Darifenacin (CHEM002513)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-07-30 17:58:49 UTC
Update Date2016-11-09 01:08:52 UTC
Accession NumberCHEM002513
Identification
Common NameDarifenacin
ClassSmall Molecule
DescriptionDarifenacin (Enablex™, Novartis) is a medication used to treat urinary incontinence. 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 should not be used in people with urinary retention. It is not known whether this selectivity for the M3 receptor translates into any clinical advantage when treating symptoms of overactive bladder syndrome.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Antispasmodic Agent
  • Drug
  • Ether
  • Metabolite
  • Muscarinic Antagonist
  • Organic Compound
  • Synthetic Compound
  • Urinary Antispasmodic
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-1-(2-(2,3-Dihydro-5-benzofuranyl)ethyl)-alpha,alpha-diphenyl-3-pyrrolidineacetamideChEBI
(S)-1-(2-(2,3-Dihydro-5-benzofuranyl)ethyl)-a,a-diphenyl-3-pyrrolidineacetamideGenerator
(S)-1-(2-(2,3-Dihydro-5-benzofuranyl)ethyl)-α,α-diphenyl-3-pyrrolidineacetamideGenerator
EnablexHMDB
Darifenacin hydrochlorideHMDB
DarifenicinHMDB
Darifenacin hydrobromideHMDB
EmselexHMDB
DarifenacineHMDB
Chemical FormulaC28H30N2O2
Average Molecular Mass426.550 g/mol
Monoisotopic Mass426.231 g/mol
CAS Registry Number133099-04-4
IUPAC Name2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide
Traditional Namedarifenacin
SMILESNC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=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
InChI KeyHXGBXQDTNZMWGS-RUZDIDTESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylacetamide
  • Phenethylamine
  • Coumaran
  • Alkyl aryl ether
  • Aralkylamine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Primary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility2.98e-04 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.0003 g/LALOGPS
logP4.35ALOGPS
logP4.54ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)16.21ChemAxon
pKa (Strongest Basic)10.11ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.56 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity128.37 m³·mol⁻¹ChemAxon
Polarizability48.54 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lv-2491000000-40c43db64189724fe0c2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0101900000-1979d23256753a983573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gj-0756900000-6e69c78743e94527add2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxs-2910000000-ec1acf0e02b7c0a392f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-e8c519b1d7f130de607aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4285900000-73144c3d58ba99d76581Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9030000000-5dfb7a1ae0753d3d4c11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005c-4005900000-8a58ca84e09117fd29e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9004100000-2c811675031a777fbc67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9212000000-514c545cfeaf92ef3a8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0002900000-3905ca525d1dcc4e15f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0104900000-359dc4da59d626f0edf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0932000000-13b487199d725fb1e357Spectrum
Toxicity Profile
Route of ExposureThe mean oral bioavailability at steady state is estimated to be 15% and 19% for 7.5 mg and 15 mg tablets, respectively.
Mechanism of ToxicityDarifenacin 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.
MetabolismHepatic. 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.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency and frequency.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsOverdosage can potentially result in severe central anticholinergic effects.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00496
HMDB IDHMDB0014639
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDarifenacin
Chemspider ID392054
ChEBI ID391960
PubChem Compound ID444031
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Valeriano Merli, Augusto Canavesi, Paola Daverio, “Processes for preparing darifenacin hydrobromide.” U.S. Patent US20070197631, issued August 23, 2007.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11831911
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14616424