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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.04 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIABINESE

Cmax

ValueDoseCo-administeredAnalytePopulation
28.5 μg/mL
250 mg single, oral
CHLORPROPAMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
545 μg × h/mL
250 mg single, oral
CHLORPROPAMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
33.1 h
250 mg single, oral
CHLORPROPAMIDE plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
WTM2C3IL2X
Record Status Validated (UNII)
Record Version