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

General Information of Drug (ID: DR3390)
Drug Name
Imatinib
Synonyms
Cgp 57148; Glamox; Glamox (TN); Gleevec (TN); Glivec (TN); Imatinib (INN); Imatinib (STI571); Imatinib Methansulfonate; Imatinib [INN:BAN]; 112GI019; 152459-95-5; BKJ8M8G5HI; CCRIS 9076; CGP-57148; CHEMBL941; Imatinib free base; STI; UNII-BKJ8M8G5HI
Indication Chronic myelogenous leukaemia [ICD11: 2A20] Approved [1]
Mantle cell lymphoma [ICD11: ICD11: 2A85] Approved [2]
Intestinal cancer [ICD11: ICD11: 2C0Z] Phase 3 [3]
Lung cancer [ICD11: ICD11: 2C25] Phase 2 [4]
Mastocytosis [ICD11: ICD11: 2A21] Investigative [5]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 493.6 Topological Polar Surface Area 86.3
Heavy Atom Count 37 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
5291
ChEBI ID
CHEBI:45783
CAS Number
152459-95-5
TTD Drug ID
D0KG3Y
Formula
C29H31N7O
Canonical SMILES
CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5
InChI
InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
InChIKey
KTUFNOKKBVMGRW-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
N-Desmethylimatinib DM004309
9869737
Unclear - Unclear 1 [9]
Other imatinib metabolites DM019432 N. A. Unclear - Unclear 1 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012007 Imatinib N-desmethyl-imatinib Unclear - Unclear CYP3A4 ... [9]
MR012008 Imatinib Other imatinib metabolites Unclear - Unclear CYP1A2 ... [9]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[6]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[7]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[7]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[8]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[8]
⏷ Show the Full List of 6  DME(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5687).
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5687).
4 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5687).
5 Design and development of antisense drugs. Expert Opin. Drug Discov. 2008 3(10):1189-1207.
6 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
7 Plasma pharmacokinetics and CYP3A12-dependent metabolism of c-kit inhibitor imatinib in dogs
8 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
9 Role of cytochrome P450 activity in the fate of anticancer agents and in drug resistance: focus on tamoxifen, paclitaxel and imatinib metabolism

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