Benfotiamine

{{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 | image2 = Benfotiamine ball-and-stick.png | tradename = Milgamma | Drugs.com = International Drug Names | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = OTC | routes_of_administration = Oral | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref =  ☑Y | CAS_number = 22457-89-2 | ATC_prefix = A11 | ATC_suffix = DA03 | PubChem = 3032771 | ChEMBL_Ref =  ☒N | ChEMBL = 1491875 | ChEBI_Ref =  ☒N | ChEBI = 41039 | ChemSpiderID_Ref =  ☑Y | ChemSpiderID = 2297665 | UNII_Ref =  ☑Y | UNII = Y92OUS2H9B | synonyms = S-Benzoylthiamine O-monophosphate | C=19 | H=23 | N=4 | O=6 | P=1 | S=1 | molecular_weight = 466.448 g/mol | smiles = O=P(O)(O)OCCC(/SC(=O)c1ccccc1)=C(/N(C=O)Cc2cnc(nc2N)C)C | StdInChI_Ref =  ☑Y | StdInChI = 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- | StdInChIKey_Ref =  ☑Y | StdInChIKey = BTNNPSLJPBRMLZ-LGMDPLHJSA-N }}

Benfotiamine (rINN, or S-benzoylthiamine O-monophosphate) is a synthetic S-acyl derivative of thiamine (vitamin B1).

It is marketed as a dietary supplement in most of the developed world, and as a pharmaceutical drug in some countries for treating diabetic neuropathy under the trade name Milgamma and others. Combination drugs with pyridoxine or cyanocobalamin are also marketed in a few countries.

Uses

Benfotiamine is primarily marketed as an antioxidant dietary supplement.

In some countries it is marketed as a drug to treat diabetic neuropathy;[1] clinical trials results are mixed, finding it mildly useful or no different from placebo.[2][3]

Adverse effects

There is little published data on adverse effects; in one study of a combination drug of benfotiamine, pyridoxine, and cyanocobalamin, around 8% of people taking the drug experienced nausea, dizziness, stomach ache and weight gain.[4]

Pharmacology

Benfotiamine is more bioavailable than thiamine salts, providing higher levels of thiamine in muscle, brain, liver, and kidney.[4]

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.[5]

Benfotiamine mainly acts on peripheral tissues through an increase in transketolase activity.[5][4][6]

Chemistry

Benfotiamine is a synthetic S-acyl Vitamin B1 analogue; its chemical name is S-benzoylthiamine O-monophoshate.[7] Benfotiamin is a lipid derivative of thiamine vitamin. It has very low solubility in water or other aqueous solvents. .[5]

Society and culture

As of 2017, benfotiamine was marketed as a pharmaceutical drug in Argentina, Bosnia & Herzegowina, Bulgaria, Colombia, Czech Republic, Estonia, Georgia, Germany, Hong Kong, Hungary, India, Indonesia, Japan, Latvia, Lithuania, Poland, Portugal, Romania, Serbia, Slovakia, Slovenia, Russian Federation, Taiwan, and Vietnam under the following brand names: Benalgis, Benfogamma, Benforce, Benfotiamina, Biotamin, Biotowa, Milgamma, and Vilotram.[8]

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.[8]

Research

Benfotiamine has been studied in laboratory models of diabetic retinopathy, neuropathy, and nephropathy,[9] As of 2015 there had been one clinical study of benfotiamine in diabetic nephropathy.[10]

Administration of benfotiamine may increase intracellular levels of thiamine diphosphate, a cofactor of transketolase,[9] and based on metabolic theories of Alzheimers, it has been studied in preclinical models of Alzheimers disease.[11]

References

  1. ↑ McCarty, Mark F.; Inoguchi, Toyoshi (2008). "11. Targeting Oxidant Stress as a Strategy for Preventing Vascular Complications of Diabetes and Metabolic Syndrome". In Pasupuleti, Vijai K.; Anderson, James W. Nutraceuticals, glycemic health and type 2 diabetes (1st ed.). Ames, Iowa: Wiley-Blackwell/IFT Press. p. 213. ISBN 9780813804286.
  2. ↑ Javed, S; Alam, U; Malik, RA (December 2015). "Burning through the pain: treatments for diabetic neuropathy". Diabetes, obesity & metabolism. 17 (12): 1115–25. doi:10.1111/dom.12535. PMID 26179288.
  3. ↑ Javed, S; Petropoulos, IN; Alam, U; Malik, RA (January 2015). "Treatment of painful diabetic neuropathy". Therapeutic advances in chronic disease. 6 (1): 15–28. doi:10.1177/2040622314552071. PMC 4269610. PMID 25553239.
  4. 1 2 3 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.
  5. 1 2 3 Patel, S, ed. (2012). Solubility enhancement of benfotiamine, a lipid derivative of thiamine by solid dispersion technique. US National Library of Medicine and National Institutes of Health: J Pharm Bioallied Sci. PMC 3467834.
  6. ↑ Yamazaki, M (1968). "Studies on the absorption of S-benzoylthiamine O-monophosphate : (I) Metabolism in tissue homogenates". Vitamins. 38 (1): 12–20.
  7. ↑ Balakumar, P; Rohilla, A; Krishan, P; Solairaj, P; Thangathirupathi, A (June 2010). "The multifaceted therapeutic potential of benfotiamine". Pharmacological research. 61 (6): 482–8. doi:10.1016/j.phrs.2010.02.008. PMID 20188835.
  8. 1 2 "Benfotiamine International brands". Drugs.com. Retrieved 14 March 2017.
  9. 1 2 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.
  10. ↑ Raval, AD; Thakker, D; Rangoonwala, AN; Gor, D; Walia, R (12 January 2015). "Vitamin B and its derivatives for diabetic kidney disease". The Cochrane Database of Systematic Reviews. 1: CD009403. doi:10.1002/14651858.CD009403.pub2. PMID 25579852.
  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". Molecular and cellular neurosciences. 55: 17–25. doi:10.1016/j.mcn.2012.09.001. PMC 3609887. PMID 22982063.
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