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]
Benfotiamine is primarily marketed as an over-the-counter drug to treat diabetic polyneuropathy.[3] A 2021 review described two clinical trials with positive results for diabetic polyneuropathy and concluded that more research is needed.[4]
As of 2017, benfotiamine was marketed as a pharmaceutical drug in many countries under the following brand names: Benalgis, Benfogamma, Benforce, Benfotiamina, Biotamin, Biotowa, Milgamma, and Vilotram.[5] It was also marketed in some jurisdictions as a combination drug with cyanocobalamin as Milgamma, in combination with pyridoxine as Milgamma, in combination with metformin as Benforce-M, and with thiamine as Vitafos.[5]
Adverse effects
There is little published data on adverse effects. In one study of a combination of benfotiamine, pyridoxine, and cyanocobalamin, around 8% of people taking the drug experienced nausea, dizziness, stomach ache and weight gain.[6]
Pharmacology
Benfotiamine is dephosphorylated to S-benzoylthiamine by ecto-alkaline phosphatases present in the intestinal mucosa, and is then hydrolyzed to thiamine by thioesterases in the liver.[7] Benfotiamine is more bioavailable than thiamine salts,[8] providing higher levels of thiamine in muscle, brain, liver, and kidney.[6]
Benfotiamine mainly acts on peripheral tissues through an increase in transketolase activity.[7][6][9]
Chemistry
Benfotiamine is a lipid derivative of thiamine, specifically a synthetic S-acyl Vitamin B1 analogue; its chemical name is S-benzoylthiamine O-monophosphate.[10] It has very low solubility in water or other aqueous solvents.[7]
Research
Benfotiamine has been studied in laboratory models of diabetic retinopathy, neuropathy, and nephropathy.[10] A 2021 review of its use for diabetic polyneuropathy described two clinical trials which showed improvements in neuropathic pain and neuropathic symptoms scores, the latter of which showed a dose-response effect.[4] The authors concluded that it could potentially serve as an economical supplement to enhance neuropathy treatment and that more research is needed.
Administration of benfotiamine may increase intracellular levels of thiamine diphosphate, a cofactor of transketolase.[10] Based on metabolic theories of Alzheimer's disease, since thiamine-dependent processes are critical in glucose metabolism and are diminished in brains of Alzheimer's disease patients at autopsy, and since treatment of mouse models of Alzheimer's disease with benfotiamine diminishes plaques, decreases phosphorylation of tau and reverses memory deficits, benfotiamine administration has been proposed as a possible intervention to reverse biological and clinical processes of Alzheimer's disease.[11]
^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. PMC8196556. PMID 34063830.
^McCarty MF, Inoguchi T (2008). "11. Targeting Oxidant Stress as a Strategy for Preventing Vascular Complications of Diabetes and Metabolic Syndrome". In Pasupuleti VK, Anderson JW (eds.). Nutraceuticals, glycemic health and type 2 diabetes (1st ed.). Ames, Iowa: Wiley-Blackwell/IFT Press. p. 213. ISBN9780813804286.
^ abZaheer A, Zaheer F, Saeed H, Tahir Z, Tahir MW (April 2021). "A Review of Alternative Treatment Options in Diabetic Polyneuropathy". Cureus. 13 (4): e14600. doi:10.7759/cureus.14600. PMC8139599. PMID 34040901.
^ ab"Benfotiamine International brands". Drugs.com. Retrieved 14 March 2017.
^ abcPanel 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" (PDF). The EFSA Journal. 864: 1–31.
^ abcPatel SM, Patel RP, Prajapati BG (March 2012). Patel S (ed.). "Solubility enhancement of benfotiamine, a lipid derivative of thiamine by solid dispersion technique". Journal of Pharmacy & Bioallied Sciences. J Pharm Bioallied Sci. 4 (Suppl 1): S104–S105. doi:10.4103/0975-7406.94157. PMC3467834. PMID 23066179.
^Bitsch R, Wolf M, Möller J, Heuzeroth L, Grüneklee D (1991). "Bioavailability assessment of the lipophilic benfotiamine as compared to a water-soluble thiamin derivative". Annals of Nutrition & Metabolism. 35 (5): 292–296. doi:10.1159/000177659. PMID 1776825.
^Yamazaki M (1968). "Studies on the absorption of S-benzoylthiamine O-monophosphate : (I) Metabolism in tissue homogenates". Vitamins. 38 (1): 12–20.
^ abcBalakumar P, Rohilla A, Krishan P, Solairaj P, Thangathirupathi A (June 2010). "The multifaceted therapeutic potential of benfotiamine". Pharmacological Research. 61 (6): 482–488. doi:10.1016/j.phrs.2010.02.008. PMID 20188835.
^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". Molecular and Cellular Neurosciences. 55: 17–25. doi:10.1016/j.mcn.2012.09.001. PMC3609887. PMID 22982063.
