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

General Information of Drug (ID: DR0387)
Drug Name
Crizotinib
Synonyms
Crizotinib; Crizotinib (PF-02341066); Crizotinib (PF-2341066); PF 02341066; PF 2341066; PF-02341066; PF-2341066; PF2341066; Xalkori; crizotinibum; (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine; (R)-crizotinib; 3-[(1R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1H-pyrazol-4-yl]-2-pyridinamine; 53AH36668S; 877399-52-5; CHEBI:64310; CHEMBL601719; UNII-53AH36668S
Indication Lung cancer [ICD11: 2C25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 450.3 Topological Polar Surface Area 78
Heavy Atom Count 30 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
11626560
PubChem SID
16729581 ; 23733583 ; 74374126 ; 75543391 ; 93581001 ; 99309272 ; 99437209 ; 99445171 ; 103728028 ; 104161043 ; 119526687 ; 121278669 ; 124490471 ; 124756975 ; 125163780 ; 125299329 ; 126659900 ; 131407280 ; 135264650 ; 135668295 ; 135727397 ; 136345871 ; 136367829 ; 136920405 ; 137232008 ; 137275901 ; 141226597 ; 143499147 ; 152040652 ; 152134626 ; 152237527 ; 152258843 ; 152344161 ; 160644611 ; 160647693 ; 160815247 ; 160969694 ; 162010188 ; 162010189 ; 162011538 ; 162196520 ; 162927269 ; 163565316 ; 163590241 ; 164041842 ; 164193931 ; 165245564 ; 170497919 ; 174531154 ; 175265614
ChEBI ID
CHEBI:64310
CAS Number
877399-52-5
TTD Drug ID
D03ZBT
Formula
C21H22Cl2FN5O
Canonical SMILES
CC(C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N
InChI
1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1
InChIKey
KTEIFNKAUNYNJU-GFCCVEGCSA-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
Crizotinib metabolite M10 DM003728 N. A. Unclear 1 [3]
Crizotinib metabolite M4 DM003733 N. A. Unclear 1 [3]
PF-06260182 DM003737
131668046
Oxidation - Oxidationn 1 [4]
Crizotinib metabolite M1 DM003736 N. A. Unclear 2 [3]
Crizotinib metabolite M2 DM003729
156613778
Unclear 2 [3]
Crizotinib metabolite M3 DM003734 N. A. Unclear 2 [3]
Crizotinib metabolite M5 DM003735 N. A. Multi-steps Reaction - Hydrolyzationn; Glucuronidation 2 [3]
Crizotinib metabolite M6 DM003731 N. A. Unclear 3 [3]
Crizotinib metabolite M6 DM003731 N. A. Oxidation - Hydrolyzationn 3 [3]
Crizotinib metabolite M8 DM003732 N. A. Unclear 3 [3]
Crizotinib metabolite M9 DM003730 N. A. Unclear 3 [3]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004117 Crizotinib Crizotinib metabolite M10 Unclear Unclear [3]
MR004122 Crizotinib Crizotinib metabolite M4 Unclear Unclear [3]
MR004127 Crizotinib PF-06260182 Oxidation - Oxidationn Unclear [4]
MR004118 Crizotinib metabolite M10 Crizotinib metabolite M2 Unclear Unclear [3]
MR004123 Crizotinib metabolite M4 Crizotinib metabolite M2 Unclear Unclear [3]
MR004124 Crizotinib metabolite M4 Crizotinib metabolite M3 Unclear Unclear [3]
MR004125 Crizotinib metabolite M4 Crizotinib metabolite M5 Multi-steps Reaction - Hydrolyzationn; Glucuronidation Unclear [3]
MR004126 Crizotinib metabolite M4 Crizotinib metabolite M1 Unclear Unclear [3]
MR004119 Crizotinib metabolite M2 Crizotinib metabolite M9 Unclear Unclear [3]
MR004120 Crizotinib metabolite M2 Crizotinib metabolite M6 Oxidation - Hydrolyzationn Unclear [3]
MR004121 Crizotinib metabolite M2 Crizotinib metabolite M8 Unclear Unclear [3]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
References
1 Crizotinib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Crizotinib for the treatment of non-small-cell lung cancer. Am J Health Syst Pharm. 2013 Jun 1;70(11):943-7.
3 Metabolism, excretion and pharmacokinetics of [14C]crizotinib following oral administration to healthy subjects
4 DrugBank(Pharmacology-Metabolism):Crizotinib

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