CAS 22457-89-2|Benfotiamine
| 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 | ChineseUSA | Flash Point | 404.4±35.7 °C |
Names
| Name | benfotiamine |
|---|---|
| Synonym | More Synonyms |
Benfotiamine BiologicalActivity
| 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 >>OthersNatural Products >>AlkaloidResearch 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 |
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 |
| InChIKey | BTNNPSLJPBRMLZ-GHRIWEEISA-N |
| SMILES | CC(=C(CCOP(=O)(O)O)SC(=O)c1ccccc1)N(C=O)Cc1cnc(C)nc1N |
| Storage condition | 2-8°C |
Toxicological Information
CHEMICAL IDENTIFICATION |
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 |
