Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1616)
Drug Name
Tolterodine tartrate
Synonyms
Tolterodine (tartrate); Tolterodine tartrate (Detrol LA); Tolterodine tartrate [USAN]; UNII-5T619TQR3R; Tolterodina; Tolterodinum; UNII-WHE7A56U7K; Unidet; WHE7A56U7K; tolterodine; (+)-(R)-2-(alpha-(2-(Diisopropylamino)ethyl)benzyl)-p-cresol; (+)-Tolterodine; (R)-(+)-Tolterodine; 124937-51-5; 2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-methylphenol; CHEBI:9622; CHEMBL1382; DSSTox_CID_3687; DSSTox_GSID_23687; DSSTox_RID_77147; Kabi 2234; NCGC00159519-02; PNU 200583; Q-200223; S-(-)-Tolterodine; (+)-(R)-2-(I-(2-(Diisopropylamino)ethyl)benzyl)-p-cresol L-tartrate (1:1) (salt); (R)-2-(3-(Diisopropylamino)-1-phenylpropyl)-4-methylphenol (2R,3R)-2,3-dihydroxysuccinate; (R)-2-(3-Diisopropylamino-1-phenyl-propyl)-p-cresol L-tartrate; 124937-52-6; 5T619TQR3R; C26H37NO7; Detrol LA; PNU 200583E; PNU-200583E
Indication Overactive bladder [ICD11: GC50] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 475.6 Topological Polar Surface Area 139
Heavy Atom Count 34 Rotatable Bond Count 10
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
443878
CAS Number
124937-52-6
TTD Drug ID
D0BZ7W
Formula
C26H37NO7
Canonical SMILES
CC1=CC(=C(C=C1)O)C(CCN(C(C)C)C(C)C)C2=CC=CC=C2.C(C(C(=O)O)O)(C(=O)O)O
InChI
1S/C22H31NO.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h6-12,15-17,20,24H,13-14H2,1-5H3;1-2,5-6H,(H,7,8)(H,9,10)/t20-;1-,2-/m11/s1
InChIKey
TWHNMSJGYKMTRB-KXYUELECSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
5-Hydroxymethyl tolterodine DM000171
9819382
Oxidation - Methyl-hydroxylation 1 [4]
N-Dealkylated tolterodine DM006312
66731016
Oxidation - N-dealkylation 1 [4]
5-Carboxylic acid tolterodine DM006315
12049181
Unclear 2 [4]
N-Dealkylated 5-hydroxymethyl tolterodine DM006313
9966084
Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006780 Tolterodine tartrate N-Dealkylated tolterodine Oxidation - N-dealkylation CYP2C19 ... [4]
MR006782 Tolterodine tartrate 5-Hydroxymethyl tolterodine Oxidation - Methyl-hydroxylation Unclear [4]
MR006783 5-Hydroxymethyl tolterodine 5-Carboxylic acid tolterodine Unclear CYP2D6 [4]
MR006784 5-Hydroxymethyl tolterodine N-Dealkylated 5-hydroxymethyl tolterodine Unclear Unclear [4]
MR006781 N-Dealkylated tolterodine N-Dealkylated 5-hydroxymethyl tolterodine Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Tolterodine Tartrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Tolterodine, a new muscarinic receptor antagonist, is metabolized by cytochromes P450 2D6 and 3A in human liver microsomes. Drug Metab Dispos. 1998 Apr;26(4):289-93.
3 Effect of the CYP2D6*10 genotype on tolterodine pharmacokinetics. Drug Metab Dispos. 2010 Sep;38(9):1456-63.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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