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

General Information of Drug (ID: DR0582)
Drug Name
Entrectinib
Synonyms
Entrectinib; Entrectinib (RXDX-101); Entrectinib [USAN:INN]; Entrectinib, 95%; L5ORF0AN1I; NMS-E628; RXDX-101; Rozlytrek; 1108743-60-7; Benzamide, N-(5-((3,5-difluorophenyl)methyl)-1H-indazol-3-yl)-4-(4-methyl-1-piperazinyl)-2-((tetrahydro-2H-pyran-4-yl)amino)-; Benzamide, N-[5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-yl]-4-(4-methyl-1-piperazinyl)-2-[(tetrahydro-2H-pyran-4-yl)amino]-; N-[5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-yl]-4-(4-methylpiperazin-1-yl)-2-(oxan-4-ylamino)benzamide; UNII-L5ORF0AN1I; YMX
Indication Lung cancer [ICD11: 2C25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 560.6 Topological Polar Surface Area 85.5
Heavy Atom Count 41 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
25141092
PubChem SID
56468453 ; 85003850 ; 103905026 ; 141279489 ; 223686891 ; 224447706 ; 229522507 ; 242521480 ; 246344423 ; 246919954 ; 249748717 ; 252164339 ; 252166502
CAS Number
1108743-60-7
TTD Drug ID
D0O0LS
Formula
C31H34F2N6O2
Canonical SMILES
CN1CCN(CC1)C2=CC(=C(C=C2)C(=O)NC3=NNC4=C3C=C(C=C4)CC5=CC(=CC(=C5)F)F)NC6CCOCC6
InChI
1S/C31H34F2N6O2/c1-38-8-10-39(11-9-38)25-3-4-26(29(19-25)34-24-6-12-41-13-7-24)31(40)35-30-27-17-20(2-5-28(27)36-37-30)14-21-15-22(32)18-23(33)16-21/h2-5,15-19,24,34H,6-14H2,1H3,(H2,35,36,37,40)
InChIKey
HAYYBYPASCDWEQ-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
ENB477 DM006403 N. A. Reduction - Reduction 1 [3]
ENB547 DM006402
25176014
Oxidation - N-dealkylation 1 [3]
ENB577b DM006398 N. A. Oxidation - Hydrolyzationn 1 [3]
ENB577c DM006400 N. A. Oxidation - N-oxidation 1 [3]
ENB579b DM006401 N. A. Reduction - Reduction 2 [3]
ENB753 DM006399 N. A. Conjugation - O-glucuronidation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006875 Entrectinib ENB577b Oxidation - Hydrolyzationn Unclear [3]
MR006877 Entrectinib ENB577c Oxidation - N-oxidation Unclear [3]
MR006879 Entrectinib ENB547 Oxidation - N-dealkylation CYP3A4 [3]
MR006880 Entrectinib ENB477 Reduction - Reduction Unclear [3]
MR006876 ENB577b ENB753 Conjugation - O-glucuronidation Unclear [3]
MR006878 ENB577c ENB579b Reduction - Reduction Unclear [3]
⏷ Show the Full List of 6 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]
References
1 Entrectinib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Entrectinib: first global approval. Drugs. 2019 Sep;79(13):1477-1483.
3 LC-MS/MS reveals the formation of iminium and quinone methide reactive intermediates in entrectinib metabolism: In vivo and in vitro metabolic investigation

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.