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Substance Name: Chlorpropamide [USP:INN:BAN:JAN]
RN: 94-20-2
UNII: WTM2C3IL2X
InChIKey: RKWGIWYCVPQPMF-UHFFFAOYSA-N

Note

  • 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

  • C10-H13-Cl-N2-O3-S

Molecular Weight

  • 276.7427
 

Classification Codes

  • Antidiabetic
  • Drug / Therapeutic Agent
  • Human Data
  • Hypoglycemic Agents
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • Chloropropamide
  • Chlorpropamide
  • Chlorpropamide [USP:INN:BAN:JAN]

MeSH Heading

  • Chlorpropamide

Synonyms

  • 1-((p-Chlorophenyl)sulfonyl)-3-propylurea
  • 1-(p-Chlorobenzenesulfonyl)-3-propylurea
  • 1-(p-Chlorobenzensulfonyl)-3-propylurea
  • 1-p-Chlorophenyl-3-(propylsulfonyl)urea
  • 1-Propyl-3-(p-chlorobenzenesulfonyl)urea
  • 4-11-00-00119 (Beilstein Handbook Reference)
  • 4-Chloro-4-((propylamino)carbonyl)benzenesulfonamide
  • 4-Chloro-N-((propylamino)carbonyl)benzenesulfonamide
  • Adiaben
  • Asucrol
  • Benzenesulfonamide, 4-chloro-N-((propylamino)carbonyl)-
  • Bioglumin
  • BRN 2218363
  • Catanil
  • CCRIS 155
  • Chlorodiabina
  • Chloronase
  • Chloropropamide
  • Chlorpropamid
  • Chlorpropamide
  • Chlorpropamidum
  • Chlorpropamidum [INN-Latin]
  • Clorpropamid
  • Clorpropamida
  • Clorpropamida [INN-Spanish]
  • Clorpropamide
  • Clorpropamide [DCIT]
  • Clorpropamide [Italian]
  • Diabaril
  • Diabechlor
  • Diabenal
  • Diabenese
  • Diabeneza
  • Diabet-pages
  • Diabetoral
  • Diabexan
  • Diabinese
  • Diamel Ex
  • Dynalase
  • EINECS 202-314-5
  • Glisema
  • Glucamide
  • HSDB 2051
  • Insogen
  • Insulase
  • Meldian
  • Melitase
  • Mellinese
  • Millinese
  • N-(4-Chlorophenylsulfonyl)-N'-propylurea
  • N-(p-Chlorobenzenesulfonyl)-N'-propylurea
  • N-Propyl-N'-(p-chlorobenzenesulfonyl)urea
  • N-Propyl-N'-p-chlorphenylsulfonylcarbamide
  • NCI-C01752
  • NSC 44634
  • NSC 626720
  • Oradian
  • P 607
  • Prodiaben
  • Stabinol
  • U-3818
  • U-9818
  • UNII-WTM2C3IL2X
  • Urea, 1-((p-chloropenyl)sulfonyl)-3-propyl-

Systematic Names

  • Benzenesulfonamide, 4-chloro-N-((propylamino)carbonyl)-
  • Chlorpropamide
  • Urea, 1-((p-chlorophenyl)sulfonyl)-3-propyl-

Superlist Name

  • Chlorpropamide

Registry Numbers

CAS Registry Number

  • 94-20-2

FDA UNII

  • WTM2C3IL2X

System Generated Number

  • 0000094202

Structure Descriptors

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)

InChIKey

RKWGIWYCVPQPMF-UHFFFAOYSA-N

Smiles

c1(S(=O)(=O)NC(=O)NCCC)ccc(cc1)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intraperitoneal 575mg/kg (575mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
dog LD50 oral 800mg/kg (800mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
human TDLo oral 300mg/kg/4W (300mg/kg)   JAMA, Journal of the American Medical Association. Vol. 238, Pg. 422, 1977.
human TDLo oral 300mg/kg/4W (300mg/kg) BLOOD: LEUKOPENIA

BLOOD: GRANULOCYTOPENIA		 JAMA, Journal of the American Medical Association. Vol. 238, Pg. 422, 1977.
mammal (species unspecified) LD50 oral 1039mg/kg (1039mg/kg)   Farmatsevtichnii Zhurnal Vol. (1), Pg. 51, 1985.
man TDLo oral 14mg/kg (14mg/kg)   Journal of Analytical Toxicology. Vol. 5, Pg. 287, 1981.
man TDLo oral 14mg/kg (14mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP Journal of Analytical Toxicology. Vol. 5, Pg. 287, 1981.
man TDLo oral 83mg/kg/25D-I (83mg/kg) LIVER: "JAUNDICE, CHOLESTATIC"

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE		 American Journal of Gastroenterology. Vol. 80, Pg. 381, 1985.
mouse LD50 intraperitoneal 409mg/kg (409mg/kg)   Toksikologicheskii Vestnik. Vol. (3), Pg. 36, 1995.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Progress in Medical Chemistry. Vol. 1, Pg. 187, 1961.
mouse LD50 oral 1100mg/kg (1100mg/kg)   French Demande Patent Document. Vol. #2184511,
rat LD50 intraperitoneal 580mg/kg (580mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intravenous 590mg/kg (590mg/kg)   Progress in Medical Chemistry. Vol. 1, Pg. 187, 1961.
rat LD50 oral 2150mg/kg (2150mg/kg)   Farmakologiya i Toksikologiya Vol. 25, Pg. 93, 1962.
women TDLo oral 25mg/kg/5D-I (25mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA Drug Intelligence and Clinical Pharmacy. Vol. 18, Pg. 981, 1984.
women TDLo oral 42mg/kg/7D-I (42mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA

BEHAVIORAL: GENERAL ANESTHETIC		 Postgraduate Medical Journal. Vol. 57, Pg. 44, 1981.
women TDLo oral 60mg/kg (60mg/kg) BEHAVIORAL: COMA

ENDOCRINE: HYPOGLYCEMIA		 Clinical Toxicology. Vol. 7, Pg. 19, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 128 deg C   EXP
pKa Dissociation Constant 5.13 (none)   EXP
log P (octanol-water) 2.27 (none)   EXP
Water Solubility 258 mg/L 37 EXP
Vapor Pressure 3.74E-08 mm Hg 25 EST
Henry's Law Constant 1.28E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.32E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.