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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H13ClN2O3S
Molecular Weight 276.74
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORPROPAMIDE

SMILES

CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1

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
[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
Tolazamide-induced cholestasis.
1980 Aug
Hypoglycemic coma, jaundice, and pure RBC aplasia following chlorpropamide therapy.
1980 May
Chlorpropamide-induced pure RBC aplasia.
1980 May
Chlorpropamide-induced haemolytic anaemia.
1981 Jan
Chlorpropamide-induced Syndrome of Inappropriate Antidiuretic Hormone Secretion.
1981 Jul
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
Chlorpropamide-induced cholestatic jaundice and pseudomembranous colitis.
1985 May
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
Correlating structure and function in ATP-sensitive K+ channels.
1998 Jul
The structure and function of the ATP-sensitive K+ channel in insulin-secreting pancreatic beta-cells.
1999 Apr
Effect of pressure up to 5.5GPa on dry powder samples of chlorpropamide form-A.
2006 Dec 11
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
A conformational polymorphic transition in the high-temperature epsilon-form of chlorpropamide on cooling: a new epsilon'-form.
2009 Dec
Metformin use and prostate cancer in Caucasian men: results from a population-based case-control study.
2009 Nov
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 IMPURITY]
Common Name English
CHLORPROPAMIDE [USP-RS]
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 [WHO-DD]
Common 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
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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 Dec 15 15:21:56 UTC 2023 , Edited by admin on Fri Dec 15 15:21:56 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID9020322
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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
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PRIMARY
RXCUI
2404
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PRIMARY RxNorm
CHEBI
3650
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PRIMARY
DRUG BANK
DB00672
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PRIMARY
PUBCHEM
2727
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PRIMARY
INN
790
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PRIMARY
NSC
626720
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PRIMARY
RS_ITEM_NUM
1126009
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PRIMARY
ChEMBL
CHEMBL498
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PRIMARY
SMS_ID
100000081875
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PRIMARY
NSC
44634
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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