ベンフォチアミン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/10/21 00:31:50」(JST)
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Benfotiamine
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Systematic (IUPAC) name |
S-[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 |
? |
Identifiers |
CAS number |
22457-89-2 Y |
ATC code |
A11DA03 |
PubChem |
CID 3032771 |
ChemSpider |
2297665 Y |
UNII |
Y92OUS2H9B Y |
ChEBI |
CHEBI:41039 N |
Synonyms |
S-benzoylthiamine O-monophosphate |
Chemical data |
Formula |
C19H23N4O6PS |
Mol. mass |
466.448 g/mol |
SMILES
- O=P(O)(O)OCCC(/SC(=O)c1ccccc1)=C(/N(C=O)Cc2cnc(nc2N)C)C
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InChI
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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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N (what is this?) (verify)
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Benfotiamine (rINN, or S-benzoylthiamine O-monophosphate) is a synthetic S-acyl derivative of thiamine (vitamin B1).
It has been licensed for use in Germany since 1993. It is prescribed there for treating sciatica and other painful nerve conditions.[1]
It is marketed as a medicine and/or dietary supplement, depending on the respective Regulatory Authority.[citation needed]
Contents
- 1 Uses
- 2 Pharmacology
- 3 See also
- 4 References
- 5 External links
Uses[edit]
Benfotiamine is primarily marketed as an antioxidant dietary supplement. In a clinical study with six patients, benfotiamine lowered AGE by 40%.[2]
Benfotiamine may be useful for the treatment of diabetic retinopathy, neuropathy, and nephropathy however "Most of the effects attributed to benfotiamine are extrapolated from in vitro and animal studies. Unfortunately apparent evidences from human studies are scarce and especially endpoint studies are missing. Therefore additional clinical studies are mandatory to explore the therapeutic potential of benfotiamine in both diabetic and non-diabetic pathological conditions".[3] It is thought that treatment with benfotiamine leads to increased intracellular thiamine diphosphate levels,[3] 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.[4][5][6][7][8]
Pharmacology[edit]
After absorption, benfotiamine can be dephosphorylated by cells bearing an ecto-alkaline phosphatase to the lipid-soluble S-benzoylthiamine.[9] Benfotiamine should not be confused with allithiamine, a naturally occurring thiamine disulfide derivative with a distinct pharmacological profile.[10]
See also[edit]
- Allithiamine
- Fursultiamine
- Prosultiamine
- Sulbutiamine
References[edit]
- ^ "BBC news story: Back pain drug 'may aid diabetics'". 2003.
- ^ 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.
- ^ a b 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.
- ^ 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
External links[edit]
- BBC news story (2003): Back pain drug 'may aid diabetics'
Vitamins (A11)
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Fat soluble |
A
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α-Carotene · β-Carotene · Retinol# · Tretinoin
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D
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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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E
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Tocopherol (Alpha, Beta, Gamma, Delta) · Tocotrienol (Alpha, Beta, Gamma, Delta) · Tocofersolan
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K
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Naphthoquinone · Phylloquinone (K1) · Menaquinones (K2) · Menadione (K3)‡ · Menadiol (K4)
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Water soluble |
B
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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, L-methylfolate) · B12 (Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide) · Choline
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C
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Ascorbic acid# · Dehydroascorbic acid
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Combinations |
Multivitamins
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco, nuvi, sysi/epon, met
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English Journal
- Double-blind, randomized placebo-controlled clinical trial of benfotiamine for severe alcohol dependence.
- Manzardo AM1, He J, Poje A, Penick EC, Campbell J, Butler MG.
- Drug and alcohol dependence.Drug Alcohol Depend.2013 Dec 1;133(2):562-70. doi: 10.1016/j.drugalcdep.2013.07.035. Epub 2013 Aug 11.
- Alcohol dependence is associated with severe nutritional and vitamin deficiency. Vitamin B1 (thiamine) deficiency erodes neurological pathways that may influence the ability to drink in moderation. The present study examines tolerability of supplementation using the high-potency thiamine analog, ben
- PMID 23992649
- A randomized, double-blind, crossover, placebo-controlled trial of 6 weeks benfotiamine treatment on postprandial vascular function and variables of autonomic nerve function in Type 2 diabetes.
- Stirban A1, Pop A, Tschoepe D.
- Diabetic medicine : a journal of the British Diabetic Association.Diabet Med.2013 Oct;30(10):1204-8. doi: 10.1111/dme.12240. Epub 2013 Jun 12.
- AIMS: In a pilot study we suggested that benfotiamine, a thiamine prodrug, prevents postprandial endothelial dysfunction in people with Type 2 diabetes mellitus. The aim of this study was to test these effects in a larger population.METHODS: In a double-blind, placebo-controlled, randomized, crossov
- PMID 23701274
- Variability of skin autofluorescence measurement over 6 and 12 weeks and the influence of benfotiamine treatment.
- Stirban A1, Pop A, Fischer A, Heckermann S, Tschoepe D.
- Diabetes technology & therapeutics.Diabetes Technol Ther.2013 Sep;15(9):733-7. doi: 10.1089/dia.2013.0103. Epub 2013 Aug 21.
- BACKGROUND: Measurements of skin autofluorescence (SAF) allow for a simple and noninvasive quantification of tissue advanced glycation end-products (AGEs), a marker linked to the risk of diabetes complications. The aim of this study was to test the repeatability of SAF over 6 and 12 weeks and to tes
- PMID 23964994
Related Links
- ベンフォチアミン(Benfothiamine)のスペック詳細。ベンフォチアミンの製造・販売しています。 TOP > 主要生産品目> ベンフォチアミン 主な原薬を掲載しております。各品目に関するお問い合わせはこちらまでご連絡ください ...
- 1. Srp Arh Celok Lek. 2009 Nov-Dec;137(11-12):594-600. [The effect of benfothiamine in the therapy of diabetic polyneuropathy]. [Article in Serbian] Nikolić A, Kacar A, Lavrnić D, Basta I, Apostolski S. INTRODUCTION: Diabetic ...
Related Pictures
★リンクテーブル★
[★]
- 英
- benfotiamine, benfothiamine
- 商
- ビオタミン、ビオトーワ、シグマビタン、ダイメジンスリービー 、ビタメジン
- 関
- ビタミンB1