Chlorpropamide

Title: Chlorpropamide
CAS Registry Number: 94-20-2
CAS Name: 4-Chloro-N-[(propylamino)carbonyl]benzenesulfonamide
Additional Names: 1-(p-chlorophenylsulfonyl)-3-propylurea; 1-(p-chlorobenzenesulfonyl)-3-propylurea; N-propyl-N¢-(p-chlorobenzenesulfonyl)urea
Manufacturers' Codes: P-607
Trademarks: Adiaben; Asucrol; Catanil (DeAngeli); Chloronase (Hoechst); Diabechlor; Diabenal; Diabetoral (Boehringer, Mann.); Diabinese (Pfizer); Melitase (Berk); Millinese (Lampugnani); Oradian (Chinoin); Stabinol (Horner)
Molecular Formula: C10H13ClN2O3S
Molecular Weight: 276.74
Percent Composition: C 43.40%, H 4.73%, Cl 12.81%, N 10.12%, O 17.34%, S 11.59%
Literature References: Prepn: Marshall, Sigal, J. Org. Chem. 23, 927 (1958); GB 853555; W. M. McLamore, US 3349124 (1960, 1967 both to Pfizer); Bauer et al., J. Org. Chem. 31, 3440 (1960). Pharmacology and metabolism: Khurana et al., Indian J. Med. Res. 55, 1084 (1967); Brotherton et al., Clin. Pharmacol. Ther. 10, 505 (1969); Madsen et al., Eur. J. Pharmacol. 13, 374 (1971). Toxicity study: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).
Properties: Crystals from dil ethanol, mp 127-129°. uv max (0.01N HCl): 232.5 nm (e 16500). Soly in water at pH 6: 2.2 mg/ml. Practically insol at pH 7.3. Sol in alc; moderately sol in chloroform; sparingly sol in ether, benzene. LD50 i.p. in rats: 580 mg/kg (Goldenthal).
Melting point: mp 127-129°
Absorption maximum: uv max (0.01N HCl): 232.5 nm (e 16500)
Toxicity data: LD50 i.p. in rats: 580 mg/kg (Goldenthal)
Therap-Cat: Antidiabetic.
Keywords: Antidiabetic; Sulfonylurea Derivatives.
Chlorpropham Chlorprothixene Chlorpyrifos Chlorquinaldol Chlorsulfuron

Chlorpropamide
Chlorpropamide.svg
Chlorpropamide ball-and-stick.png
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. C
Legal status  ?
Routes Oral
Pharmacokinetic data
Bioavailability >90%
Protein binding 90%
Metabolism <1%
Half-life 36 hours
Excretion Renal (glomerular filtration → reabsorption → tubular secretion)
Identifiers
CAS number 94-20-2 YesY
ATC code A10BB02
PubChem CID 2727
DrugBank DB00672
ChemSpider 2626 YesY
UNII WTM2C3IL2X YesY
KEGG D00271 YesY
ChEBI CHEBI:3650 YesY
ChEMBL CHEMBL498 YesY
Chemical data
Formula C10H13ClN2O3S 
Mol. mass 276.74 g/mol
Physical data
Melt. point 126–130 °C (259–266 °F)
 YesY (what is this?)  (verify)

Chlorpropamide is a drug in the sulfonylurea class used to treat type 2 diabetes mellitus. It is a long-acting 1st generation sulfonylurea. It has more side effects than other sulfonylureas and its use is no longer recommended.[citation needed]