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
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)
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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68002747
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
Sources: https://patents.google.com/patent/GB853555A
Curator's Comment: # Pfizer Inc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2096972 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22209866 |
3.04 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DIABINESE Approved UseChlorpropamide tablets are indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Launch Date1958 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
28.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5053812/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
545 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5053812/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5053812/ |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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 victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major [Km 249.6 uM] | ||||
major [Km 584.9 uM] | ||||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
minor |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Chlorpropamide-induced immune hemolytic anemia. | 1970 Oct 22 |
|
Severe hypoglycaemic shock caused by chlorpropamide. (Case report). | 1971 Jan |
|
Postoperative hypoglycaemic coma associated with chlorpropamide. | 1975 Aug |
|
Chlorpropamide-alcohol flushing: a dominantly inherited trait associated with diabetes. | 1978 Dec 2 |
|
Tolazamide-induced cholestasis. | 1980 Aug |
|
Hypoglycemic coma, jaundice, and pure RBC aplasia following chlorpropamide therapy. | 1980 May |
|
Chlorpropamide-induced pure RBC aplasia. | 1980 May |
|
A case of chronic liver disease due to tolazamide. | 1985 Jul |
|
Chlorpropamide induced syndrome of inappropriate secretion of antidiuretic hormone. | 1991 Aug |
|
Chlorpropamide or chlorpromazine? | 1991 Jan 15 |
|
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 |
|
The structure and function of the ATP-sensitive K+ channel in insulin-secreting pancreatic beta-cells. | 1999 Apr |
|
[Hepatotoxic reaction associated with metformin and chlorpropamide treatment]. | 1999 Feb |
|
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro. | 2003 Aug |
|
Functional recovery after surgical resection of low grade gliomas in eloquent brain: hypothesis of brain compensation. | 2003 Jul |
|
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 |
|
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 |
|
Comprehensive in silico prediction and analysis of chlamydial outer membrane proteins reflects evolution and life style of the Chlamydiae. | 2009 Dec 29 |
|
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 |
|
Ameliorative effects of Cnidoscolus aconitifolius on alloxan toxicity in Wistar rats. | 2010 Sep |
|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22209866
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
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Record UNII |
WTM2C3IL2X
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Validated (UNII)
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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