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| Clinical data | |
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| Trade names | Diabinese |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682479 |
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| Routes of administration | Oral |
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| Pharmacokinetic data | |
| Bioavailability | >90% |
| Protein binding | 90% |
| Metabolism | <1% |
| Eliminationhalf-life | 36 hours |
| Excretion | Renal (glomerular filtration → reabsorption → tubular secretion) |
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| ECHA InfoCard | 100.002.104 |
| Chemical and physical data | |
| Formula | C10H13ClN2O3S |
| Molar mass | 276.74 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 126 to 130 °C (259 to 266 °F) |
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Chlorpropamide is an antidiabeticdrug, belonging to thesulfonylurea class of organic compounds. It is used to treatdiabetes mellitus type 2. It is a long-acting first-generation sulfonylurea.
Like other sulfonylureas, chlorpropamide acts to increase the secretion ofinsulin, so it is only effective in patients who have somepancreaticbeta cell function. It can cause relatively long episodes ofhypoglycemia; this is one reason why shorter-acting sulfonylureas such asgliclazide ortolbutamide are used instead. The risk of hypoglycemia makes this drug a poor choice for theelderly and patients with mild to moderatehepatic andrenal impairment. Chlorpropamide is also used in partialcentral diabetes insipidus.[1]
Maximal plasma concentrations are reached 3 to 5 hours after quick and nearly complete (>90%) resorption from the gut.plasmahalf life is 36 hours; the drug is effective for about 24 hours, longer than other sulfonylureas. A stable plasma level is only reached after three days of continuous application. 90% of the drug are bound to plasma proteins; at least twoalbumin binding sites exist. More than 99% of chlorpropamide are excreted unchanged via the kidneys. It is first filtrated in theglomeruli, then reabsorbed, and finallysecreted into the tubular lumen.[1]
Chlorpropamide and other sulfonylureas encourage weight gain, so they are generally not favored for use in veryobese 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 withporphyria, patients who arebreastfeeding, patients withketoacidosis, and elderly patients.[1][2]
The most common side effects are skin related, such asrashes,photoallergy and (in rare cases)Stevens–Johnson syndrome.[1] Less common side effects of chlorpropamide include gastrointestinal symptoms such asnausea,vomiting, anddiarrhea.[2] It may causefacial flushing after the ingestion ofalcohol.[3] In very high doses it can increase secretion ofantidiuretic hormone (ADH), which can lead tohyponatremia.[1] It also markedly raises the serum level ofalkaline phosphatase.[citation needed]
Chlorpropamide is a white crystalline powder with no characteristic taste or smell. It exhibitspolymorphism. Itsacid dissociation constant pKa is 5.0 at 20 °C.[1]
| 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 |
