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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:53 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
Data?1582753266
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, tolterodineHMDB
DetrolHMDB
Detrol laHMDB
UrotrolHMDB
LA, detrolHMDB
UnidetHMDB
DetrusitolHMDB
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
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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0053 g/LNot Available
LogP5.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM182.130932474
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.1731661259
DarkChem[M-H]-179.03731661259
DeepCCS[M+H]+185.57430932474
DeepCCS[M-H]-183.21630932474
DeepCCS[M-2H]-217.26430932474
DeepCCS[M+Na]+192.49130932474
AllCCS[M+H]+182.032859911
AllCCS[M+H-H2O]+178.932859911
AllCCS[M+NH4]+184.932859911
AllCCS[M+Na]+185.732859911
AllCCS[M-H]-189.832859911
AllCCS[M+Na-2H]-190.232859911
AllCCS[M+HCOO]-190.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TolterodineCC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(O)C=CC(C)=C1)C(C)C3214.9Standard polar33892256
TolterodineCC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(O)C=CC(C)=C1)C(C)C2254.2Standard non polar33892256
TolterodineCC(C)N(CC[C@H](C1=CC=CC=C1)C1=C(O)C=CC(C)=C1)C(C)C2371.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tolterodine,1TMS,isomer #1CC1=CC=C(O[Si](C)(C)C)C([C@H](CCN(C(C)C)C(C)C)C2=CC=CC=C2)=C12384.7Semi standard non polar33892256
Tolterodine,1TBDMS,isomer #1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([C@H](CCN(C(C)C)C(C)C)C2=CC=CC=C2)=C12593.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tolterodine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03kd-7951000000-3385c328a55a06acf3092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolterodine GC-MS (1 TMS) - 70eV, Positivesplash10-007o-8559000000-cf481e1eca35cdd592042017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolterodine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolterodine LC-ESI-qTof , Positive-QTOFsplash10-000t-2911000000-6586d7c95e03f623dbf42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolterodine , positive-QTOFsplash10-000t-2911000000-6586d7c95e03f623dbf42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolterodine 35V, Positive-QTOFsplash10-007k-1911000000-c0fd6127be48bf2f7a232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolterodine 35V, Negative-QTOFsplash10-00di-0009000000-083c5ad346fffc212d7b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 10V, Positive-QTOFsplash10-004i-0029000000-8ebe9b5f6a86293c37392016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 20V, Positive-QTOFsplash10-004i-2495000000-1ed1c923b6a81337be092016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 40V, Positive-QTOFsplash10-05r3-6960000000-12167a7ccb72ad279c232016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 10V, Negative-QTOFsplash10-00di-0109000000-e41fd8abdd5bbe7804b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 20V, Negative-QTOFsplash10-00di-1549000000-b035309354f1b53e1c3a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 40V, Negative-QTOFsplash10-0pb9-5910000000-a1268da3a9be37b286002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 10V, Positive-QTOFsplash10-004i-0698000000-a31f373ee765ece4d0872021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 20V, Positive-QTOFsplash10-004i-2981000000-0ca47d3e62b83c05482e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 40V, Positive-QTOFsplash10-014i-2920000000-4e26799c6b02e71d70272021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 10V, Negative-QTOFsplash10-00di-0009000000-10db0ede3d3f2006c8112021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 20V, Negative-QTOFsplash10-05fr-1956000000-ff4e0782925fae4e823c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolterodine 40V, Negative-QTOFsplash10-060r-3930000000-92f0a25e8b4a83c2d2102021-10-11Wishart 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 DB01036 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01036 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01036
Phenol Explorer Compound IDNot Available
FooDB 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
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