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Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:27 UTC
HMDB IDHMDB0015170
Secondary Accession Numbers
  • HMDB15170
Metabolite Identification
Common NameTolterodine
DescriptionTolterodine is only found in individuals that have used or taken this drug. It is an antimuscarinic drug that is used to treat urinary incontinence. Tolterodine acts on M2 and M3 subtypes of muscarinic receptors.Both tolterodine and its active metabolite, 5-hydroxymethyltolterodine, act as competitive antagonists at muscarinic receptors. This antagonism results in inhibition of bladder contraction, decrease in detrusor pressure, and an incomplete emptying of the bladder.
Structure
Thumb
Synonyms
ValueSource
(+)-(R)-2-(alpha-(2-(diisopropylamino)Ethyl)benzyl)-P-cresolChEBI
(+)-TolterodineChEBI
TolterodinaChEBI
TolterodinumChEBI
(+)-(R)-2-(a-(2-(diisopropylamino)Ethyl)benzyl)-P-cresolGenerator
(+)-(R)-2-(α-(2-(diisopropylamino)ethyl)benzyl)-P-cresolGenerator
Tolterodine extended release capsulesHMDB
Tolterodine L-tartrateHMDB
Tolterodine tartrateHMDB
Tolterondine tartrateHMDB
Tartrate, tolterodineMeSH
DetrolMeSH
Detrol laMeSH
UrotrolMeSH
LA, detrolMeSH
UnidetMeSH
DetrusitolMeSH
Chemical FormulaC22H31NO
Average Molecular Weight325.4876
Monoisotopic Molecular Weight325.240564619
IUPAC Name2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
Traditional Name(+)-tolterodine
CAS Registry Number124937-51-5
SMILES
CC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(O)C=CC(C)=C1)C(C)C
InChI Identifier
InChI=1S/C22H31NO/c1-16(2)23(17(3)4)14-13-20(19-9-7-6-8-10-19)21-15-18(5)11-12-22(21)24/h6-12,15-17,20,24H,13-14H2,1-5H3/t20-/m1/s1
InChI KeyOOGJQPCLVADCPB-HXUWFJFHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These 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
  • P-cresol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Toluene
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0053 g/LNot Available
LogP5.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP5.39ALOGPS
logP5.12ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)11.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity103.96 m³·mol⁻¹ChemAxon
Polarizability39.27 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03kd-7951000000-3385c328a55a06acf309View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007o-8559000000-cf481e1eca35cdd59204View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000t-2911000000-6586d7c95e03f623dbf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000t-2911000000-6586d7c95e03f623dbf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0029000000-8ebe9b5f6a86293c3739View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2495000000-1ed1c923b6a81337be09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05r3-6960000000-12167a7ccb72ad279c23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0109000000-e41fd8abdd5bbe7804b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1549000000-b035309354f1b53e1c3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-5910000000-a1268da3a9be37b28600View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01036 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01036 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01036
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID391967
KEGG Compound IDC07750
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolterodine
METLIN IDNot Available
PubChem Compound443879
PDB IDNot Available
ChEBI ID9622
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available