General
Preferred name
trabectedin
Synonyms
Ecteinascidin ()
Yondelis ()
Et743 ()
ECTEINASCIDIN 743 ()
Trabectedina ()
NSC-648766 ()
Ecteinascidins trabectedin ()
Trabectedine ()
ET-743 ()
P&D ID
PD009337
CAS
114899-77-3
Tags
available
drug
natural product
Approved by
FDA
PMDA
EMA
First approval
2007
Drug indication
Solid tumour/cancer
Ovarian cancer
Drug Status
withdrawn
approved
investigational
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA
Trabectedin interacts with the minor groove of DNA and alkylates guanine at the N2 position, which bends towards the major groove. In this manner, it is thought that the drug affects various transcription factors involved in cell proliferation, particularly via the transcription-coupled nucleotide excision repair system. Trabectedin blocks the cell cycle at the G2 phase, while cells at the G1 phase are most sensitive to the drug. It also inhibits overexpression of the multidrug resistance-1 gene (MDR-1) coding for the P-glycoprotein that is a major factor responsible for cells developing resistance to cancer drugs. The agent is also thought to interfere with the nucleotide excision repair pathways of cancer cells, suggesting that it could be effective in the treatment of many cancer types including melanoma and sarcoma, as well as lung, breast, ovarian, endometrial and prostate cancers; clinical evaluations are underway in these indications.;
DESCRIPTION
The ecteinascidins (Ets) are natural products derived from the marine tunicate Ecteinascidia turbinata. Being a natural substance, there is some ambiguity in the literature as to the exact chemical structure of trabectedin, therefore representations of the compound on the external resource links may vary slightly from that shown here. Trabectedin is now produced synthetically. Mechanistically trabectedin is a DNA minor groove binder and it forms covalent bonds with the exocyclic amino group of certain guanines in the minor groove and interstrand crosslinks via van der Waals interactions and hydrogen bonds .
(GtoPdb)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
3
Organisms
0
Compound Sets
15
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Guide to Pharmacology
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
ReFrame library
Withdrawn 2.0
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
34
Molecular Weight
761.26
Hydrogen Bond Acceptors
15
Hydrogen Bond Donors
4
Rotatable Bonds
3
Ring Count
10
Aromatic Ring Count
3
cLogP
3.41
TPSA
168.72
Fraction CSP3
0.49
Chiral centers
7.0
Largest ring
10.0
QED
0.23
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
MOA
antitumor agent
ATC
L01CX01
Biosynthetic Origin
Peptide (NRPS)
Therapeutic Indication
Anticancer
Source data
