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

General Information of Drug (ID: DR0603)
Drug Name
Erlotinib hydrochloride
Synonyms
Erlotinib (Hydrochloride); Erlotinib HCl (OSI-744); Erlotinib hydrochloride; Erlotinib; J4T82NDH7E; N-(3-Ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine; N-(3-Ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine; NCGC00164574-01; UNII-J4T82NDH7E; [6,7-BIS(2-METHOXY-ETHOXY)QUINAZOLINE-4-YL]-(3-ETHYNYLPHENYL)AMINE; 183321-74-6; 4-Quinazolinamine, N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-; 4-[(3-Ethynylphenyl)amino]-6,7-bis(2-methoxyethoxy)quinazoline; AK142763; CHEBI:114785; CHEMBL553; CP358774; DSSTox_CID_26454; DSSTox_GSID_46454; DSSTox_RID_81628; MFCD07781272; N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine hydrochloride; NSC-718781; OSI 774; Tarceva; UNII-DA87705X9K; erlotinib HCl; (CP358774; 183319-69-9; 4-Quinazolinamine, N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-, hydrochloride (1:1); 6,7-bis(2-methoxyethoxy)-4-(3-ethynylanilino)quinazoline hcl; 6,7-bis(2-methoxyethoxy)-4-(3-ethynylanilino)quinazoline hydrochloride; CP 358774; CP-358774; DA87705X9K
Indication Lung cancer [ICD11: 2C25] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 429.9 Topological Polar Surface Area 74.7
Heavy Atom Count 30 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
176871
ChEBI ID
CHEBI:53509
CAS Number
183321-74-6
TTD Drug ID
D07POC
Formula
C22H24ClN3O4
Canonical SMILES
COCCOC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC=CC(=C3)C#C)OCCOC
InChI
1S/C22H23N3O4/c1-4-16-6-5-7-17(12-16)25-22-18-13-20(28-10-8-26-2)21(29-11-9-27-3)14-19(18)23-15-24-22/h1,5-7,12-15H,8-11H2,2-3H3,(H,23,24,25)
InChIKey
GTTBEUCJPZQMDZ-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
Erlotinib M11 DM019959
71315775
Oxidation - Oxidation 1 [2]
Erlotinib M13 DM019952
16045730
Oxidation - O-demethylation 1 [2]
Erlotinib M14 DM019954
10317566
Oxidation - O-demethylation 1 [2] , [3]
Erlotinib M16 DM019960
74963268
Unclear 1 [2]
Erlotinib M17 DM019956
156596548
Unclear 1 [2]
Erlotinib M18 DM019957 N. A. Oxidation - O-demethylation 1 [2]
Erlotinib M6 DM019973
76969213
Oxidation - O-demethylation 1 [2]
Erlotinib M10 DM019955 N. A. Conjugation - O-glucuronidation 2 [2]
Erlotinib M11 DM019959
71315775
Oxidation - Oxidation 2 [2]
Erlotinib M12 DM019958
16045656
Conjugation - O-glucuronidation 2 [2]
Erlotinib M17 DM019956
156596548
Unclear 2 [2]
Erlotinib M17 DM019956
156596548
Conjugation - O-glucuronidation 2 [2]
Erlotinib M18 DM019957 N. A. Conjugation - O-glucuronidation 2 [2]
Erlotinib M2 DM019953 N. A. Unclear 2 [2]
Erlotinib M3 DM019962 N. A. Unclear 2 [2]
Erlotinib M7 DM019961 N. A. Conjugation - O-glucuronidation 2 [2]
Erlotinib M9 DM019963 N. A. Unclear 2 [2]
Erlotinib M14 DM019954
10317566
Oxidation - O-demethylation 3 [2] , [3]
Erlotinib M10 DM019955 N. A. Conjugation - O-glucuronidation 4 [2]
Erlotinib M12 DM019958
16045656
Conjugation - O-glucuronidation 4 [2]
Erlotinib M17 DM019956
156596548
Unclear 4 [2]
Erlotinib M18 DM019957 N. A. Conjugation - O-glucuronidation 4 [2]
⏷ Show the Full List of 22  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003005 Erlotinib hydrochloride Erlotinib M13 Oxidation - O-demethylation [2]
MR003013 Erlotinib hydrochloride Erlotinib M16 Unclear [2]
MR003018 Erlotinib hydrochloride Erlotinib M14 Oxidation - O-demethylation CYP3A4 ... [2], [3]
MR003019 Erlotinib hydrochloride Erlotinib M17 Unclear [2]
MR003020 Erlotinib hydrochloride Erlotinib M18 Oxidation - O-demethylation [2]
MR003021 Erlotinib hydrochloride Erlotinib M11 Oxidation - Oxidation [2]
MR003022 Erlotinib hydrochloride Erlotinib M6 Oxidation - O-demethylation [2]
MR003006 Erlotinib M13 Erlotinib M2 Unclear [2]
MR003012 Erlotinib M13 Erlotinib M11 Oxidation - Oxidation [2]
MR003014 Erlotinib M16 Erlotinib M7 Conjugation - O-glucuronidation [2]
MR003015 Erlotinib M16 Erlotinib M3 Unclear UGT [2]
MR003016 Erlotinib M16 Erlotinib M9 Unclear [2]
MR003017 Erlotinib M16 Erlotinib M17 Conjugation - O-glucuronidation [2]
MR003007 Erlotinib M2 Erlotinib M14 Oxidation - O-demethylation CYP3A4 ... [2], [3]
MR003008 Erlotinib M14 Erlotinib M10 Conjugation - O-glucuronidation [2]
MR003009 Erlotinib M14 Erlotinib M17 Unclear [2]
MR003010 Erlotinib M14 Erlotinib M18 Conjugation - O-glucuronidation [2]
MR003011 Erlotinib M14 Erlotinib M12 Conjugation - O-glucuronidation [2]
⏷ Show the Full List of 18 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
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
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
UDP-glucuronyltransferase (UGT) DMEN064 . Not Available Not Available [2]
⏷ Show the Full List of 6  DME(s)
References
1 Erlotinib 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 Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706.
4 In vitro assessment of time-dependent inhibitory effects on CYP2C8 and CYP3A activity by fourteen protein kinase inhibitors. Drug Metab Dispos. 2014 Jul;42(7):1202-9.

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