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QuickView for Darifenacin (compound)

Summary
General Info

PubChem

PubChem Compound 444030

PubChem Compound 444030

Name:	darifenacin
PubChem Compound ID:	444030
Molecular formula:	C₂₈H₃₁BrN₂O₂
Molecular weight:	507.462 g/mol
Synonyms:	Darifenacin hydrobromide (JAN/USAN); UK-88525; UK-88525-04; Darifenacin hydrobromide; D01699; 133099-07-7; Emselex; Enablex; Enablex (TN)

DrugBank

Identification

Name:	darifenacin
Name (isomeric):	DB00496
Drug Type:	small molecule
Brand:	Enablex, Emselex
Category:	Muscarinic Antagonists, Urinary antispasmodics
CAS number:	133099-04-4

Pharmacology

Indication:	For the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency and frequency.
Pharmacology:	Darifenacin is a competitive muscarinic receptor antagonist. In vitro studies using human recombinant muscarinic receptor subtypes show that darifenacin has greater affinity for the M3 receptor than for the other known muscarinic receptors (9 and 12-fold greater affinity for M3 compared to M1 and M5, respectively, and 59-fold greater affinit... show more » Darifenacin is a competitive muscarinic receptor antagonist. In vitro studies using human recombinant muscarinic receptor subtypes show that darifenacin has greater affinity for the M3 receptor than for the other known muscarinic receptors (9 and 12-fold greater affinity for M3 compared to M1 and M5, respectively, and 59-fold greater affinity for M3 compared to both M2 and M4). Muscarinic receptors play an important role in several major cholinergically mediated functions, including contractions of the urinary bladder smooth muscle and stimulation of salivary secretion. Adverse drug effects such as dry mouth, constipation and abnormal vision may be mediated through effects on M3 receptors in these organs. show less «
Mechanism of Action:	Darifenacin selectively antagonizes the muscarinic M3 receptor. M3 receptors are involved in contraction of human bladder and gastrointestinal smooth muscle, saliva production, and iris sphincter function.
Absorption:	The mean oral bioavailability at steady state is estimated to be 15% and 19% for 7.5 mg and 15 mg tablets, respectively.
Protein binding:	Darifenacin is approximately 98% bound to plasma proteins (primarily to alpha-1-acid-glycoprotein).
Biotransformation:	Hepatic. Primarily mediated by the cytochrome P450 enzymes CYP2D6 and CYP3A4.
Half Life:	The elimination half-life of darifenacin following chronic dosing is approximately 13-19 hours.
Clearance:	40 L/h [extensive metabolizers] 32 L/h [poor metabolizers]
Toxicity:	Overdosage can potentially result in severe central anticholinergic effects.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Clarithromycin	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Tacrine	The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Darifenacin, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Ketoconazole	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Telithromycin	Telithromycin may reduce clearance of Darifenacin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Darifenacin if Telithromycin is initiated, discontinued or dose changed.
Nefazodone	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism

Clarithromycin	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Tacrine	The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Darifenacin, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Ketoconazole	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Telithromycin	Telithromycin may reduce clearance of Darifenacin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Darifenacin if Telithromycin is initiated, discontinued or dose changed.
Nefazodone	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Tamoxifen	Darifenacin may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
Ritonavir	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Tamsulosin	Darifenacin, a CYP2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Darifenacin is initiated, discontinued, or dose changed.
Galantamine	Possible antagonism of action
Nelfinavir	Nelfinavir, a strong CYP3A4 inhibitor, may decrease the metabolism of darifenacin/solifenacin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of darifenacin if nelfinavir is initiated, discontinued or dose changed.
Itraconazole	This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Triprolidine	Triprolidine and Darifenacin, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Donepezil	Possible antagonism of action
Tramadol	Darifenacin may decrease the effect of Tramadol by decreasing active metabolite production.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of darifenacin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of darifenacin if voriconazole is initiated, discontinued or dose changed.
Trospium	Trospium and Darifenacin, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Rivastigmine	Possible antagonism of action

Targets

Muscarinic acetylcholine receptor M3

Muscarinic acetylcholine receptor M1

Muscarinic acetylcholine receptor M2

Muscarinic acetylcholine receptor M4

Muscarinic acetylcholine receptor M5

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2D6