March 10, 2023
benfotiamine, rinn, benzoylthiamine, monophosphate, synthetic, soluble, acyl, derivative, thiamine, vitamin, that, approved, some, countries, medication, dietary, supplement, treat, diabetic, sensorimotor, polyneuropathy, developed, late, 1950s, japan, clinica. 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 BenfotiamineClinical dataTrade namesMilgammaOther namesS Benzoylthiamine O monophosphateAHFS Drugs comInternational Drug NamesRoutes ofadministrationOralATC codeA11DA03 WHO Legal statusLegal statusIn general Over the counter OTC IdentifiersIUPAC name S 2 4 Amino 2 methylpyrimidin 5 yl methyl formyl amino 5 phosphonooxy pent 2 en 3 yl benzenecarbothioateCAS Number22457 89 2 YPubChem CID3032771ChemSpider2297665 YUNIIY92OUS2H9BChEBICHEBI 41039 NChEMBLChEMBL1491875 NCompTox Dashboard EPA DTXSID3045433ECHA InfoCard100 040 906Chemical and physical dataFormulaC 19H 23N 4O 6P SMolar mass466 45 g mol 13D model JSmol Interactive imageSMILES O P O O OCCC SC O c1ccccc1 C N C O Cc2cnc nc2N C CInChI 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 YKey BTNNPSLJPBRMLZ LGMDPLHJSA N Y N Y what is this verify Contents 1 Uses 2 Adverse effects 3 Pharmacology 4 Chemistry 5 Research 6 See also 7 ReferencesUses EditBenfotiamine is primarily marketed as an over the counter drug to treat diabetic polyneuropathy 3 A 2021 review described two clinical trials with positive results for diabetic polyneuropathy and concluded that more research is needed 4 As of 2017 benfotiamine was marketed as a pharmaceutical drug in many countries under the following brand names Benalgis Benfogamma Benforce Benfotiamina Biotamin Biotowa Milgamma and Vilotram 5 It was also marketed in some jurisdictions as a combination drug with cyanocobalamin as Milgamma in combination with pyridoxine as Milgamma in combination with metformin as Benforce M and with thiamine as Vitafos 5 Adverse effects EditThere is little published data on adverse effects In one study of a combination of benfotiamine pyridoxine and cyanocobalamin around 8 of people taking the drug experienced nausea dizziness stomach ache and weight gain 6 Pharmacology EditBenfotiamine is dephosphorylated to S benzoylthiamine by ecto alkaline phosphatases present in the intestinal mucosa and is then hydrolyzed to thiamine by thioesterases in the liver 7 Benfotiamine is more bioavailable than thiamine salts 8 providing higher levels of thiamine in muscle brain liver and kidney 6 Benfotiamine mainly acts on peripheral tissues through an increase in transketolase activity 7 6 9 Chemistry EditBenfotiamine is a lipid derivative of thiamine specifically a synthetic S acyl Vitamin B1 analogue its chemical name is S benzoylthiamine O monophosphate 10 It has very low solubility in water or other aqueous solvents 7 Research EditBenfotiamine has been studied in laboratory models of diabetic retinopathy neuropathy and nephropathy 10 A 2021 review of its use for diabetic polyneuropathy described two clinical trials which showed improvements in neuropathic pain and neuropathic symptoms scores the latter of which showed a dose response effect 4 The authors concluded that it could potentially serve as an economical supplement to enhance neuropathy treatment and that more research is needed Administration of benfotiamine may increase intracellular levels of thiamine diphosphate a cofactor of transketolase 10 Based on metabolic theories of Alzheimer s disease since thiamine dependent processes are critical in glucose metabolism and are diminished in brains of Alzheimer s disease patients at autopsy and since treatment of mouse models of Alzheimer s disease with benfotiamine diminishes plaques decreases phosphorylation of tau and reverses memory deficits benfotiamine administration has been proposed as a possible intervention to reverse biological and clinical processes of Alzheimer s disease 11 See also EditVitamin B1 analoguesReferences Edit 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 McCarty MF Inoguchi T 2008 11 Targeting Oxidant Stress as a Strategy for Preventing Vascular Complications of Diabetes and Metabolic Syndrome In Pasupuleti VK Anderson JW eds Nutraceuticals glycemic health and type 2 diabetes 1st ed Ames Iowa Wiley Blackwell IFT Press p 213 ISBN 9780813804286 a b Zaheer A Zaheer F Saeed H Tahir Z Tahir MW April 2021 A Review of Alternative Treatment Options in Diabetic Polyneuropathy Cureus 13 4 e14600 doi 10 7759 cureus 14600 PMC 8139599 PMID 34040901 a b Benfotiamine International brands Drugs com Retrieved 14 March 2017 a b c 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 PDF The EFSA Journal 864 1 31 a b c Patel SM Patel RP Prajapati BG March 2012 Patel S ed Solubility enhancement of benfotiamine a lipid derivative of thiamine by solid dispersion technique Journal of Pharmacy amp Bioallied Sciences J Pharm Bioallied Sci 4 Suppl 1 S104 S105 doi 10 4103 0975 7406 94157 PMC 3467834 PMID 23066179 Bitsch R Wolf M Moller J Heuzeroth L Gruneklee D 1991 Bioavailability assessment of the lipophilic benfotiamine as compared to a water soluble thiamin derivative Annals of Nutrition amp Metabolism 35 5 292 296 doi 10 1159 000177659 PMID 1776825 Yamazaki M 1968 Studies on the absorption of S benzoylthiamine O monophosphate I Metabolism in tissue homogenates Vitamins 38 1 12 20 a b c Balakumar P Rohilla A Krishan P Solairaj P Thangathirupathi A June 2010 The multifaceted therapeutic potential of benfotiamine Pharmacological Research 61 6 482 488 doi 10 1016 j phrs 2010 02 008 PMID 20188835 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 Molecular and Cellular Neurosciences 55 17 25 doi 10 1016 j mcn 2012 09 001 PMC 3609887 PMID 22982063 Retrieved from https en wikipedia org w index php title Benfotiamine amp oldid 1134306906, wikipedia, wiki, book, books, library,
