# Chlorpropamide
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Chlorpropamide
> Markdown URL: https://mediated.wiki/source/Chlorpropamide.md
> Source: https://en.wikipedia.org/wiki/Chlorpropamide
> Source revision: 1329246521
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{Short description|Chemical compound}}
{{distinguish|Chlorpromazine}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 457796377
| IUPAC_name = 4-chloro-''N''-(propylcarbamoyl)benzenesulfonamide
| image = Chlorpropamide.svg
| image_class = skin-invert-image
| image2 = Chlorpropamide ball-and-stick.png
| image_class2 = bg-transparent
| tradename = Diabinese
| Drugs.com = {{drugs.com|monograph|chlorpropamide}}
| MedlinePlus = a682479
| licence_US = Chlorpropamide
| pregnancy_AU = C
| pregnancy_US = C
| legal_AU = S4
| legal_CA = Rx-only
| legal_UK = POM
| legal_US = Rx-only
| routes_of_administration = Oral
| bioavailability = >90%
| protein_bound = 90%
| metabolism = <1%
| excretion = [Renal](/source/Renal) (glomerular filtration → reabsorption → tubular secretion)
| elimination_half-life = 36 hours
| IUPHAR_ligand = 6801
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 94-20-2
| ATC_prefix = A10
| ATC_suffix = BB02
| PubChem = 2727
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00672
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2626
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = WTM2C3IL2X
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00271
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 3650
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 498
| C=10 | H=13 | Cl=1 | N=2 | O=3 | S=1
| smiles = O=S(=O)(c1ccc(Cl)cc1)NC(=O)NCCC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RKWGIWYCVPQPMF-UHFFFAOYSA-N
| melting_point = 126
| melting_high = 130
}}
'''Chlorpropamide''' is a [diabetes medication](/source/diabetes_medication), belonging to the [sulfonylurea](/source/sulfonylurea) class of organic compounds. It is used to treat [diabetes mellitus type 2](/source/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](/source/insulin), so it is only effective in patients who have some [pancreatic](/source/pancreas) [beta cell](/source/beta_cell) function. It can cause relatively long episodes of [hypoglycemia](/source/hypoglycemia); this is one reason why shorter-acting sulfonylureas such as [gliclazide](/source/gliclazide) or [tolbutamide](/source/tolbutamide) are used instead. The risk of hypoglycemia makes this drug a poor choice for the [elderly](/source/Old_age) and patients with mild to moderate [hepatic](/source/liver) and [renal](/source/kidney) impairment. Chlorpropamide is also used in partial [central diabetes insipidus](/source/central_diabetes_insipidus).[{{cite book | title = Arzneistoff-Profile | veditors = Dinnendahl V, Fricke U | publisher = Govi Pharmazeutischer Verlag | location = Eschborn, Germany | date = 2010 | edition = 23 | volume = 4 | isbn = 978-3-7741-9846-3 | language = de }}]
==Pharmacokinetics==
[Maximal plasma concentrations](/source/Cmax_(pharmacology)) are reached 3 to 5 hours after quick and nearly complete (>90%) resorption from the gut. [plasma](/source/Blood_plasma) [half life](/source/half_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 two [albumin](/source/albumin) binding sites exist. More than 99% of chlorpropamide are excreted unchanged via the kidneys. It is first filtrated in the [glomeruli](/source/Glomerulus_(kidney)), then reabsorbed, and finally [secreted into the tubular lumen](/source/tubular_secretion).[{{cite web | work = Drugs.com | url = https://www.drugs.com/monograph/chlorpropamide.html | title = Chlorpropamide | access-date = 2018-01-23 | archive-date = 2021-03-04 | archive-url = https://web.archive.org/web/20210304101757/https://www.drugs.com/monograph/chlorpropamide.html | url-status = dead }}]
===Other side effects===
The most common side effects are skin related, such as [rashes](/source/rashes), [photoallergy](/source/photoallergy) and (in rare cases) [Stevens–Johnson syndrome](/source/Stevens%E2%80%93Johnson_syndrome).[{{cite journal | vauthors = Fitzgerald MG, Gaddie R, Malins JM, O'Sullivan DG | title = Alcohol sensitivity in diabetics receiving chlorpropromide | journal = Diabetes | volume = 11 | pages = 40–3 | date = 1962 | pmid = 13893349 }}] In very high doses it can increase secretion of [antidiuretic hormone](/source/antidiuretic_hormone) (ADH), which can lead to [hyponatremia](/source/hyponatremia).