Darifenacin

Darifenacin
Names
Trade namesEnablex, Emselex, others
IUPAC name
  • (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl] pyrrolidin-3-yl] -2,2-diphenyl-acetamide
Clinical data
Drug classAnticholinergic[1]
Main usesOveractive bladder[2]
Side effectsDry mouth, constipation[2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: B3
  • US: C (Risk not ruled out)
    Routes of
    use    		By mouth
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa605039
    Legal
    Legal status
    • AU: S4 (Prescription only)
    • UK: POM (Prescription only)
    • US: ℞-only
    • EU: Rx-only
    Pharmacokinetics
    Bioavailability15 to 19% (dose-dependent)
    Protein binding98%
    MetabolismLiver (CYP2D6- and CYP3A4-mediated)
    Elimination half-life13 to 19 hours
    ExcretionKidney (60%) and biliary (40%)
    Chemical and physical data
    FormulaC28H30N2O2
    Molar mass426.560 g·mol−1
    3D model (JSmol)
    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 checkY
    • Key:HXGBXQDTNZMWGS-RUZDIDTESA-N checkY

    Darifenacin, sold under the trade name Enablex among others, is a medication used to treat overactive bladder.[2] It is taken once per day by mouth.[2] Benefits are generally seen within 2 weeks.[2]

    Common side effects include dry mouth and constipation.[2] Other side effects may include cough, bladder pain, blurry vision, urinary retention, shortness of breath, sexual dysfunction, and high blood pressure.[2][3] Use is not recommended during pregnancy.[3] It is an anticholinergic which helps the bladder relax.[1]

    Darifenacin was approved for medical use in the United States and Europe in 2004.[2][1] It is available as a generic medication.[4] In the United States it costs about 37 USD per month as of 2021.[4] This amount in the United Kingdom costs the NHS about £25.[3]

    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. [5]

    Dosage

    The typically dose is 7.5 to 15 mg once per day.[2]

    Side 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.[6]

    Mechanism of action

    Darifenacin works by blocking the M3 muscarinic 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.[6]

    History

    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.

    References

    1. 1 2 3 "Emselex". Archived from the original on 10 January 2021. Retrieved 21 July 2021.
    2. 1 2 3 4 5 6 7 8 9 "Darifenacin Monograph for Professionals". Drugs.com. Archived from the original on 18 January 2021. Retrieved 21 July 2021.
    3. 1 2 3 BNF (80 ed.). BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 821. ISBN 978-0-85711-369-6.{{cite book}}: CS1 maint: date format (link)
    4. 1 2 "Darifenacin ER Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 4 July 2016. Retrieved 21 July 2021.
    5. ↑ American Urological Association (AUA) Guideline. Diagnosis and Treatment of Overactive Bladder in Adults: AUA/SUFA guideline 2012
    6. 1 2 "Enablex- darifenacin tablet, extended release". DailyMed. 24 September 2016. Archived from the original on 26 October 2020. Retrieved 22 October 2020.
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