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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014639
Secondary Accession Numbers
  • HMDB14639
Metabolite Identification
Common NameDarifenacin
DescriptionDarifenacin, also known as enablex or emselex, 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. Darifenacin is a drug which is used for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency and frequency. Darifenacin is a very strong basic compound (based on its pKa). Darifenacin is a potentially toxic compound.
Structure
Data?1582753202
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 Weight426.55
Monoisotopic Molecular Weight426.230728214
IUPAC Name2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide
Traditional Namedarifenacin
CAS Registry Number133099-04-4
SMILES
NC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
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
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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0003 g/LNot Available
LogP4.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.83931661259
DarkChem[M-H]-195.61331661259
DeepCCS[M+H]+198.24730932474
DeepCCS[M-H]-195.85130932474
DeepCCS[M-2H]-228.73530932474
DeepCCS[M+Na]+204.15930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DarifenacinNC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C14286.0Standard polar33892256
DarifenacinNC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C13585.3Standard non polar33892256
DarifenacinNC(=O)C([C@@H]1CCN(CCC2=CC3=C(OCC3)C=C2)C1)(C1=CC=CC=C1)C1=CC=CC=C13643.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Darifenacin,1TMS,isomer #1C[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C13669.9Semi standard non polar33892256
Darifenacin,1TMS,isomer #1C[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C13317.7Standard non polar33892256
Darifenacin,1TMS,isomer #1C[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C14505.3Standard polar33892256
Darifenacin,2TMS,isomer #1C[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C3694.3Semi standard non polar33892256
Darifenacin,2TMS,isomer #1C[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C3479.4Standard non polar33892256
Darifenacin,2TMS,isomer #1C[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C4331.1Standard polar33892256
Darifenacin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C13891.0Semi standard non polar33892256
Darifenacin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C13572.7Standard non polar33892256
Darifenacin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C14565.2Standard polar33892256
Darifenacin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C(C)(C)C4129.2Semi standard non polar33892256
Darifenacin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C(C)(C)C3877.8Standard non polar33892256
Darifenacin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@@H]1CCN(CCC2=CC=C3OCCC3=C2)C1)[Si](C)(C)C(C)(C)C4368.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Darifenacin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lv-2491000000-40c43db64189724fe0c22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Darifenacin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 10V, Positive-QTOFsplash10-004i-0101900000-1979d23256753a9835732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 20V, Positive-QTOFsplash10-03gj-0756900000-6e69c78743e94527add22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 40V, Positive-QTOFsplash10-0uxs-2910000000-ec1acf0e02b7c0a392f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 10V, Negative-QTOFsplash10-004i-0001900000-e8c519b1d7f130de607a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 20V, Negative-QTOFsplash10-004i-4285900000-73144c3d58ba99d765812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 40V, Negative-QTOFsplash10-0006-9030000000-5dfb7a1ae0753d3d4c112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 10V, Negative-QTOFsplash10-005c-4005900000-8a58ca84e09117fd29e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 20V, Negative-QTOFsplash10-0006-9004100000-2c811675031a777fbc672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 40V, Negative-QTOFsplash10-0006-9212000000-514c545cfeaf92ef3a8e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 10V, Positive-QTOFsplash10-004i-0002900000-3905ca525d1dcc4e15f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 20V, Positive-QTOFsplash10-004i-0104900000-359dc4da59d626f0edf42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Darifenacin 40V, Positive-QTOFsplash10-0002-0932000000-13b487199d725fb1e3572021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00496 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00496 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00496
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID392054
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDarifenacin
METLIN IDNot Available
PubChem Compound444031
PDB IDNot Available
ChEBI ID391960
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Skerjanec A: The clinical pharmacokinetics of darifenacin. Clin Pharmacokinet. 2006;45(4):325-50. [PubMed:16584282 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Skerjanec A: The clinical pharmacokinetics of darifenacin. Clin Pharmacokinet. 2006;45(4):325-50. [PubMed:16584282 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Bharucha AE, Ravi K, Zinsmeister AR: Comparison of selective M3 and nonselective muscarinic receptor antagonists on gastrointestinal transit and bowel habits in humans. Am J Physiol Gastrointest Liver Physiol. 2010 Jul;299(1):G215-9. doi: 10.1152/ajpgi.00072.2010. Epub 2010 Apr 15. [PubMed:20395537 ]
  2. Bozkurt TE, Sahin-Erdemli I: M(1) and M(3) muscarinic receptors are involved in the release of urinary bladder-derived relaxant factor. Pharmacol Res. 2009 May;59(5):300-5. doi: 10.1016/j.phrs.2009.01.013. Epub 2009 Feb 5. [PubMed:19416629 ]
  3. Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]
  2. Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I: Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. [PubMed:10374898 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]
  2. Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I: Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. [PubMed:10374898 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular weight:
53048.7
References
  1. Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]
  2. Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I: Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. [PubMed:10374898 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM5
Uniprot ID:
P08912
Molecular weight:
60073.2
References
  1. Moriya H, Takagi Y, Nakanishi T, Hayashi M, Tani T, Hirotsu I: Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8. [PubMed:10374898 ]
  2. Jha S, Parsons M: Treatment of overactive bladder in the aging population: focus on darifenacin. Clin Interv Aging. 2006;1(4):309-16. [PubMed:18046909 ]