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.
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White to Off-White Solid
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The R-enantiomer showed only weak hypoglycemic activity. Repaglinide impurity
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Repaglinide is 2-ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid(Prandin); approvals for generics are pending. Combinationsare available with metformin in the United States(Prandimet), and the drug may also be coprescribed with oneof the thiazolidinediones (typically pioglitazone or rosiglitazone;see previous discussion). To establish the most clinicallyvaluable dose, the patient is titrated while monitoringblood glucose levels and hemoglobin glycosylation (HbA1c)as an index of longer-term overall control.
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K ATP channel blocker that binds with high affinity for SUR1 when co-expressed with Kir6.2 (K d = 0.42 nM). Antidiabetic glucose regulator with hypoglycaemic effect in vivo .
Clinical Use
Repaglinide is a nonsulfonylurea insulin secretagogue that was introduced in the United States in 1998 for type 2 diabetes.
