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

General Information of Drug (ID: DR0669)
Drug Name
Etoposide
Synonyms
Eposin; Etopophos (phosphate salt); Etoposide (VP16); Etoposido; Etoposido [INN-Spanish]; Etoposidum; Etoposidum [INN-Latin]; Lastet; NK 171; Toposar; VP 16 (pharmaceutical); VP 16-213; VP 16213; VP-16-213; VePesid; Vepesid J; Zuyeyidal; etoposide; trans-Etoposide; (-)-Etoposide; 33419-42-0; 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside); 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside; CCRIS 2392; EINECS 251-509-1; HSDB 6517; NSC 141540; NSC-141540; UNII-6PLQ3CP4P3; VP 16; VP-16
Indication Lung cancer [ICD11: 2C25] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 588.6 Topological Polar Surface Area 161
Heavy Atom Count 42 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 13
Cross-matching ID
PubChem CID
36462
PubChem SID
4733 ; 597749 ; 7847193 ; 7979208 ; 8145856 ; 8174504 ; 11110521 ; 12013288 ; 14886949 ; 14935915 ; 24278178 ; 24769897 ; 34677904 ; 46386954 ; 46500626 ; 46505434 ; 47362874 ; 48182835 ; 48332078 ; 49681767 ; 49699016 ; 49855364 ; 53787668 ; 56463308 ; 57311878 ; 71825014 ; 75974183 ; 85148351 ; 85788790 ; 89850276 ; 92308660 ; 92308790 ; 99437037 ; 104019076 ; 104234176 ; 104324084 ; 117664408 ; 117682510 ; 119525100 ; 121363248 ; 124349593 ; 124659141 ; 124757097 ; 124800231 ; 124893613 ; 125163901 ; 127298729 ; 127298730 ; 127298731 ; 127298732
ChEBI ID
ChEBI:4911
CAS Number
33419-42-0
TTD Drug ID
D0B7EB
Formula
C29H32O13
Canonical SMILES
CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
InChI
1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
InChIKey
VJJPUSNTGOMMGY-MRVIYFEKSA-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
3'-demethyletoposide DM000949
131770008
Oxidation - 3'-Demethylation 1 [7]
Etoposide catechol DM000947
127462
Unclear 1 [5]
Etoposide glucuronide DM000950
4488109
Conjugation - Glucuronidation 1 [8]
Etoposide ortho-quinone DM000948
76320713
Unclear 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000982 Etoposide Etoposide catechol Unclear CYP3A4 ... [5]
MR000983 Etoposide 3'-demethyletoposide Oxidation - 3'-Demethylation CYP3A4 [7]
MR000984 Etoposide Etoposide glucuronide Conjugation - Glucuronidation UGT1A1 [8]
MR000981 Etoposide catechol Etoposide ortho-quinone Unclear MPO [8]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
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
[4]
Glutathione S-transferase pi (GSTP1) DME0088 Homo sapiens
GSTP1_HUMAN
2.5.1.18
[5]
Glutathione S-transferase theta-1 (GSTT1) DME0093 Homo sapiens
GSTT1_HUMAN
2.5.1.18
[5]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[6]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Homo sapiens
PGH2_HUMAN
1.14.99.1
[6]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[7]
⏷ Show the Full List of 9  DME(s)
References
1 Etoposide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
3 A study on the metabolism of etoposide and possible interactions with antitumor or supporting agents by human liver microsomes. J Pharmacol Exp Ther. 1998 Sep;286(3):1294-300.
4 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
5 Reactions of glutathione with the catechol, the ortho-quinone and the semi-quinone free radical of etoposide. Consequences for DNA inactivation. Biochem Pharmacol. 1992 Apr 15;43(8):1761-8.
6 Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Biochem Biophys Res Commun. 1986 Feb 26;135(1):215-20.
7 UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab Dispos. 2007 Mar;35(3):371-80.
8 DrugBank(Pharmacology-Metabolism)Etoposide

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