Chlorpropamide

Source: Wikipedia, the free encyclopedia.
Not to be confused with Chlorpromazine.
Chlorpropamide
Clinical data
Trade namesDiabinese
AHFS/Drugs.comMonograph
MedlinePlusa682479
License data
Pregnancy
category
  • AU: C
Routes of
administration		Oral
ATC code
Legal status
Legal status
Renal
(glomerular filtration → reabsorption → tubular secretion)
Identifiers
  • 4-chloro-N-(propylcarbamoyl)benzenesulfonamide
JSmol)
Melting point126 to 130 °C (259 to 266 °F)
  • O=S(=O)(c1ccc(Cl)cc1)NC(=O)NCCC
  • 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) checkY
  • Key:RKWGIWYCVPQPMF-UHFFFAOYSA-N checkY
  (verify)

Chlorpropamide is an antidiabetic

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.[1]

Pharmacokinetics

secreted into the tubular lumen.[1]

Cautions and contraindications

Further information: Sulfonylurea § Side-effects and cautions

Chlorpropamide and other sulfonylureas encourage weight gain, so they are generally not favored for use in very obese patients. Metformin (Glucophage) is considered a better drug for these patients. Sulfonylureas should be used with caution or generally avoided in patients with hepatic and renal impairment, patients with porphyria, patients who are breastfeeding, patients with ketoacidosis, and elderly patients.[1][2] Chlorpropamide, while effective in the treatment of diabetics in patients of Chinese descent, should never be used in people of Mongolian descent.[citation needed]

Other side effects

The most common side effects are skin related, such as

antidiuretic hormone (ADH), which can lead to hyponatremia.[1] It also markedly raises the serum level of alkaline phosphatase.[citation needed
]

Chemical properties

Chlorpropamide is a white crystalline powder with no characteristic taste or smell. It exhibits

polymorphism. Its acid dissociation constant pKa is 5.0 at 20 °C.[1]

Solubility

Solvent Solubility[1]
Water, pH 6 1:450
Water, pH 7.3 insoluble
Acetone 1:5
Dichlormethane 1:9
Ethanol 1:12
Diethylether 1:200

See also

References

  1. ^
    ISBN 978-3-7741-9846-3
    .
  2. ^ a b "Chlorpropamide". Drugs.com. Archived from the original on 2021-03-04. Retrieved 2018-01-23.
  3. PMID 13893349
    .