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Darifenacin

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Darifenacin
Clinical data
Trade namesEnablex, Emselex
AHFS/Drugs.comMonograph
MedlinePlusa605039
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability15 to 19% (dose-dependent)
Protein binding98%
MetabolismLiver (CYP2D6- and CYP3A4-mediated)
Elimination half-life13 to 19 hours
ExcretionKidney (60%) and biliary (40%)
Identifiers
  • (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl] pyrrolidin-3-yl] -2,2-diphenyl-acetamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.118.382 Edit this at Wikidata
Chemical and physical data
FormulaC28H30N2O2
Molar mass426.560 g·mol−1
3D model (JSmol)
  • O=C(N)C(c1ccccc1)(c2ccccc2)[C@H]3CN(CC3)CCc5cc4c(OCC4)cc5
  • 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 checkY
  • Key:HXGBXQDTNZMWGS-RUZDIDTESA-N checkY
 ☒NcheckY (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.[1][2][3] 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

[edit]

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.[4]

Medical uses

[edit]

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. [5]

Mechanism of action

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Darifenacin works by blocking the M3 muscarinic acetylcholine receptor, which is primarily responsible for bladder muscle contractions. It thereby decreases the urgency to urinate.[6] It is not known whether this selectivity for the M3 receptor translates into any clinical advantage when treating symptoms of overactive bladder syndrome.[4] Although it is said to be selective for the M3 receptor, darifenacin is also said to antagonize the other four muscarinic acetylcholine receptors.[7]

References

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  1. ^ Croom KF, Keating GM (2004). "Darifenacin: in the treatment of overactive bladder". Drugs & Aging. 21 (13): 885–92, discussion 893–4. doi:10.2165/00002512-200421130-00005. PMID 15493952. S2CID 41549419.
  2. ^ Parsons M, Robinson D, Cardozo L (July 2005). "Darifenacin in the treatment of overactive bladder". International Journal of Clinical Practice. 59 (7): 831–8. doi:10.1111/j.1368-5031.2005.00585.x. PMID 15963212. S2CID 39061659.
  3. ^ Chughtai B, Levin R, De E (2008). "Choice of antimuscarinic agents for overactive bladder in the older patient: focus on darifenacin". Clinical Interventions in Aging. 3 (3): 503–9. doi:10.2147/cia.s3414. PMC 2682382. PMID 18982920.
  4. ^ a b "Enablex- darifenacin tablet, extended release". DailyMed. 24 September 2016. Retrieved 22 October 2020.
  5. ^ American Urological Association (AUA) Guideline. Diagnosis and Treatment of Overactive Bladder in Adults: AUA/SUFA guideline 2012
  6. ^ Chapple CR (November 2004). "Darifenacin: a novel M3 muscarinic selective receptor antagonist for the treatment of overactive bladder". Expert Opinion on Investigational Drugs. 13 (11): 1493–500. doi:10.1517/13543784.13.11.1493. PMID 15500396. S2CID 19259076.
  7. ^ Lavrador M, Cabral AC, Veríssimo MT, Fernandez-Llimos F, Figueiredo IV, Castel-Branco MM (January 2023). "A Universal Pharmacological-Based List of Drugs with Anticholinergic Activity". Pharmaceutics. 15 (1): 230. doi:10.3390/pharmaceutics15010230. PMC 9863833. PMID 36678858.
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