ベンフォチアミン

Benfotiamine/ja

Clinical data
Trade names	Milgamma
Other names	S-Benzoylthiamine O-monophosphate
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	A11DA03 (WHO)
Legal status
Legal status	In general: Over-the-counter (OTC)
Identifiers
IUPAC name S-[2-{[(4-Amino-2-methylpyrimidin-5-yl)methyl] (formyl)amino}-5-(phosphonooxy)pent-2-en-3-yl] benzenecarbothioate
CAS Number	22457-89-2 Y
PubChem CID	3032771
ChemSpider	2297665 Y
UNII	Y92OUS2H9B
ChEBI	CHEBI:41039 N
ChEMBL	ChEMBL1491875 N
Chemical and physical data
Formula	C19H23N4O6PS
Molar mass	466.45 g·mol−1
3D model (JSmol)	Interactive image
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- Y Key:BTNNPSLJPBRMLZ-LGMDPLHJSA-N Y
NY (what is this?)  (verify)

ベンフォチアミン（Benfotiamine、rINN、またはS-ベンゾイルチアミンO-一リン酸）は、チアミン（ビタミンB1）の合成脂溶性S-アシル誘導体であり、一部の国では糖尿病性感覚運動性多発神経炎の治療薬または栄養補助食品として承認されている。ベンフォチアミンは1950年代後半に日本で開発された。

用途

ベンフォチアミンは、主に糖尿病性多発神経炎の治療薬として販売されている。2021年のレビューでは、糖尿病性多発神経炎に対して肯定的な結果を示した2つの臨床試験が記載され、さらなる研究が必要であると結論付けられている。

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. 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.

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.

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

Benfotiamine mainly acts on peripheral tissues through an increase in transketolase activity.

Chemistry

Benfotiamine is a lipid derivative of thiamine, specifically a synthetic S-acyl Vitamin B₁ analogue; its chemical name is S-benzoylthiamine O-monophosphate. It has very low solubility in water or other aqueous solvents.

Research

Benfotiamine has been studied in laboratory models of diabetic retinopathy, neuropathy, and nephropathy. 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. 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. 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.

See also

• Vitamin B₁ analogues