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Compound Detail

CHEMBL450449

TRABECTEDIN
💊 Approved Drug
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💊 Approved Drug
COc1cc2c(cc1O)CCN[C@]21CS[C@@H]2c3c(OC(C)=O)c(C)c4c(c3[C@H](COC1=O)N1[C@@H]2[C@H]2c3c(cc(C)c(OC)c3O)C[C@@H]([C@@H]1O)N2C)OCO4
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL450449
Name TRABECTEDIN
Phase Approved
Structure Type MOL
InChI Key PKVRCIRHQMSYJX-AIFWHQITSA-N
Therapeutic ✓ Yes

Known Names

Ecteinascidin 743 Ecteinascidins trabectedin ET-743 Et743 NSC-648766 Trabectedin Trabectedina Trabectedine Yondelis
1
Targets
1
Activities
1
Assay Types
3
PK Parameters
20
Publications
9
Known Names
20
Indications
1
Mechanisms

Molecular Properties

761.9
MW (Da)
3.41
ALogP
15
HBA
4
HBD
168.7
PSA (Ų)
0.23
QED
2
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2007
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -ectedin
USAN Year 2004

Extended Properties

Molecular Formula C39H43N3O11S
MW 761.85
Aromatic Rings 3
Heavy Atoms 54
NP-Likeness 1.56

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA ✓ ✓

Indications

Leiomyosarcoma Liposarcoma Liposarcoma Neoplasms Neoplasms Ovarian Neoplasms Ovarian Neoplasms Ovarian Neoplasms Sarcoma Sarcoma Breast Neoplasms Carcinoma, Ovarian Epithelial Chondrosarcoma, Mesenchymal Endocrine Gland Neoplasms Fallopian Tube Neoplasms Hereditary Breast and Ovarian Cancer Syndrome Liposarcoma, Myxoid Meningioma Mesothelioma Mesothelioma

ATC Classification

L01CX01
trabectedin
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 1 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ADMET
CHEMBL612558
 IC50 8.22 8.22 6.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 12.0 mL.min-1.kg-1 Homo sapiens
MRT 35.0 hr Homo sapiens
T1/2 44.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ADMET IC50 = 6.0 nM 8.22 Effect on cell cycle distribution in Chinese hamster homologous recombination re... 17656556

Literature References

PubMed DOI Target Context # Activities
17656556 10.1073/pnas.0609877104 Unchecked 10
17656556 10.1073/pnas.0609877104 HeLa 6
17656556 10.1073/pnas.0609877104 CHO-AA8 6
17656556 10.1073/pnas.0609877104 V79 6
18426954 10.1124/dmd.108.020479 ADMET 4
17656556 10.1073/pnas.0609877104 NON-PROTEIN TARGET 4
20709558 10.1016/j.bmc.2010.07.049 A549 3
20709558 10.1016/j.bmc.2010.07.049 HT-29 3
20709558 10.1016/j.bmc.2010.07.049 MDA-MB-231 3
20014752 10.1021/tx900326k Hepatotoxicity 3
18799316 10.1016/j.bmc.2008.07.083 MDA-MB-231 3
18799316 10.1016/j.bmc.2008.07.083 A549 3
18799316 10.1016/j.bmc.2008.07.083 HT-29 3
17656556 10.1073/pnas.0609877104 ADMET 2
17656556 10.1073/pnas.0609877104 CCRF-CEM 2
28675836 10.1016/j.ejmech.2017.06.047 ATP-dependent translocase ABCB1 1
17656556 10.1073/pnas.0609877104 Lymphocyte 1
16252925 10.1021/np050247f HT-29 1
16252925 10.1021/np050247f MDA-MB-231 1
17070059 10.1016/j.bmc.2006.10.009 HT-29 1

Data from ChEMBL 36 via Core Engine