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

General Information of Drug (ID: DR1523)
Drug Name
Tacrine hydrochloride
Synonyms
Tacrine HCl; Tacrine hydrochloride; Tenakrin; UNII-4966RNG0BU; tacrine.HCl; Tacrina [INN-Spanish]; Tacrine; Tacrine [INN:BAN]; Tacrinum; Tacrinum [INN-Latin]; Tetrahydroaminacrine; Tetrahydroaminoacridine; Tetrahydroaminocrin; Tetrahydroaminocrine; UNII-4VX7YNB537; 1,2,3,4-TETRAHYDRO-9-ACRIDINAMINE; 1,2,3,4-Tetrahydro-9-aminoacridine; 1,2,3,4-tetrahydroacridin-9-amine; 321-64-2; 5-Amino-6,7,8,9-tetrahydroacridine (European); 9-Acridinamine, 1,2,3,4-tetrahydro-; 9-amino-1,2,3,4-tetrahydroacridine; Acridine, 1,2,3,4-tetrahydro-9-amino-; CHEMBL95; CS 12602; Cognex; EINECS 206-291-2; 1,2,3,4-Tetrahydro-9-acridinamine hydrochloride; 1,2,3,4-Tetrahydro-9-acridinamine monohydrochloride; 1,2,3,4-tetrahydroacridin-9-amine hydrochloride; 1684-40-8; 4966RNG0BU; 9-AMINO-1,2,3,4-TETRAHYDROACRIDINE HYDROCHLORIDE; 9-Acridinamine, 1,2,3,4-tetrahydro-, monohydrochloride; AK-60389; CCRIS 7250; CI 970; CI-970; CPD000059105; EINECS 216-867-5; Hydroaminacrine; MLS000028845; NSC 72108; SMR000059105
Indication Alzheimer disease [ICD11: 8A20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 234.72 Topological Polar Surface Area 38.9
Heavy Atom Count 16 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2723754
CAS Number
1684-40-8
TTD Drug ID
D0E6YQ
Formula
C13H15ClN2
Canonical SMILES
C1CCC2=NC3=CC=CC=C3C(=C2C1)N.Cl
InChI
1S/C13H14N2.ClH/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13;/h1,3,5,7H,2,4,6,8H2,(H2,14,15);1H
InChIKey
ZUFVXZVXEJHHBN-UHFFFAOYSA-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
1-hydroxytacrine DM000415
3655
Oxidation - Hydroxylation 1 [2]
2-hydroxytacrine DM000417
179849
Oxidation - Hydroxylation 1 [2]
3-hydroxytacrine DM019934
10104685
Oxidation - Hydroxylation 1 [2]
4- Hydroxytacrine DM000416
179850
Oxidation - Hydroxylation 1 [2]
5,6-diOH-tacrine DM019937 N. A. Oxidation - Hydroxylation 1 [2]
7-hydroxytacrine DM000418
10104685
Oxidation - Hydroxylation 1 [2]
8-hydroxytacrine DM019936 N. A. Oxidation - Hydroxylation 1 [2]
Glutathione conjugation of tacrine DM000420 N. A. Conjugation - Glutathione Conjugation 1 [3]
1,3-diOH-tacrine DM019933 N. A. Oxidation - Hydroxylation 2 [2]
7,8-diOH-tacrine DM019935 N. A. Oxidation - Hydroxylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002896 Tacrine hydrochloride 1-hydroxytacrine Oxidation - Hydroxylation Unclear [2]
MR002897 Tacrine hydrochloride 4- Hydroxytacrine Oxidation - Hydroxylation Unclear [2]
MR002898 Tacrine hydrochloride 2-hydroxytacrine Oxidation - Hydroxylation Unclear [2]
MR002899 Tacrine hydrochloride 7-hydroxytacrine Oxidation - Hydroxylation CYP1A2 ... [2]
MR002900 Tacrine hydrochloride Glutathione conjugation of tacrine Conjugation - Glutathione Conjugation GSTT1 ... [3]
MR002902 Tacrine hydrochloride 3-hydroxytacrine Oxidation - Hydroxylation Unclear [2]
MR002905 Tacrine hydrochloride 8-hydroxytacrine Oxidation - Hydroxylation Unclear [2]
MR002907 Tacrine hydrochloride 5,6-diOH-tacrine Oxidation - Hydroxylation Unclear [2]
MR002901 1-hydroxytacrine 1,3-diOH-tacrine Oxidation - Hydroxylation Unclear [2]
MR002903 3-hydroxytacrine 1,3-diOH-tacrine Oxidation - Hydroxylation Unclear [2]
MR002904 7-hydroxytacrine 7,8-diOH-tacrine Oxidation - Hydroxylation Unclear [2]
MR002906 8-hydroxytacrine 7,8-diOH-tacrine Oxidation - Hydroxylation Unclear [2]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[3]
Glutathione S-transferase mu-1 (GSTM1) DME0308 Homo sapiens
GSTM1_HUMAN
2.5.1.18
[4]
Glutathione S-transferase theta-1 (GSTT1) DME0093 Homo sapiens
GSTT1_HUMAN
2.5.1.18
[4]
⏷ Show the Full List of 6  DME(s)
References
1 Tacrine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.
3 Combined glutathione-S-transferase M1 and T1 genetic polymorphism and tacrine hepatotoxicity. Clin Pharmacol Ther. 2000 Apr;67(4):432-7.
4 Combined glutathione-S-transferase M1 and T1 genetic polymorphism and tacrine hepatotoxicity Clin Pharmacol Ther. 2000 Apr;67(4):432-7. doi: 10.1067/mcp.2000.104944.

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