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Medication for urinary incontinence
Pharmaceutical compound
Darifenacin Trade names Enablex, Emselex AHFS /Drugs.com Monograph MedlinePlus a605039 Pregnancy Routes of By mouth ATC code Legal status
AU :S4 (Prescription only)UK :POM (Prescription only)US :℞-only EU :
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%)
(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 InfoCard 100.118.382 Formula C 28 H 30 N 2 O 2 Molar mass −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
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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] Novartis . In 2010, the US rights were sold to Warner Chilcott for US$400 million .
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]
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 [ edit ] 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] 3 receptor translates into any clinical advantage when treating symptoms of overactive bladder syndrome.[ 4] 3 receptor, darifenacin is also said to antagonize the other four muscarinic acetylcholine receptors.[ 7]
^ 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 . ^ 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 . ^ 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 . ^ a b "Enablex- darifenacin tablet, extended release" . DailyMed . 24 September 2016. Retrieved 22 October 2020 .^ American Urological Association (AUA) Guideline. Diagnosis and Treatment of Overactive Bladder in Adults: AUA/SUFA guideline 2012
^ 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 . ^ 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 .
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists Antagonists
3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol )Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g., brompheniramine , buclizine , captodiame , chlorphenamine (chlorpheniramine) , cinnarizine , clemastine , cyproheptadine , dimenhydrinate , dimetindene , diphenhydramine , doxylamine , meclizine , mequitazine , perlapine , phenindamine , pheniramine , phenyltoloxamine , promethazine , propiomazine , triprolidine )AQ-RA 741 Atropine Atropine methonitrate Atypical antipsychotics (e.g., clozapine , fluperlapine , olanzapine (+fluoxetine ), rilapine , quetiapine , tenilapine , zotepine )Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine Bevonium BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol , +indacaterol , +neostigmine )Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide (+salbutamol )Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g., femoxetine , paroxetine )Telenzepine Terodiline Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g., amitriptyline (+perphenazine ), amitriptylinoxide , butriptyline , cidoxepin , clomipramine , desipramine , desmethyldesipramine , dibenzepin , dosulepin (dothiepin) , doxepin , imipramine , lofepramine , nitroxazepine , northiaden (desmethyldosulepin) , nortriptyline , protriptyline , quinupramine , trimipramine )Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Trospium chloride Typical antipsychotics (e.g., chlorpromazine , chlorprothixene , cyamemazine (cyamepromazine) , loxapine , mesoridazine , thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline Zamifenacin
Precursors (and prodrugs )
Calcium
VDCCs Tooltip Voltage-dependent calcium channels
Potassium
VGKCs Tooltip Voltage-gated potassium channels
IRKs Tooltip Inwardly rectifying potassium channel
KCa Tooltip Calcium-activated potassium channel
K2Ps Tooltip Tandem pore domain potassium channel
Sodium
VGSCs Tooltip Voltage-gated sodium channels
ENaC Tooltip Epithelial sodium channel
ASICs Tooltip Acid-sensing ion channel
Chloride
CaCCs Tooltip Calcium-activated chloride channel
CFTR Tooltip Cystic fibrosis transmembrane conductance regulator
Unsorted
Others
TRPs Tooltip Transient receptor potential channels LGICs Tooltip Ligand gated ion channels
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