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

General Information of Drug (ID: DR1625)
Drug Name
Trabectedin
Synonyms
Trabectedin; Yondelis; ET-743; Ect 743; Ecteinascidin; Ecteinascidine 743; Et 743; ecteinascidin 743; 114899-77-3; CHEBI:84050; DSSTox_CID_26880; DSSTox_GSID_46880; DSSTox_RID_81984; ET743; ID0YZQ2TCP; NSC 648766; NSC 684766; UNII-ID0YZQ2TCP
Indication Leiomyosarcoma [ICD11: 2B58] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 761.8 Topological Polar Surface Area 194
Heavy Atom Count 54 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 15
Cross-matching ID
PubChem CID
108150
PubChem SID
10234617 ; 12014180 ; 14938004 ; 16067487 ; 44437036 ; 50047052 ; 50757578 ; 53788207 ; 57338466 ; 99443229 ; 104380621 ; 123092462 ; 126666934 ; 127334906 ; 127334907 ; 135256695 ; 135652680 ; 142813748 ; 144206315 ; 144206787 ; 160967837 ; 164765699 ; 184812413 ; 198978374 ; 223655497 ; 223736343 ; 237230406 ; 243425761 ; 252552191
ChEBI ID
CHEBI:84050
CAS Number
114899-77-3
TTD Drug ID
D03RTK
Formula
C39H43N3O11S
Canonical SMILES
CC1=CC2=C(C3C4C5C6=C(C(=C7C(=C6C(N4C(C(C2)N3C)O)COC(=O)C8(CS5)C9=CC(=C(C=C9CCN8)O)OC)OCO7)C)OC(=O)C)C(=C1OC)O
InChI
1S/C39H43N3O11S/c1-16-9-20-10-22-37(46)42-23-13-50-38(47)39(21-12-25(48-5)24(44)11-19(21)7-8-40-39)14-54-36(30(42)29(41(22)4)26(20)31(45)32(16)49-6)28-27(23)35-34(51-15-52-35)17(2)33(28)53-18(3)43/h9,11-12,22-23,29-30,36-37,40,44-46H,7-8,10,13-15H2,1-6H3/t22-,23-,29+,30+,36+,37-,39+/m0/s1
InChIKey
PKVRCIRHQMSYJX-AIFWHQITSA-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
Trabectedin metabolite M11a DM002346 N. A. Oxidation - Oxidation 1 [4]
Trabectedin metabolite M16c DM002352
156596924
Oxidation - O-Demethylation 1 [4]
Trabectedin metabolite M16e DM002349
155928963
Oxidation - Oxidation; Carboxylic Acid Formation 1 [4]
Trabectedin metabolite M4b DM002343 N. A. Oxidation - Demethylation; Oxidation 1 [4]
Trabectedin metabolite M8a DM002348
156596858
Unclear 1 [4]
Trabectedin metabolite M8b DM002351
9875331
Oxidation - N-Demethylation 1 [4]
Trabectedin metabolite M9 DM002353 N. A. Unclear 1 [4]
Trabectedin metabolite M16b DM002347 N. A. Oxidation - Oxidation 2 [4]
Trabectedin metabolite M16d DM002350 N. A. Oxidation - Oxidation 2 [4]
Trabectedin metabolite M16e DM002349
155928963
Oxidation - Oxidation 2 [4]
Trabectedin metabolite M4a DM002344 N. A. Oxidation - Oxidation 2 [4]
Trabectedin metabolite M8c DM002345 N. A. Unclear 3 [4]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002428 Trabectedin Trabectedin metabolite M4b Oxidation - Demethylation; Oxidation Unclear [4]
MR002429 Trabectedin Trabectedin metabolite M11a Oxidation - Oxidation Unclear [4]
MR002430 Trabectedin Trabectedin metabolite M8a Unclear Unclear [4]
MR002431 Trabectedin Trabectedin metabolite M16e Oxidation - Oxidation; Carboxylic Acid Formation Unclear [4]
MR002432 Trabectedin Trabectedin metabolite M8b Oxidation - N-Demethylation Unclear [4]
MR002433 Trabectedin Trabectedin metabolite M16c Oxidation - O-Demethylation Unclear [4]
MR002434 Trabectedin Trabectedin metabolite M9 Unclear Unclear [4]
MR002426 Trabectedin metabolite M11a Trabectedin metabolite M16b Oxidation - Oxidation Unclear [4]
MR002423 Trabectedin metabolite M4b Trabectedin metabolite M4a Oxidation - Oxidation Unclear [4]
MR002424 Trabectedin metabolite M4b Trabectedin metabolite M16d Oxidation - Oxidation Unclear [4]
MR002427 Trabectedin metabolite M8a Trabectedin metabolite M16e Oxidation - Oxidation Unclear [4]
MR002425 Trabectedin metabolite M4a Trabectedin metabolite M8c Unclear Unclear [4]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[3]
⏷ Show the Full List of 7  DME(s)
References
1 Trabectedin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro characterization of the human biotransformation and CYP reaction phenotype of ET-743 (Yondelis, Trabectidin), a novel marine anti-cancer drug. Invest New Drugs. 2006 Jan;24(1):3-14.
3 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
4 In vitro studies on the metabolism of trabectedin (YONDELIS) in monkey and man, including human CYP reaction phenotyping Biochem Pharmacol. 2009 May 15;77(10):1642-54. doi: 10.1016/j.bcp.2009.02.020.

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