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1. Ecteinascidin 743
2. Et 743
3. Et-743
4. Et743
5. Nsc 684766
6. Yondelis
1. Yondelis
2. Ecteinascidin
3. Ecteinascidin 743
4. Et-743
5. 114899-77-3
6. Ect 743
7. Et743
8. Id0yzq2tcp
9. Et 743
10. Ecteinascidins Trabectedin
11. Chebi:84050
12. Nsc-648766
13. [(1r,2r,3r,11s,12s,14r,26r)-5,6',12-trihydroxy-6,7'-dimethoxy-7,21,30-trimethyl-27-oxospiro[17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaene-26,1'-3,4-dihydro-2h-isoquinoline]-22-yl] Acetate
14. Dsstox_cid_26880
15. Dsstox_rid_81984
16. Dsstox_gsid_46880
17. Trabectedin [inn]
18. Ecteinascidine 743
19. Ecteinascidin-743
20. Cas-114899-77-3
21. Unii-id0yzq2tcp
22. Nsc 648766
23. Nsc 684766
24. Trabectedin [usan:inn:ban]
25. Ccris 8133
26. Ncgc00181159-01
27. Ncgc00181159-02
28. Trabectedin [jan]
29. Trabectedin [usan]
30. Trabectedin [mart.]
31. Trabectedin [who-dd]
32. Trabectedin [ema Epar]
33. Chembl450449
34. Gtpl2774
35. Dtxsid2046880
36. Schembl12119916
37. Trabectedin [orange Book]
38. Ex-a4317
39. Tox21_112762
40. Tox21_113236
41. Nsc813783
42. Zinc150338708
43. Cs-1608
44. Db05109
45. Ecteinascidins Trabectedin [mi]
46. Nsc-684766
47. Nsc-813783
48. (1'r,6r,6ar,7r,13s,14s,16r)-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-3',4',6,7,12,13,14,16-octahydrospiro(6,16-(epithiopropanooxymethano)-7,13-imino-6ah-1,3-dioxolo(7,8)isoquino(3,2-b)(3)benzazocine-20,1'(2'h)-isoquinolin)-5-yl Acetate
49. Ac-27767
50. Ecteinascidin 743;et-743;ecteinascidin
51. Hy-50936
52. Spiro(6,16-(epithiopropanoxymethano)-7,13-imino-12h-1,3-dioxolo(7,8)isoquino(3,2,-b)(3)benzazocine-20,1'(2'h)-isoquinolin)-19-one, 3',4',6,6a,7,13,14,16-octahydro-5-(acetyloxy)-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-, (6r-(6-alpha,6a-beta,7-beta,13-beta,14-beta,16-alpha,20r*))-
53. Spiro(6,16-(epithiopropanoxymethano)-7,13-imino-12h-1,3-dioxolo(7,8)isoquino(3,2,-b)(3)benzazocine-20,1'(2'h)-isoquinolin)-19-one, 5-(acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-, (1'r,6r,6ar,7r,13s,14s,16r)-
54. Q2637746
55. (1r,2r,3r,11s,12s,14r,26r)-5,6',12-trihydroxy-6,7'-dimethoxy-7,21,30-trimethyl-27-oxo-3',4'-dihydro-2'h-17,19,28-trioxa-24-thia-13,30-diazaspiro[heptacyclo[12.9.6.1^{3,11}.0^{2,13}.0^{4,9}.0^{15,23}.0^{16,20}]triacontane-26,1'-isoquinoline]-4(9),5,7,15(23),16(20),21-hexaen-22-yl Acetate
56. (6r,6ar,7r,13s,14s,16r,20r)-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-3',4',6,7,12,13,14,16-octahydro-2'h,6ah-spiro[7,13-epimino-6,16-(epithiopropanooxymethano)[1,3]dioxolo[7,8]isoquinolino[3,2-b][3]benzazocine-20,1'-isoquinolin]-5-yl Acetate
| Molecular Weight | 761.8 g/mol |
|---|---|
| Molecular Formula | C39H43N3O11S |
| XLogP3 | 3.4 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 15 |
| Rotatable Bond Count | 4 |
| Exact Mass | 761.26183037 g/mol |
| Monoisotopic Mass | 761.26183037 g/mol |
| Topological Polar Surface Area | 194 Ų |
| Heavy Atom Count | 54 |
| Formal Charge | 0 |
| Complexity | 1450 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 7 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Indicated for treatment of advanced soft tissue sarcoma in patients refractory to or unsuitable to receive anthracycline or ifosfamide chemotherapy in Europe, Russia and South Korea. Approved for orphan drug status by the U.S. FDA for treatment of soft tissue sarcomas and ovarian cancer. Investigated for use/treatment in cancer/tumors (unspecified), gastric cancer, ovarian cancer, pediatric indications, sarcoma, and solid tumors.
FDA Label
Yondelis is indicated for the treatment of patients with advanced soft-tissue sarcoma, after failure of anthracyclines and ifosfamide, or who are unsuited to receive these agents. Efficacy data are based mainly on liposarcoma and leiomyosarcoma patients.
Yondelis in combination with pegylated liposomal doxorubicin (PLD) is indicated for the treatment of patients with relapsed platinum-sensitive ovarian cancer .
Yondelis is indicated for the treatment of patients with advanced soft tissue sarcoma, having failed antracyclines and ifosfamide, or having failed ifosfamide and unsuitable to receive antracyclines/ifosfamide.
Two of the rings in the drug's structure allows it to covalently bind to the minor groove of DNA. The third ring protrudes from the DNA which lets it interact with nearby nuclear proteins. This has the additive effect of blocking cell division at the G2 phase.
Antineoplastic Agents, Alkylating
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)
L01CX01
L01CX01
L01CX01
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
L - Antineoplastic and immunomodulating agents
L01 - Antineoplastic agents
L01C - Plant alkaloids and other natural products
L01CX - Other plant alkaloids and natural products
L01CX01 - Trabectedin
Absorption
Administered intravenously.
33-50 hours
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.
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