Benfotiamine

Modify Date: 2024-01-02 16:44:40

Benfotiamine Structure
Benfotiamine structure
Common Name Benfotiamine
CAS Number 22457-89-2 Molecular Weight 466.448
Density 1.4±0.1 g/cm3 Boiling Point 745.1±70.0 °C at 760 mmHg
Molecular Formula C19H23N4O6PS Melting Point 165ºC
MSDS Chinese USA Flash Point 404.4±35.7 °C

 Use of Benfotiamine


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.

 Names

Name benfotiamine
Synonym More Synonyms

 Benfotiamine 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
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

 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

 Articles32

More 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...

 Synonyms

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
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