U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H13ClN2O3S
Molecular Weight 276.7412
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORPROPAMIDE

SMILES

CCCN=C(NS(=O)(=O)c1ccc(cc1)Cl)O

InChI

InChIKey=RKWGIWYCVPQPMF-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68002747

Chlorpropamide (DIABINESE®), is a sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. It appears to lower the blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. The mechanism by which chlorpropamide (DIABINESE®) lowers blood glucose during long-term administration has not been clearly established. Extra-pancreatic effects may play a part in the mechanism of action of oral sulfonylurea hypoglycemic drugs. While chlorpropamide is a sulfonamide derivative, it is devoid of antibacterial activity. Chlorpropamide (DIABINESE®) may also prove effective in controlling certain patients who have experienced primary or secondary failure to other sulfonylurea agent.

Originator

Curator's Comment:: # Pfizer Inc.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.04 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIABINESE

Approved Use

Chlorpropamide tablets are indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.

Launch Date

-3.52771211E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
28.5 μg/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROPAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
545 μg × h/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROPAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
33.1 h
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPROPAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >1000 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >200 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
yes [Inhibition 100 uM]
yes
yes
yes
yes
yes
yes
yes
yes
Drug as victimTox targets
PubMed

PubMed

TitleDatePubMed
Haemolysis and agranulocytosis complicating treatment with methyldopa.
1967 Oct 14
Pure red blood cell aplasia associated with chlorpropamide therapy. Patient summary and review of the literature.
1969 Apr
Chlorpropamide-induced immune hemolytic anemia.
1970 Oct 22
Severe hypoglycaemic shock caused by chlorpropamide. (Case report).
1971 Jan
Inappropriate secretion of antidiuretic hormone induced by chlorpropamide.
1972 Mar
Chlorpropamide and angina pectoris.
1973 Mar
[Case of hypoglycemic coma in a female patient with diabetes insipidus treated with chlorpropamide].
1974 Jan-Feb
Encephalopathy induced by oral hypoglycemic drugs.
1977 Aug
Chlorpropamide-alcohol flushing: a definition of its relation to non-insulin-dependent diabetes.
1978 Dec 2
Reduction of the severity of nephropathy in aging Fischer 344 rats treated with analogs of arylsulfonyluria.
1979 Jul
Chlorpropamide induced syndrome of inappropriate antidiuretic hormone secretion.
1980 Apr
Tolazamide-induced cholestasis.
1980 Aug
Hypoglycemic coma, jaundice, and pure RBC aplasia following chlorpropamide therapy.
1980 May
Chlorpropamide-induced pure RBC aplasia.
1980 May
Megaloblastic anaemia due to vitamin B12 malabsorption associated with long-term metformin treatment.
1980 May 17
Chlorpropamide-induced haemolytic anaemia.
1981 Jan
Chlorpropamide-induced Syndrome of Inappropriate Antidiuretic Hormone Secretion.
1981 Jul
Chlorpropamide-induced optic neuropathy.
1982 Feb
Chlorpropamide-induced hypoglycemia. A dramatic presentation of celiac disease.
1982 Feb 12
Nephrotic syndrome and immune complex glomerulonephritis associated with chlorpropamide therapy.
1983 Feb
The effect of chlorpropamide hyponatremia on mental status in a nursing home population.
1983 May
Chlorpropamide-induced hemolytic anemia.
1984 Dec
Acute hemolytic anemia associated with a chlorpropamide-induced apparent auto-anti-Jka.
1984 May-Jun
Incidence of severe sideeffects during therapy with sulfonylureas and biguanides.
1985
A case of chronic liver disease due to tolazamide.
1985 Jul
Chlorpropamide-induced cholestatic jaundice and pseudomembranous colitis.
1985 May
The mechanisms of sulfonylurea-induced immune hemolysis: case report and review of the literature.
1986 Nov
Prolonged cholestasis and disappearance of interlobular bile ducts following chlorpropamide and erythromycin ethylsuccinate. Case of drug interaction?
1988 Dec
Chlorpropamide induced syndrome of inappropriate secretion of antidiuretic hormone.
1991 Aug
Chlorpropamide or chlorpromazine?
1991 Jan 15
Chlorpropamide-induced hyponatremia in the veteran population.
1992 Oct
Hypertension secondary to chlorpropamide with amelioration by changing to insulin.
1993 Apr
Chlorpropamide-induced ADH release, hyponatremia and central pontine myelinolysis in diabetes mellitus.
1995 Dec
Reconstitution of IKATP: an inward rectifier subunit plus the sulfonylurea receptor.
1995 Nov 17
Chlorpropamide-induced cholestatic liver failure resulting in death.
1996 May-Jun
Correlating structure and function in ATP-sensitive K+ channels.
1998 Jul
Effects of prolonged in vitro exposure to sulphonylureas on the function and survival of human islets.
2005 Jan-Feb
Antiinflammatory, analgesic and hypoglycemic effects of Mangifera indica Linn. (Anacardiaceae) stem-bark aqueous extract.
2005 Oct
Effect of pressure up to 5.5GPa on dry powder samples of chlorpropamide form-A.
2006 Dec 11
Inhibition by natural dietary substances of gastrointestinal absorption of starch and sucrose in rats 2. Subchronic studies.
2007 Aug 10
Inhibition by natural dietary substances of gastrointestinal absorption of starch and sucrose in rats and pigs: 1. Acute studies.
2007 Aug 6
A new gamma-polymorph of chlorpropamide: 4-chloro-N-(propylaminocarbonyl)benzenesulfonamide.
2007 Jun
Studying the human brain anatomical network via diffusion-weighted MRI and Graph Theory.
2008 Apr 15
Chlorpropamide treatment restores the reduced carrageenan-induced paw edema and pleural exudate volume in diabetic rats.
2008 Sep
Comprehensive in silico prediction and analysis of chlamydial outer membrane proteins reflects evolution and life style of the Chlamydiae.
2009 Dec 29
Maitake mushroom extracts ameliorate progressive hypertension and other chronic metabolic perturbations in aging female rats.
2010 Jun 7
Ameliorative effects of Cnidoscolus aconitifolius on alloxan toxicity in Wistar rats.
2010 Sep
Epac2: a sulfonylurea receptor?
2012 Feb
Pharmacogenomic analysis of ATP-sensitive potassium channels coexpressing the common type 2 diabetes risk variants E23K and S1369A.
2012 Mar
A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans.
2014 Jan
Patents

