- Chlorpropamide
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Chlorpropamide 
Systematic (IUPAC) name 4-chloro-N-(propylcarbamoyl)benzenesulfonamide Clinical data Trade names Diabinese AHFS/Drugs.com monograph MedlinePlus a682479 Licence data US FDA:link Pregnancy cat. ? Legal status ? Pharmacokinetic data Half-life 36 hours Identifiers CAS number 94-20-2 
ATC code A10BB02 PubChem CID 2727 DrugBank APRD00029 ChemSpider 2626 UNII WTM2C3IL2X KEGG D00271 ChEBI CHEBI:3650 ChEMBL CHEMBL498 Chemical data Formula C10H13ClN2O3S Mol. mass 276.74 g/mol SMILES eMolecules & PubChem - InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)
Key:RKWGIWYCVPQPMF-UHFFFAOYSA-N
(what is this?) (verify)Chlorpropamide is a drug in the sulphonylurea class used to treat type 2 diabetes mellitus. It is a long-acting sulphonylurea. It has more side effects than other sulphonylureas and its use is no longer recommended.
Mechanism of action
Like other sulfonylureas, chlorpropamide acts to increase the secretion of insulin, so it is only effective in patients who have some pancreatic beta cell function. It can cause relatively long episodes of hypoglycemia; this is one reason why shorter-acting sulfonylureas such as gliclazide or tolbutamide are used instead. The risk of hypoglycemia makes this drug a poor choice for the elderly and patients with mild to moderate hepatic and renal impairment. Chlorpropamide is also used in Partial Central Diabetes Insipidus.
Cautions and contraindications
Chlorpropamide and other sulphonylureas encourage weight gain, so they are generally not favored for use in very obese patients. Metformin (Glucophage) is considered a better drug for these patients. Sulfonylureas should be avoided in patients with hepatic and renal impairment, patients with porphyria, patients who are breastfeeding, and patients with ketoacidosis. Not indicated for patients more than 65 years of age.
Other side effects
Other side effects of chlorpropamide include gastrointestinal symptoms such as nausea, vomiting, diarrhea, and constipation. It may cause facial flushing after the ingestion of alcohol. It may increase secretion of antidiuretic hormone (ADH), which can lead to hyponatremia. It also markedly raises the serum level of alkaline phosphatase.
Oral anti-diabetic drugs and Insulin analogs (A10) Insulin K+ ATP1st generation: Acetohexamide • Carbutamide • Chlorpropamide • Tolbutamide • Tolazamide
2nd generation: Glibenclamide (Glyburide)# • Glipizide • Gliquidone • Glyclopyramide • Glimepiride • Gliclazide •Meglitinides/"glinides"GLP-1 analogsExenatide • Liraglutide • Taspoglutide† • Albiglutide† • LixisenatideAnalogs/other insulinsfast-acting (Insulin lispro • Insulin aspart • Insulin glulisine) • short-acting (Regular insulin) • long-acting (Insulin glargine • Insulin detemir • NPH insulin) • ultra-long-acting (Insulin degludec†) • inhalable Exubera‡Other Amylin analogSGLT2 inhibitorsCanagliflozin† • Dapagliflozin† • Remogliflozin§ • Sergliflozin§OtherBenfluorex‡ • Tolrestat‡Categories:- Sulfonylureas
- Organochlorides
- InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)
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