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

Molecular Formula C10H13ClN2O3S
Molecular Weight 276.74
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Chlorpropamide-induced immune hemolytic anemia.
1970 Oct 22
Inappropriate secretion of antidiuretic hormone induced by chlorpropamide.
1972 Mar
Chlorpropamide and angina pectoris.
1973 Mar
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
Hypoglycemic coma, jaundice, and pure RBC aplasia following chlorpropamide therapy.
1980 May
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
The effect of chlorpropamide hyponatremia on mental status in a nursing home population.
1983 May
Incidence of severe sideeffects during therapy with sulfonylureas and biguanides.
1985
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
Correlating structure and function in ATP-sensitive K+ channels.
1998 Jul
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.
2003 Aug
Inhibition by natural dietary substances of gastrointestinal absorption of starch and sucrose in rats 2. Subchronic studies.
2007 Aug 10
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
Quantitative 35Cl nuclear quadrupole resonance in tablets of the antidiabetic medicine Diabinese.
2009 Jul 1
Metformin use and prostate cancer in Caucasian men: results from a population-based case-control study.
2009 Nov
Maitake mushroom extracts ameliorate progressive hypertension and other chronic metabolic perturbations in aging female rats.
2010 Jun 7
Epac2: a sulfonylurea receptor?
2012 Feb
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).
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:52:33 UTC 2023
Edited
by admin
on Wed Jul 05 22:52:33 UTC 2023
Record UNII
WTM2C3IL2X
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
NDF-RT N0000008054
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
WHO-ATC A10BB02
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
NDF-RT N0000008054
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
LIVERTOX 197
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
NCI_THESAURUS C97936
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
NDF-RT N0000175608
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
NDF-RT N0000008054
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID9020322
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
NCI_THESAURUS
C47447
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
IUPHAR
6801
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
LACTMED
Chlorpropamide
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
CAS
94-20-2
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
WIKIPEDIA
CHLORPROPAMIDE
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
RXCUI
2404
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY RxNorm
CHEBI
3650
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
DRUG BANK
DB00672
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
PUBCHEM
2727
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
INN
790
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
NSC
626720
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
RS_ITEM_NUM
1126009
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL498
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
SMS_ID
100000081875
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
NSC
44634
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
FDA UNII
WTM2C3IL2X
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
202-314-5
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
MERCK INDEX
M3462
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY Merck Index
EVMPD
SUB06209MIG
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
DRUG CENTRAL
622
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
HSDB
2051
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
MESH
D002747
Created by admin on Wed Jul 05 22:52:33 UTC 2023 , Edited by admin on Wed Jul 05 22:52:33 UTC 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC