Repaglinide , ≥99% , 135062-02-1

Synonym(s):
(S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid;Novonorm;Prandin;Repaglinide

CAS NO.：135062-02-1

Empirical Formula: C27H36N2O4

Molecular Weight: 452.59

MDL number: MFCD00906179

EINECS: 629-921-1

PRODUCT Properties

• Melting point: 129-130.2 °C
• alpha: D20 +6.97° (c = 0.975 in methanol); D20 +7.45° (c = 1.06 in methanol)
• Boiling point: 672.9±55.0 °C(Predicted)
• Density: 1.137±0.06 g/cm3(Predicted)
• storage temp.: 2-8°C
• solubility: DMSO: 34 mg/mL
• form: solid
• pka: 4.19±0.10(Predicted)
• color: white
• Water Solubility: 89.99mg/L(25 ºC)
• Merck: 14,8136
• InChIKey: FAEKWTJYAYMJKF-QHCPKHFHSA-N
• SMILES: C(O)(=O)C1=CC=C(CC(N[C@H](C2=CC=CC=C2N2CCCCC2)CC(C)C)=O)C=C1OCC

Description and Uses

Repaglinide was marketed in the US as an orally active hypoglycemic agent in patients with a type Ⅱ diabetes mellitus, to lower blood glucose in synergistic combination with metformin, when hyperglycemia cannot be controlled by diet, exercise or metformin alone. Chiral (S)-repaglinide can be synthesized in several ways, each involving a stereoselective reduction of an imine or enamine group. Repaglinide is a nonsulfonylurea belonging to the meglitinide family, with an insulin-releasing effect mediated by pancreatic betacells, by closing the ATP-sensitive K+ channels that, in turn, increases the cytosolic concentration of Ca++. In several animal models, repaglinide was more efficient than glibenclamide as a dose-dependant promoter of insulin release, but its mechanism of action is probably slightly different. Repaglinide has a rapid onset of action, a short duration of action and a reduced risk of hypoglycemia compared to glyburide.

A KIR6 (KATP) channel blocker

Safety

• Symbol(GHS): GHS07,GHS08
• Signal word: Warning
• Hazard statements: H302-H361-H362
• Precautionary statements: P501-P263-P260-P270-P202-P201-P264-P280-P308+P313-P301+P312+P330-P405
• WGK Germany: 2
• RTECS: 000000033825
• HS Code: 2933399090
• Toxicity: LD50 orally in rats: >1 g/kg (Grell)