View source for Darifenacin

{{Short description|Medication for urinary incontinence}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460773728
| image = Darifenacin.svg
| alt = 
| image2 = Darifenacin-hydrobromide-from-xtal-2009-CM-3D-balls.png
| alt2 = 

<!--Clinical data-->
| tradename = Enablex, Emselex
| Drugs.com = {{drugs.com|monograph|darifenacin-hydrobromide}}
| MedlinePlus = a605039
| pregnancy_AU = B3
| pregnancy_US = C
| ATC_prefix = G04
| ATC_suffix = BD10
| ATC_supplemental =  

| legal_AU = S4
| legal_UK = POM
| legal_US = Rx-only
| legal_EU = Rx-only
| routes_of_administration = [[Oral administration|By mouth]]

<!--Pharmacokinetic data-->
| bioavailability = 15 to 19% (dose-dependent)
| protein_bound = 98%
| metabolism = [[Liver]] ([[CYP2D6]]- and [[CYP3A4]]-mediated)
| elimination_half-life = 13 to 19 hours
| excretion = [[Kidney]] (60%) and biliary (40%)

<!--Identifiers-->
| index2_label = as salt
| IUPHAR_ligand = 321
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 133099-04-4
| PubChem = 444031
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00496
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 392054
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = APG9819VLM
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D03654
| KEGG2_Ref = {{keggcite|changed|kegg}}
| KEGG2 = D01699
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 391960
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1346

<!--Chemical data-->
| IUPAC_name = (''S'')-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl] pyrrolidin-3-yl] -2,2-diphenyl-acetamide
| C=28 | H=30 | N=2 | O=2
| smiles = O=C(N)C(c1ccccc1)(c2ccccc2)[C@H]3CN(CC3)CCc5cc4c(OCC4)cc5
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C28H30N2O2/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26/h1-12,19,25H,13-18,20H2,(H2,29,31)/t25-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HXGBXQDTNZMWGS-RUZDIDTESA-N
}}

'''Darifenacin''' (trade name '''Enablex''' in United States and Canada, '''Emselex''' in the European Union) is a [[medication]] used to treat [[urinary incontinence]] due to an [[overactive bladder]].<ref name="Croom_2004">{{cite journal | vauthors = Croom KF, Keating GM | title = Darifenacin: in the treatment of overactive bladder | journal = Drugs & Aging | volume = 21 | issue = 13 | pages = 885–92; discussion 893–4 | date = 2004 | pmid = 15493952 | doi = 10.2165/00002512-200421130-00005 | s2cid = 41549419 }}</ref><ref name="Parsons_2005">{{cite journal | vauthors = Parsons M, Robinson D, Cardozo L | title = Darifenacin in the treatment of overactive bladder | journal = International Journal of Clinical Practice | volume = 59 | issue = 7 | pages = 831–8 | date = July 2005 | pmid = 15963212 | doi = 10.1111/j.1368-5031.2005.00585.x | s2cid = 39061659 | doi-access = free }}</ref><ref name="Chughtai_2008">{{cite journal | vauthors = Chughtai B, Levin R, De E | title = Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin | journal = Clinical Interventions in Aging | volume = 3 | issue = 3 | pages = 503–9 | date = 2008 | pmid = 18982920 | pmc = 2682382 | doi = 10.2147/cia.s3414 | doi-access = free }}</ref> It was discovered by scientists at the Pfizer research site in Sandwich, UK under the identifier UK-88,525 and used to be marketed by [[Novartis]]. In 2010, the US rights were sold to [[Warner Chilcott]] for {{US$|400 million}}.

== Adverse effects ==
Darifenacin should not be used in people with [[urinary retention]]. [[Anticholinergic agents]], such as darifenacin, may also produce constipation and blurred vision. [[Heat prostration]] (due to decreased sweating) can occur when anticholinergics such as darifenacin are used in a hot environment.<ref name="Enablex FDA label">{{cite web | title=Enablex- darifenacin tablet, extended release | website=DailyMed | date=24 September 2016 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a712f252-16d9-47df-b2bf-6794228f3a88 | access-date=22 October 2020}}</ref>

== Medical uses ==
Darifenacin is indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and frequency in adults. It may also be recommended with an [[alpha blocker]] to help provide symptomatic benefit for overactive bladder and obstructive symptoms such as those likely associated with [[benign prostatic hyperplasia]]. <ref>American Urological Association (AUA) Guideline. Diagnosis and Treatment of Overactive Bladder in Adults: AUA/SUFA guideline 2012</ref>

== Mechanism of action ==
Darifenacin works by blocking the M<sub>3</sub> [[muscarinic acetylcholine receptor]], which is primarily responsible for [[urinary bladder|bladder]] [[muscle contraction]]s.  It thereby decreases the urgency to [[urinate]].<ref name="Chapple_2004">{{cite journal | vauthors = Chapple CR | title = Darifenacin: a novel M3 muscarinic selective receptor antagonist for the treatment of overactive bladder | journal = Expert Opinion on Investigational Drugs | volume = 13 | issue = 11 | pages = 1493–500 | date = November 2004 | pmid = 15500396 | doi = 10.1517/13543784.13.11.1493 | s2cid = 19259076 }}</ref> It is not known whether this selectivity for the M<sub>3</sub> receptor translates into any clinical advantage when treating symptoms of [[overactive bladder]] syndrome.<ref name="Enablex FDA label" />

== References ==
{{Reflist}}

== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/darifenacin | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Darifenacin }}
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/darifenacin%20hydrobromide | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Darifenacin hydrobromide }}

{{Urologicals}}
{{Muscarinic acetylcholine receptor modulators}}
{{Ion channel modulators}}
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[[Category:5-Benzofuranethanamines]]
[[Category:Benzhydryl compounds]]
[[Category:Carboxamides]]
[[Category:CYP2D6 inhibitors]]
[[Category:Drugs developed by AbbVie]]
[[Category:Drugs developed by Novartis]]
[[Category:HERG blocker]]
[[Category:M1 receptor antagonists]]
[[Category:M2 receptor antagonists]]
[[Category:M3 receptor antagonists]]
[[Category:M4 receptor antagonists]]
[[Category:M5 receptor antagonists]]
[[Category:Pyrrolidines]]