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QuickView for Chlorpropamide (compound)


PubChem
Name: Chlorpropamide
PubChem Compound ID: 2727
Description: A sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277)
Molecular formula: C10H13ClN2O3S
Molecular weight: 276.741 g/mol
Synonyms:
Diabet-Pages; NCGC00015216-01; NCGC00015216-02; NSC626720; D00271; Spectrum2_000089; Prestwick0_000323; 1-(p-Chlorophenylsulfonyl)-3-propylurea; Prestwick1_000323; Urea, 1-[ (p-chlorophenyl)sulfonyl]-3-propyl-.
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DrugBank
Identification
Name: Chlorpropamide
Name (isomeric): DB00672
Drug Type: small molecule
Description: A sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277)
Synonyms:
Chlorporpamide
Brand: Melitase, Diabetoral, Diabaril, Mellinese, Diabenal, Insulase, Chloronase, Adiaben, Oradian, Glisema, Diabinese, Catanil, Glucamide, Diabet-Pages, Novo-Propamide, Apo-Chlorpropamide, Diabechlor, Chlorodiabina, Chlorpropamide Bp/ Usp, Diamel Ex, Diabeneza, Asucrol, Diabenese, Dynalase, Chlorpropamid, Chloropropamide, Stabinol, Meldian, Clorpropamide, Millinese
Category: Hypoglycemic Agents, Sulfonylureas, Antidiabetic
CAS number: 94-20-2
Pharmacology
Indication: For treatment of NIDDM in conjunction with diet and exercise.
Pharmacology: Chlorpropamide, a second-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Chlorpropamide is twice as potent as the related second-generation agent glipizide.
Mechanism of Action:
Sulfonylureas such as chlorpropamide bind to ATP-sensitive potassium channels on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secr...
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Absorption: Readily absorbed from the GI tract. Peak plasma concentrations occur within 2-4 hours and the onset of action occurs within one hour. The maximal effect of chlorpropamide is seen 3-6 hours following oral administration.
Protein binding: Highly bound to plasma proteins.
Biotransformation: Up to 80% of dose is metabolized likely through the liver to to 2-hydroxylchlorpropamide (2-OH CPA), p-chlorobenzenesulfonylurea (CBSU), 3-hydroxylchlorpropamide (3-OH CPA), and p-chlorobenzenesulfonamide (CBSA); CBSA may be produced by decomposition in urine. It is unknown whether chlorpropamide metabolites exert hypoglycemic effects.
Route of elimination: 80-90% of a single oral dose is excreted in the urine as unchaged drug and metabolites within 96 hours.
Half Life: Approximately 36 hours with interindividual variation ranging from 25-60 hours. Duration of effect persists for at least 24 hours.
Toxicity: IPN-RAT LD50 580 mg/kg
Affected organisms: Humans and other mammals
Interactions
Food interaction:
Take 30 minutes before meal.
Avoid alcohol.
Food reduces the rate of absorption.
Drug interaction:
OxprenololThe beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
BevantololThe beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
EsmololThe beta-blocker, esmolol, may decrease symptoms of hypoglycemia.
SulfadoxineSulfonamide/sulfonylurea: possible hypoglycemia
MetoprololThe beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
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