J (July 2013). "Abnormal
thiamine-dependent processes in Alzheimer's Disease. Lessons from diabetes" (https://www.nc
bi.nlm.nih.gov/pmc/articles/PMC3609887). Molecular and Cellular Neurosciences. 55: 17–25.
doi:10.1016/j.mcn.2012.09.001 (https://doi.org/10.1016%2Fj.mcn.2012.09.001). PMC 3609887
(https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3609887). PMID 22982063 (https://pubmed.nc
bi.nlm.nih.gov/22982063).

Retrieved from "https://en.wikipedia.org/w/index.php?title=Benfotiamine&oldid=1070035211"

This page was last edited on 5 February 2022, at 09:34 (UTC).

Text is available under the Creative Commons Attribution-ShareAlike License 3.0; additional terms may apply. By
using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the
Wikimedia Foundation, Inc., a non-profit organization.

4 of 4 6/03/2022, 3:06 am