Sample Use Guides

The mild to moderately severe, middle-aged, stable type 2 diabetes patient should be started on 250 mg daily. In elderly patients, debilitated or malnourished patients, and patients with impaired renal or hepatic function, the initial and maintenance dosing should be conservative to avoid hypoglycemic reactions. Older patients should be started on smaller amounts of DIABINESE®, in the range of 100 to 125 mg daily.
Route of Administration: Oral
The ATP-sensitive potassium channels containing the K23/A1369 risk haplotype were significantly less sensitive to inhibition by chlorpropamide (IC50 values for risk haplotype K23/A1369 vs. nonrisk haplotype E23/S1369 = 4.19 vs. 3.04 uM).
Name Type Language
CHLORPROPAMIDE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
CHLORPROPAMIDE [EP]
Common Name English
CHLORPROPAMIDE [USP-RS]
Common Name English
CHLORPROPAMIDE [WHO-DD]
Common Name English
CHLORPROPAMIDE [MI]
Common Name English
GLUCAMIDE
Brand Name English
CHLORPROPAMIDE [HSDB]
Common Name English
CHLORPROPAMIDE [INN]
Common Name English
CHLORPROPAMIDE [ORANGE BOOK]
Common Name English
NSC-44634
Code English
CHLORPROPAMIDE [MART.]
Common Name English
BENZENESULFONAMIDE, 4-CHLORO-N-((PROPYLAMINO)CARBONYL)-
Systematic Name English
CHLORPROPAMIDE [JAN]
Common Name English
1-((P-CHLOROPHENYL)SULFONYL)-3-PROPYLUREA
Common Name English
DIABINESE
Brand Name English
CHLORPROPAMIDE [VANDF]
Common Name English
NSC-626720
Code English
CHLORPROPAMIDE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
WHO-VATC QA10BB02
Created by admin on Fri Jun 25 20:57:38 UTC 2021 , Edited by admin on Fri Jun 25 20:57:38 UTC 2021
NDF-RT N0000008054
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WHO-ATC A10BB02
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NDF-RT N0000008054
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LIVERTOX 197
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NCI_THESAURUS C97936
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NDF-RT N0000175608
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NDF-RT N0000008054
Created by admin on Fri Jun 25 20:57:38 UTC 2021 , Edited by admin on Fri Jun 25 20:57:38 UTC 2021
Code System Code Type Description
EPA CompTox
94-20-2
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PRIMARY
NCI_THESAURUS
C47447
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PRIMARY
IUPHAR
6801
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PRIMARY
LACTMED
Chlorpropamide
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PRIMARY
CAS
94-20-2
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PRIMARY
WIKIPEDIA
CHLORPROPAMIDE
Created by admin on Fri Jun 25 20:57:38 UTC 2021 , Edited by admin on Fri Jun 25 20:57:38 UTC 2021
PRIMARY
RXCUI
2404
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PRIMARY RxNorm
DRUG BANK
DB00672
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PRIMARY
PUBCHEM
2727
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PRIMARY
INN
790
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PRIMARY
USP_CATALOG
1126009
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PRIMARY USP-RS
ChEMBL
CHEMBL498
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PRIMARY
FDA UNII
WTM2C3IL2X
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PRIMARY
ECHA (EC/EINECS)
202-314-5
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PRIMARY
MERCK INDEX
M3462
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PRIMARY Merck Index
EVMPD
SUB06209MIG
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PRIMARY
DRUG CENTRAL
622
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PRIMARY
HSDB
2051
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PRIMARY
MESH
D002747
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PRIMARY