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

General Information of Drug (ID: DR1669)
Drug Name
Vandetanib
Synonyms
Vandetanib; Caprelsa; GNF-PF-2188; YO460OQ37K; ZD 6474; ZD-6474; ZD6474; Zactima; vandetanib (zd6474); 443913-73-3; C22H24BrFN4O2; CHEBI:49960; CHEMBL24828; N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-((1-methyl-4-piperidinyl)methoxy)-4-quinazolinamine; N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-amine; N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazolin-4-amine; NCGC00167513-01; UNII-YO460OQ37K
Indication Thyroid cancer [ICD11: 2D10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 475.4 Topological Polar Surface Area 59.5
Heavy Atom Count 30 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
3081361
PubChem SID
8030012 ; 8034317 ; 9471114 ; 12015522 ; 14716916 ; 14761077 ; 36412170 ; 46394288 ; 47208064 ; 49742597 ; 50068212 ; 50100123 ; 50112766 ; 50599279 ; 53789193 ; 57354678 ; 85246147 ; 91147360 ; 92721418 ; 93309619 ; 93581029 ; 93692935 ; 99436956 ; 99445235 ; 103194628 ; 103905338 ; 111682639 ; 123110212 ; 124756961 ; 124772087 ; 124893337 ; 124893338 ; 125163767 ; 125350704 ; 126619162 ; 126651857 ; 126661732 ; 126731545 ; 127330006 ; 127330007 ; 131333378 ; 131408693 ; 134339002 ; 134964431 ; 135228305 ; 135685324 ; 135685325 ; 135685344 ; 135697656 ; 135727395
ChEBI ID
ChEBI:49960
CAS Number
443913-73-3
TTD Drug ID
D0G6QF
Formula
C22H24BrFN4O2
Canonical SMILES
CN1CCC(CC1)COC2=C(C=C3C(=C2)N=CN=C3NC4=C(C=C(C=C4)Br)F)OC
InChI
1S/C22H24BrFN4O2/c1-28-7-5-14(6-8-28)12-30-21-11-19-16(10-20(21)29-2)22(26-13-25-19)27-18-4-3-15(23)9-17(18)24/h3-4,9-11,13-14H,5-8,12H2,1-2H3,(H,25,26,27)
InChIKey
UHTHHESEBZOYNR-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-desmethyl vandetanib DM003037
5329048
Oxidation - N-Demethylation 1 [3] , [4] , [5]
Vandetanib N-oxide DM003038
99738037
Oxidation - Oxidation 1 [3] , [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002502 Vandetanib N-desmethyl vandetanib Oxidation - N-Demethylation CYP3A4 [3], [4], [5]
MR002503 Vandetanib Vandetanib N-oxide Oxidation - Oxidation FMO1 ... [3], [5]
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]
Dimethylaniline oxidase 1 (FMO1) DME0059 Homo sapiens
FMO1_HUMAN
1.14.13.8
[3]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[3]
References
1 Vandetanib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA label of Vandetanib. The 2020 official website of the U.S. Food and Drug Administration.
3 Pharmacokinetics of vandetanib: three phase I studies in healthy subjects Clin Ther. 2012 Jan;34(1):221-37. doi: 10.1016/j.clinthera.2011.11.011.
4 Functional evaluation of vandetanib metabolism by CYP3A4 variants and potential drug interactions in vitro Chem Biol Interact. 2021 Dec 1;350:109700. doi: 10.1016/j.cbi.2021.109700.
5 Identification of Human Enzymes Oxidizing the Anti-Thyroid-Cancer Drug Vandetanib and Explanation of the High Efficiency of Cytochrome P450 3A4 in its Oxidation Int J Mol Sci. 2019 Jul 10;20(14):3392. doi: 10.3390/ijms20143392.

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