Benfotiamine

Names

[ Name ]:
Benfotiamine

[Synonym ]:
berdi
S-benzoylthiamine monophosphate
bietamine
biotamin
S-[(2Z)-2-{[(4-Amino-2-methyl-5-pyrimidinyl)methyl](formyl)amino}-5-(phosphonooxy)-2-penten-3-yl] benzenecarbothioate
betivina
S-Benzoyl-thiamin-monophosphat
EINECS 245-013-4
Benfotiamine
neurostop
S-Benzoylthiamine O-Monophosphate
8088c.b.
Benfotiaminum
S-Benzoyl-thiamin-O-monophosphat
S-benzoylthiamine-O-monophosphate
MFCD00057343
MilgaMMa
btmp
benzenecarbothioic acid, S-[(1Z)-2-[[(4-amino-2-methyl-5-pyrimidinyl)methyl]formylamino]-1-[2-(phosphonooxy)ethyl]-1-propen-1-yl] ester
nitanevril
tabiomyl

Biological Activity

[Description]:

Benfotiamine is a synthetic S-acyl derivative of thiamine (vitamin B1); an antioxidant dietary supplement.IC50 value:Target: Benfotiamine, the lipid-soluble thiamine derivative used as a treatment for diabetic neuropathy, can inhibit three major pathways(the hexosamine pathway, the advanced glycation end product (AGE) formation pathway and the diacylglycerol (DAG)?protein kinase C (PKC) pathway）of hyperglycemic damage and prevent experimental diabetic retinopathy. Benfotiamine is a synthetic S-acyl derivative of thiamine (vitamin B1) for treating sciatica and other painful nerve conditions. More effective at increasing thiamin levels in blood and tissues than water-soluble salts like the previous vitamin B1.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Neurological Disease

[References]

[1]. Tarallo S, Beltramo E, Berrone E, Porta M. Human pericyte-endothelial cell interactions in co-culture models mimicking the diabetic retinal microvascular environment. Acta Diabetol. 2012 Dec;49 Suppl 1:141-51.

[2]. Engelen L, Stehouwer CD, Schalkwijk CG. Current therapeutic interventions in the glycation pathway:Evidence from clinical studies. Diabetes Obes Metab. 2012 Dec 26.

[3]. Hurt JK, Coleman JL, Fitzpatrick BJ, et al. Prostatic acid phosphatase is required for the antinociceptive effects of thiamine and benfotiamine. PLoS One. 2012;7(10):e48562.

[4]. Hans-Peter Hammes, Xueliang Du, Diane Edelstein, et al. Benfotiamine blocks three major pathways of hyperglycemic damage and prevents experimental diabetic retinopathy. Nature Medicine, 2003, 9, 294 - 299

[5]. Loew D. Pharmacokinetics of thiamine derivatives especially of benfotiamine. International Journal of Clinical Pharmacology and Therapeutics, 1996, 34(2):47-50

[6]. Benfotiamine

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
745.1±70.0 °C at 760 mmHg

[ Melting Point ]:
165ºC

[ Molecular Formula ]:
C₁₉H₂₃N₄O₆PS

[ Molecular Weight ]:
466.448

[ Flash Point ]:
404.4±35.7 °C

[ Exact Mass ]:
466.107605

[ PSA ]:
191.05000

[ LogP ]:
1.81

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.645

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DH6910000

CHEMICAL NAME :: Benzoic acid, thio-, S-ester with N-((4-amino-2-methyl-5-pyrimidinyl)methyl)-N-(4-hydro xy- 2-mercapto-1-methyl-1-butenyl)formamide dihydrogen phosphate (ester)

CAS REGISTRY NUMBER :: 22457-89-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C19-H23-N4-O6-P-S

MOLECULAR WEIGHT :: 466.49

WISWESSER LINE NOTATION :: T6N CNJ B1 DZ E1VMY1&UYSVR&2OPQQO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,781,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85IPAE "Modern Pharmaceuticals of Japan, III," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1968 Volume(issue)/page/year: -,78,1968

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DH6910000

Articles

Benfotiamine, a synthetic S-acyl thiamine derivative, has different mechanisms of action and a different pharmacological profile than lipid-soluble thiamine disulfide derivatives.

BMC Pharmacol. 8 , 10, (2008)

Lipid-soluble thiamine precursors have a much higher bioavailability than genuine thiamine and therefore are more suitable for therapeutic purposes. Benfotiamine (S-benzoylthiamine O-monophosphate), a...

The detrimental effects of acute hyperglycemia on myocardial glucose uptake.

Life Sci. 105(1-2) , 31-42, (2014)

Although acute hyperglycemic (AHG) episodes are linked to lower glucose uptake, underlying mechanisms remain unclear. We hypothesized that AHG triggers reactive oxygen species (ROS) production and inc...

The effect of benfotiamine on mu-opioid receptor mediated antinociception in experimental diabetes.

Exp. Clin. Endocrinol. Diabetes 122(3) , 173-8, (2014)

Diabetic neuropathy is a prevalent, disabling disorder. Currently, the only treatments available to patients with diabetic neuropathy are glucose control and pain management. B vitamin present neuropr...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.