Benfotiamine
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| Systematic (IUPAC) name |
| S-[(2Z)-2-{[(4-amino-2-methylpyrimidin-5-yl)methyl] (formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate |
| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| Pregnancy cat. |
? |
| Legal status |
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| Identifiers |
| CAS number |
22457-89-2  Y |
| ATC code |
A11DA03 |
| PubChem |
CID 3032771 |
| ChemSpider |
2297665 Y |
| UNII |
Y92OUS2H9B Y |
| Synonyms |
S-benzoylthiamine O-monophosphate |
| Chemical data |
| Formula |
C19H23N4O6PS |
| Mol. mass |
466.448 g/mol |
| SMILES |
eMolecules & PubChem |
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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- Y
Key:BTNNPSLJPBRMLZ-LGMDPLHJSA-N Y
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Benfotiamine (rINN, or S-benzoylthiamine O-monophosphate) is a synthetic S-acyl derivative of thiamine (vitamin B1). After absorption, benfotiamine can be dephosphorylated by cells bearing an ecto-alkaline phosphatase to the lipid-soluble S-benzoylthiamine.[1] Benfotiamine should not be confused with allithiamine, a naturally occurring thiamine disulfide derivative with a distinct pharmacological profile.[2]
The primary use of this antioxidant is as an "anti-AGE" supplement.[3] In a trial, benfotiamine lowered AGE by 40%.[4] 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,[5] 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.[6][7][8][9][10]
[edit] See also
[edit] References
- ^ Yamazaki M (1968), Studies on the absorption of S-benzoylthiamine O-monophosphate : (I) Metabolism in tissue homogenates. Vitamins 38 (1) 12–20.
- ^ 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
- ^ Reducing Glycation Reactions for Better Health and Longer Life
- ^ J Lin, A Alt, J Liersch, RG Bretzel, M Brownlee (2000 May). "Benfotiamine Inhibits Intracellular Formation of Advanced Glycation End Products in vivo". Diabetes 49 (Suppl1) (A143): 583.
- ^ Balakumar P, Rohilla A, Krishan P, Solairaj P, Thangathirupathi A (2010). "The multifaceted therapeutic potential of benfotiamine". Pharmacol Res 61 (6): 482–8. doi:10.1016/j.phrs.2010.02.008. PMID 20188835.
- ^ 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
- ^ Stirban A, Negrean M, Stratmann B, et al. (2007). "Adiponectin decreases postprandially following a heat-processed meal in individuals with type 2 diabetes: an effect prevented by benfotiamine and cooking method". Diabetes Care 30 (10): 2514–6. doi:10.2337/dc07-0302. PMID 17630265.
- ^ Stracke H, Hammes HP, Werkmann D, et al. (2001). "Efficacy of benfotiamine versus thiamine on function and glycation products of peripheral nerves in diabetic rats". Exp. Clin. Endocrinol. Diabetes 109 (6): 330–6. doi:10.1055/s-2001-17399. PMID 11571671.
- ^ Stirban A, Negrean M, Stratmann B, et al. (2006). "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". Diabetes Care 29 (9): 2064–71. doi:10.2337/dc06-0531. PMID 16936154.
- ^ Babaei-Jadidi R, Karachalias N, Ahmed N, Battah S, Thornalley PJ (2003). "Prevention of incipient diabetic nephropathy by high-dose thiamine and benfotiamine". Diabetes 52 (8): 2110–20. doi:10.2337/diabetes.52.8.2110. PMID 12882930.
[edit] External links
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| Fat soluble |
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D2 ( Ergosterol, Ergocalciferol#) · D3 ( 7-Dehydrocholesterol, Previtamin D3, Cholecalciferol, 25-hydroxycholecalciferol, Calcitriol (1,25-dihydroxycholecalciferol), Calcitroic acid) · D4 ( Dihydroergocalciferol) · D5 · D analogues ( Alfacalcidol, Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol)
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| Water soluble |
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B1 ( Thiamine#) · B2 ( Riboflavin#) · B3 ( Niacin, Nicotinamide#) · B5 ( Pantothenic acid, Dexpanthenol, Pantethine) · B6 ( Pyridoxine#, Pyridoxal phosphate, Pyridoxamine) · B7 ( Biotin) · B9 ( Folic acid, Dihydrofolic acid, Folinic acid) · B12 ( Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide) · Choline
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