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

General Information of Drug (ID: DR1696)
Drug Name
Vinorelbine tartrate
Synonyms
Vinorelbine Bitartrate; Vinorelbine ditartrate; Vinorelbine tartrate; Vinorelbine L-tartrate; Vinorelbine ditartaric acid; Vinorelbine, ditartrate; Vinorelbina; Vinorelbina [Spanish]; Vinorelbine (INN); Vinorelbine [INN:BAN]; Vinorelbine(Navelbine); Vinorelbinum; Vinorelbinum [Latin]; methyl (2b,3b,4b,5a,12b,19a)-4-(acetyloxy)-15-[(6R,8S)-4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate; Vinorelbine; 71486-22-1; C45H54N4O8; CHEBI:480999; Eunades; Exelbine; KW 2307 base; KW-2307; Navelbine; Navelbine (TN); Nor-5'-anhydrovinblastine; Q6C979R91Y; UNII-Q6C979R91Y; 125317-39-7; 3',4'-DIDEHYDRO-4'-DEOXY-C'-NORVINCALEUKOBLASTINE R-(R*,R*)-2-3-DIHYDROXYBUTANEDIOATE (1:2) SALT; 3',4'-Didehydro-4'-deoxy-C'-norvincaleukoblastine [R-(R*,R*)-2-3-dihydroxybutanedioate (1:2)salt]; 317V397; 5'-Noranhydrovinoblastine tartrate; AB15572; MFCD03613607; NVB; Navelbine tartrate; Q-100110; VINORELBINE DITARTRATE SALT
Indication Lung cancer [ICD11: 2C25] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 1079.1 Topological Polar Surface Area 364
Heavy Atom Count 77 Rotatable Bond Count 16
Hydrogen Bond Donor Count 10 Hydrogen Bond Acceptor Count 23
Cross-matching ID
PubChem CID
45055483
CAS Number
125317-39-7
TTD Drug ID
D01HTL
Formula
C53H66N4O20
Canonical SMILES
CCC1=CC2CC(C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC.C(C(C(=O)O)O)(C(=O)O)O.C(C(C(=O)O)O)(C(=O)O)O
InChI
1S/C45H54N4O8.2C4H6O6/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7;2*5-1(3(7)8)2(6)4(9)10/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t28-,37+,38-,39-,42-,43-,44+,45+;2*1-,2-/m111/s1
InChIKey
CILBMBUYJCWATM-LNLXBTRNSA-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
20'-hydroxyvinorelbine DM005274
6426844
Oxidation - Hydrolyzationn 1 [4]
4-O-deacetyl Vinorelbine DM005273
21783126
Unclear 1 [4] , [5]
Vinorelbine N-oxide DM005275
101656270
Oxidation - Oxidationn 1 [4] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013240 Vinorelbine tartrate 4-O-deacetyl Vinorelbine Unclear Unclear [4], [5]
MR013241 Vinorelbine tartrate 20'-hydroxyvinorelbine Oxidation - Hydrolyzationn Unclear [4]
MR013242 Vinorelbine tartrate Vinorelbine N-oxide Oxidation - Oxidationn Unclear [4], [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
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
[3]
References
1 Vinorelbine Tartrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
3 Characterization of human cytochrome P450 isoenzymes involved in the metabolism of vinorelbine. Fundam Clin Pharmacol. 2005 Oct;19(5):545-53.
4 New sensitive liquid chromatography method coupled with tandem mass spectrometric detection for the clinical analysis of vinorelbine and its metabolites in blood, plasma, urine and faeces
5 Sensitive determination of vinorelbine and its metabolites in human serum using liquid chromatography-electrospray mass spectrometry

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