Darifenacin

Darifenacin

Clinical data
Trade names	Enablex, Emselex
AHFS/Drugs.com	Monograph
MedlinePlus	a605039
Pregnancy category	AU: B3
Routes of administration	By mouth
ATC code	G04BD10 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only EU: Rx-only
Pharmacokinetic data
Bioavailability	15 to 19% (dose-dependent)
Protein binding	98%
Metabolism	Liver (CYP2D6- and CYP3A4-mediated)
Elimination half-life	13 to 19 hours
Excretion	Kidney (60%) and biliary (40%)
Identifiers
IUPAC name (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl] pyrrolidin-3-yl] -2,2-diphenyl-acetamide
CAS Number	133099-04-4 Y
PubChem CID	444031
IUPHAR/BPS	321
DrugBank	DB00496 Y
ChemSpider	392054 Y
UNII	APG9819VLM
KEGG	D03654 N as salt: D01699 N
ChEBI	CHEBI:391960 Y
ChEMBL	ChEMBL1346 Y
CompTox Dashboard (EPA)	DTXSID2048290
ECHA InfoCard	100.118.382
Chemical and physical data
Formula	C28H30N2O2
Molar mass	426.560 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(N)C(c1ccccc1)(c2ccccc2)[C@H]3CN(CC3)CCc5cc4c(OCC4)cc5
InChI InChI=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 Y Key:HXGBXQDTNZMWGS-RUZDIDTESA-N Y
NY (what is this?)  (verify)

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. 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.

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 likely associated with benign prostatic hypertrophy.

Mechanism of action

Darifenacin works by blocking the M₃muscarinic acetylcholine receptor, which is primarily responsible for bladder muscle contractions. It thereby decreases the urgency to urinate. It is not known whether this selectivity for the M₃ receptor translates into any clinical advantage when treating symptoms of overactive bladder syndrome.

External links

• "Darifenacin". Drug Information Portal. U.S. National Library of Medicine.
• "Darifenacin hydrobromide". Drug Information Portal. U.S. National Library of Medicine.