Tolterodine (CED0005624)

Record Information

Version

1.0

Creation Date

2016-05-22 03:47:26 UTC

Update Date

2026-08-21 23:00:21 UTC

Accession Number

CHEM016914

Identification

Common Name

Tolterodine

Class

Small Molecule

Description

Tolterodine is an organic compound with the chemical formula C22H31NO and an average molecular weight of 325.49 g/mol. Tolterodine belongs to the diphenylmethanes, a subclass of benzene and substituted derivatives within the organic compounds. It is classified under the superclass of benzenoids. This compound is found in or released from one recorded source: healthcare, pharmaceuticals & veterinary products, specifically urologicals. The recorded route of exposure for this substance is oral. Tolterodine acts upon five recorded protein targets. It functions as an antagonist of the Muscarinic acetylcholine receptor M1 (CHRM1), Muscarinic acetylcholine receptor M2 (CHRM2), Muscarinic acetylcholine receptor M3 (CHRM3), and Muscarinic acetylcholine receptor M4 (CHRM4), in addition to one other protein.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(R)-2-(alpha-(2-(Diisopropylamino)ethyl)benzyl)-p-cresol	ChEBI
(+)-Tolterodine	ChEBI
Tolterodina	ChEBI
Tolterodinum	ChEBI
(+)-(R)-2-(a-(2-(Diisopropylamino)ethyl)benzyl)-p-cresol	Generator
(+)-(R)-2-(Α-(2-(diisopropylamino)ethyl)benzyl)-p-cresol	Generator
Tolterodine extended release capsules	HMDB
Tolterodine L-tartrate	HMDB
Tolterodine tartrate	HMDB
Tolterondine tartrate	HMDB
Tartrate, tolterodine	HMDB
Detrol	HMDB
Detrol la	HMDB
Urotrol	HMDB
LA, detrol	HMDB
Unidet	HMDB
Detrusitol	HMDB

Chemical Formula

C₂₂H₃₁NO

Average Molecular Mass

325.488 g/mol

Monoisotopic Mass

325.241 g/mol

CAS Registry Number

124937-51-5

IUPAC Name

2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol

Traditional Name

(+)-tolterodine

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 Key

OOGJQPCLVADCPB-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amine (CHEBI:9622 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0053 g/L	ALOGPS
logP	5.39	ALOGPS
logP	5.12	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	11.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.96 m³·mol⁻¹	ChemAxon
Polarizability	39.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-03kd-7951000000-3385c328a55a06acf309	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-007o-8559000000-cf481e1eca35cdd59204	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000t-2911000000-6586d7c95e03f623dbf4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000t-2911000000-6586d7c95e03f623dbf4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-007k-1911000000-c0fd6127be48bf2f7a23	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0009000000-083c5ad346fffc212d7b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0029000000-8ebe9b5f6a86293c3739	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-2495000000-1ed1c923b6a81337be09	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05r3-6960000000-12167a7ccb72ad279c23	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0109000000-e41fd8abdd5bbe7804b1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-1549000000-b035309354f1b53e1c3a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pb9-5910000000-a1268da3a9be37b28600	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0698000000-a31f373ee765ece4d087	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-2981000000-0ca47d3e62b83c05482e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-2920000000-4e26799c6b02e71d7027	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-10db0ede3d3f2006c811	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05fr-1956000000-ff4e0782925fae4e823c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-060r-3930000000-92f0a25e8b4a83c2d210	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
690.0	Log mg/kg	[390:1200]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
326	Urologicals	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

2 pathways

Tolterodine Action Pathway

Tolterodine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	5.68299
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	1.94623
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	2.80257
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	4.04816
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	12.6894
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	164.962
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	87.0354
Click to view 3D structure	Muscarinic acetylcholine receptor M3	Q8VH26	Cavia porcellus	Predicted (SEA)	3.65891
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P08482	Rattus norvegicus	Predicted (SEA)	11.1324
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P10980	Rattus norvegicus	Predicted (SEA)	11.5995
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P08483	Rattus norvegicus	Predicted (SEA)	3.73676
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	30.439
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08485	Rattus norvegicus	Predicted (SEA)	2.64687
Click to view 3D structure	Sodium channel protein type 5 subunit alpha	Q14524	Humans	Predicted (SEA)	66.5611
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	153.441
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08911	Rattus norvegicus	Predicted (SEA)	1.55698
Click to view 3D structure	Voltage-dependent L-type calcium channel subunit alpha-1C	O35505	Cavia porcellus	Predicted (SEA)	1.40129
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	135.302
Click to view 3D structure	CX3C chemokine receptor 1	P49238	Humans	Predicted (SEA)	1.86838
Click to view 3D structure	Apelin receptor	P35414	Humans	Predicted (SEA)	12.1445
Click to view 3D structure	Free fatty acid receptor 4	Q5NUL3	Humans	Predicted (SEA)	28.9599
Click to view 3D structure	Glucose-dependent insulinotropic receptor	Q8TDV5	Humans	Predicted (SEA)	4.43741
Click to view 3D structure	C5a anaphylatoxin chemotactic receptor 1	P21730	Humans	Predicted (SEA)	95.5988
Click to view 3D structure	C3a anaphylatoxin chemotactic receptor	Q16581	Humans	Predicted (SEA)	5.68299
Click to view 3D structure	Glucagon-like peptide 1 receptor	P43220	Humans	Predicted (SEA)	145.189