Benfotiamine


Benfotiamine

drugbox
IUPAC_name = S- [("Z")-2- [(4-amino-2-methylpyrimidin-5-yl)methyl-
formylamino] -5-phosphonooxypent-2-en-3-yl] benzenecarbothioate



CAS_number = 22457-89-2
ATC_prefix = A11
ATC_suffix = DA03
PubChem = 3032771
C = 19 | H = 23 | N = 4 | O = 6 | P = 1 | S = 1
molecular_weight = 466.449 g/mol
synonyms = "S"-benzoylthiamine O-monophosphate
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Benfotiamine (rINN, or S-benzoylthiamine O-monophoshate) is a synthetic S-acyl derivative of thiamine (vitamine B1). After absorption, benfotiamine can be dephosphorylated by cells bearing an ecto-alkaline phosphatase to the lipid-soluble S-benzoylthiamine. [ Yamazaki M (1968), Studies on the absorption of S-benzoylthiamine O-monophosphate : (I) Metabolism in tissue homogenates. Vitamins 38 (1) 12–20. ] Benfotiamine should not be confused with allithiamine, a naturally occurring thiamine disulfide derivative with a distinct pharmacological profile. [ M.L. Volvert, S. Seyen, M. Piette, B. Evrard, M. Gangolf, J.C. Plumier and L. Bettendorff (2008) Benfotiamine, a synthetic S-acyl thiamine derivative, has different mechanisms of action and a different pharmacological profile than lipid-soluble thiamine disulfide derivatives. BMC Pharmacology 8: 10. http://dx.doi.org/10.1186/1471-2210-8-10]

Uses

The primary use of this antioxidant is as an "anti-AGE" supplement. [ [http://www.life-enhancement.com/article_template.asp?id=1925 Reducing Glycation Reactions for Better Health and Longer Life] ] In a trial, benfotiamine lowered AGE by 40%.cite journal
journal=Diabetes|date=2000 May |volume=49 (Suppl1)|issue= A143 | ppages=583
title=Benfotiamine Inhibits Intracellular Formation of Advanced Glycation End Products in vivo
author=J Lin, A Alt, J Liersch, RG Bretzel, M Brownlee| accessdate=2008-02-08
] However, in Germany doctors have been known to combine benfotiamine with pyridoxine hydrochloride and use it to treat patients with nerve damage and nerve pain such as sciatica.

At high doses, benfotiamine was shown to be effective for the treatment of diabetic retinopathy, neuropathy, and nephropathy. It is thought that treatment with benfotiamine leads to increased intracellular thiamine diphosphate levels, a cofactor of transketolase. This enzyme directs advanced glycation and lipoxidation end products (AGE's, ALE's) substrates to the pentose phosphate pathway, thus reducing tissue AGEs. [ Since AGEs are the actual agents productive of diabetic complications, in theory, if diabetic patients could block the action of AGEs completely by benfotiamine, strict blood sugar control, with its disruption of lifestyle and risks to health and life by severe hypoglycemic episodes, could be avoided, with revolutionary implications for the treatment of diabetes. Hammes HP, Du X, Edelstein D, Taguchi T, Matsumura T, Ju Q, Lin J, Bierhaus A, Nawroth P, Hannak D, Neumaier M, Bergfeld R, Giardino I, Brownlee M (2003) Benfotiamine blocks three major pathways of hyperglycemic damage and prevents experimental diabetic retinopathy. Nat Med 9(3):294-299] cite journal |author=Stirban A, Negrean M, Stratmann B, "et al" |title=Adiponectin decreases postprandially following a heat-processed meal in individuals with type 2 diabetes: an effect prevented by benfotiamine and cooking method |journal=Diabetes Care |volume=30 |issue=10 |pages=2514–6 |year=2007 |pmid=17630265 |doi=10.2337/dc07-0302] cite journal |author=Stracke H, Hammes HP, Werkmann D, "et al" |title=Efficacy of benfotiamine versus thiamine on function and glycation products of peripheral nerves in diabetic rats |journal=Exp. Clin. Endocrinol. Diabetes |volume=109 |issue=6 |pages=330–6 |year=2001 |pmid=11571671 |doi=10.1055/s-2001-17399] cite journal |author=Stirban A, Negrean M, Stratmann B, "et al" |title=Benfotiamine prevents macro- and microvascular endothelial dysfunction and oxidative stress following a meal rich in advanced glycation end products in individuals with type 2 diabetes |journal=Diabetes Care |volume=29 |issue=9 |pages=2064–71 |year=2006 |pmid=16936154 |doi=10.2337/dc06-0531] cite journal |author=Babaei-Jadidi R, Karachalias N, Ahmed N, Battah S, Thornalley PJ |title=Prevention of incipient diabetic nephropathy by high-dose thiamine and benfotiamine |journal=Diabetes |volume=52 |issue=8 |pages=2110–20 |year=2003 |pmid=12882930 |doi=]

References

External links

* [http://news.bbc.co.uk/1/hi/health/2761469.stm BBC news story: Back pain drug 'may aid diabetics']


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