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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/08 11:54:47」(JST)

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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 under the trade name Milgamma. (Combinations with pyridoxine or cyanocobalamin are also sold under this name.) 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]}

Uses

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

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]

References

^ "BBC news story: Back pain drug 'may aid diabetics'". BBC News. 18 February 2003.
^ J Lin, A Alt, J Liersch, RG Bretzel, M Brownlee (May 2000). "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. doi:10.1038/nm834.
^ 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.
^ Volvert, M.L.; Seyen, S.; Piette, M.; Evrard, B.; Gangolf, M.; Plumier, J.C.; Bettendorff, L. (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 (1): 10. doi:10.1186/1471-2210-8-10.

External links

BBC news story (2003): Back pain drug 'may aid diabetics'

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 糖尿病性多発性神経障害の病因および予防 pathogenesis and prevention of diabetic polyneuropathy
2. プロテインキナーゼCと糖尿病の血管合併症 protein kinase c and the vascular complications of diabetes mellitus

English Journal

Effects of benfotiamine and coenzyme Q10 on kidney damage induced gentamicin.

Ustuner MA1, Kaman D2, Colakoglu N3.
Tissue & cell.Tissue Cell.2017 Oct 12. pii: S0040-8166(17)30063-0. doi: 10.1016/j.tice.2017.10.001. [Epub ahead of print]
PMID 29066103

d-Ribose as a Contributor to Glycated Haemoglobin.

Chen X1, Su T1, Chen Y2, He Y1, Liu Y1, Xu Y2, Wei Y3, Li J4, He R5.
EBioMedicine.EBioMedicine.2017 Oct 5. pii: S2352-3964(17)30393-6. doi: 10.1016/j.ebiom.2017.10.001. [Epub ahead of print]
PMID 29033370

Advances in the management of diabetic neuropathy.

Várkonyi T1, Körei A2, Putz Z2, Martos T2, Keresztes K3, Lengyel C4, Nyiraty S4, Stirban A5, Jermendy G6, Kempler P2.
Minerva medica.Minerva Med.2017 Oct;108(5):419-437. doi: 10.23736/S0026-4806.17.05257-0. Epub 2017 May 25.
PMID 28541026

Japanese Journal

Significance of Advanced Glycation End Products in Aging-Related Disease

Nagai Ryoji,Mori Takefumi,Yamamoto Yasuhiko,Kaji Yuichi,Yonei Yoshikazu
ANTI-AGING MEDICINE 7(10), 112-119, 2010
… and inhibitors for AGE generation, such as aminoguanidine, pyridoxamine, and benfotiamine, delay the pathogenesis of diabetic nephropathy and retinopathy. …
NAID 130000428490

糖尿病とベンフォチアミン

田鶴谷(村山) 恵子,山田和子,三嶋基弘
ビタミン 82(2), 137-139, 2008-02-25
NAID 110006596185

Regulation of intracellular glucose and polyol pathway by thiamine and benfotiamine in vascular cells cultured in high glucose

BERRONE E
J Biol Chem 281, 9307-9313, 2006
NAID 80019231506

「ベンフォチアミン」

Benfotiamine
Systematic (IUPAC) name
	S-[2-{[(4-Amino-2-methylpyrimidin-5-yl)methyl] (formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate
Clinical data
Trade names	Milgamma
AHFS/Drugs.com	International Drug Names
Legal status	OTC;
Routes of; administration	Oral
Identifiers
CAS Registry Number	22457-89-2
ATC code	A11DA03
PubChem	CID: 3032771
ChemSpider	2297665
UNII	Y92OUS2H9B
ChEBI	CHEBI:41039
ChEMBL	CHEMBL1491875
Synonyms	S-Benzoylthiamine O-monophosphate
Chemical data
Formula	C19H23N4O6PS
Molecular mass	466.448 g/mol
	SMILES O=P(O)(O)OCCC(/SC(=O)c1ccccc1)=C(/N(C=O)Cc2cnc(nc2N)C)C ;
	InChI 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- ; Key:BTNNPSLJPBRMLZ-LGMDPLHJSA-N ;
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　　[★]

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

[BBC2003-1] "BBC news story: Back pain drug 'may aid diabetics'". BBC News. 18 February 2003.

[Lin-2] J Lin, A Alt, J Liersch, RG Bretzel, M Brownlee (May 2000). "Benfotiamine Inhibits Intracellular Formation of Advanced Glycation End Products in vivo". Diabetes. 49 (Suppl1) (A143): 583.

[pmid20188835-3] 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.

[4] 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. doi:10.1038/nm834.

[pmid17630265-5] 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.

[pmid11571671-6] 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.

[pmid16936154-7] 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.

[pmid12882930-8] 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.

[9] Yamazaki, M (1968). "Studies on the absorption of S-benzoylthiamine O-monophosphate : (I) Metabolism in tissue homogenates". Vitamins 38 (1): 12–20.

[10] Volvert, M.L.; Seyen, S.; Piette, M.; Evrard, B.; Gangolf, M.; Plumier, J.C.; Bettendorff, L. (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 (1): 10. doi:10.1186/1471-2210-8-10.

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benfotiamine