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9EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: Yondelis, Ecteinascidin, Ecteinascidin 743, Et-743, 114899-77-3, Ect 743

Molecular Formula

C₃₉H₄₃N₃O₁₁S

Molecular Weight

761.8 g/mol

InChI Key

PKVRCIRHQMSYJX-AIFWHQITSA-N

FDA UNII

ID0YZQ2TCP

A complex structure that includes isoquinolines joined by a cyclic ester; it is a DNA-binding agent and guanine N2 alkylator derived from the marine tunicate, Ecteinascidia turbinata. Trabectedin is used for the treatment of advanced soft-tissue SARCOMA, after failure of ANTHRACYCLINES or IFOSFAMIDE drug therapy.

Trabectedin is an Alkylating Drug. The mechanism of action of trabectedin is as an Alkylating Activity.

1 2D Structure

Trabectedin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(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

2.1.2 InChI

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

2.1.3 InChI Key

PKVRCIRHQMSYJX-AIFWHQITSA-N

2.1.4 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

2.1.5 Isomeric SMILES

CC1=CC2=C([C@@H]3[C@@H]4[C@H]5C6=C(C(=C7C(=C6[C@@H](N4[C@H]([C@H](C2)N3C)O)COC(=O)[C@@]8(CS5)C9=CC(=C(C=C9CCN8)O)OC)OCO7)C)OC(=O)C)C(=C1OC)O

2.2 Other Identifiers

2.2.1 UNII

ID0YZQ2TCP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ecteinascidin 743

2. Et 743

3. Et-743

4. Et743

5. Nsc 684766

6. Yondelis

2.3.2 Depositor-Supplied Synonyms

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

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₃₉H₄₃N₃O₁₁S
Molecular Weight	761.8 g/mol
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 Å²
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

4 Drug and Medication Information

4.1 Drug Indication

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.

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

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.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

TRABECTEDIN

5.3.2 FDA UNII

ID0YZQ2TCP

5.3.3 Pharmacological Classes

Alkylating Drug [EPC]; Alkylating Activity [MoA]

5.4 ATC Code

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

5.5 Absorption, Distribution and Excretion

Absorption

Administered intravenously.

5.6 Biological Half-Life

33-50 hours

5.7 Mechanism of Action

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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