Structure via PubChem · Public domain (PubChem)
chlorpropamide
Sign in to saveAlso known as Diabenese®, Glucamide®, n-propyl-N'-p-chlorophenylsulfonylcarbamide, 1-(p-chlorophenylsulfonyl)-3-propylurea, N-(4-chlorophenylsulfonyl)-N'-propylurea, 1-propyl-3-(p-chlorobenzenesulfonyl)urea, 1-(p-chlorobenzenesulfonyl)-3-propylurea, N-(p-chlorobenzenesulfonyl)-N'-propylurea
Chlorpropamide is a diabetes medication, belonging to the sulfonylurea class of organic compounds. It is used to treat diabetes mellitus type 2. It is a long-acting first-generation sulfonylurea.
Chemical data
- Formula
- C10H13ClN2O3S
- Molecular weight
- 276.74 g/mol
- IUPAC name
- 1-(4-chlorophenyl)sulfonyl-3-propylurea
- SMILES
- CCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)Cl
- InChIKey
- RKWGIWYCVPQPMF-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 83.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1958
- Admin. routes
- oral
- Indications
- diabetes mellitus, type 2 diabetes mellitus
via ChEMBL · EBI
Research
2,112 papers- Chlorpropamide antidiuresis.The New England journal of medicine · 1971
- Chlorpropamide hyponatremia.Journal of the Medical Association of Thailand = Chotmaihet thangphaet · 1974
- Chlorpropamide hyponatremia.The New England journal of medicine · 1972
- Chlorpropamide toxicity.The American journal of medicine · 1988
- Chlorpropamide-induced hyponatremia.The Journal of clinical endocrinology and metabolism · 1976
via PubMed
Wikidata facts
- Subclass of
- sulfonylurea
- Mass
- 276.033541
- Has use
- medication
Show 9 more facts
- chemical formula
- C₁₀H₁₃ClN₂O₃S
- medical condition treated
- type 2 diabetes
- isomeric SMILES
- CCC/N=C(/NS(=O)(=O)C1=CC=C(C=C1)Cl)\O
- World Health Organisation international non-proprietary name
- chlorpropamide
- canonical SMILES
- CCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)Cl
- defined daily dose
- 0.375
- subject has role
- anti-diabetic medication
- stylized name
- chlorproPAMIDE
- Commons category
- Chlorpropamide
Sources (8)
via Wikidata · CC0
~3 min read
Encyclopedic overview
8 sectionsContents
- Mechanism of action
- Pharmacokinetics
- Cautions and contraindications
- Other side effects
- Chemical properties
- Solubility
- See also
- References
Chlorpropamide is a diabetes medication, belonging to the sulfonylurea class of organic compounds. It is used to treat diabetes mellitus type 2. It is a long-acting first-generation sulfonylurea.
==Mechanism of action== Like other sulfonylureas, chlorpropamide acts to increase the secretion of insulin, so it is only effective in patients who have some pancreatic beta cell function. It can cause relatively long episodes of hypoglycemia; this is one reason why shorter-acting sulfonylureas such as gliclazide or tolbutamide are used instead. The risk of hypoglycemia makes this drug a poor choice for the elderly and patients with mild to moderate hepatic and renal impairment. Chlorpropamide is also used in partial central diabetes insipidus.
Excerpted from Wikipedia’s “chlorpropamide” article, available under the CC BY-SA 4.0 licence.