Trabectedin | CAS#114899-77-3 | Antitumor drug

MedKoo Cat#: 341244 | Name: Trabectedin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Trabectedin (also known as ecteinascidin 743 or ET-743, trade name Yondelis) is an antitumor chemotherapy drug sold by Pharma Mar S.A. and Johnson and Johnson under the brand name Yondelis. It is approved for use in Europe, Russia, and South Korea for the treatment of advanced soft-tissue sarcoma. It is also undergoing clinical trials for the treatment of breast, prostate, and paediatric sarcomas. The European Commission and the U.S. Food and Drug Administration (FDA) have granted orphan drug status to trabectedin for soft-tissue sarcomas and ovarian cancer.

Chemical Structure

Trabectedin

CAS#114899-77-3

Theoretical Analysis

MedKoo Cat#: 341244

Name: Trabectedin

CAS#: 114899-77-3

Chemical Formula: C39H43N3O11S

Exact Mass: 761.2618

Molecular Weight: 761.84

Elemental Analysis: C, 61.49; H, 5.69; N, 5.52; O, 23.10; S, 4.21

Price and Availability

Size	Price	Availability
1mg	USD 450.00	Ready to ship
5mg	USD 550.00	Ready to ship
10mg	USD 950.00	Ready to ship
25mg	USD 1,650.00	Ready to ship
100mg	USD 4,650.00	2 Weeks
1g	USD 12,950.00	2 Weeks

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Related CAS #

No Data

Synonym

Trabectedin; ET-743; ET 743; ET743; Ecteinascidin 743; NSC 648766; NSC648766; NSC- 648766;

IUPAC/Chemical 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

InChi Key

PKVRCIRHQMSYJX-RJZIEWFPSA-N

InChi Code

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?/m1/s1

SMILES Code

CC1=C(OC)C(O)=C2C3[C@@H]4[C@@H]5C6=C(C7=C(OCO7)C(C)=C6OC(C)=O)[C@@H](COC(C8(C9=CC(OC)=C(O)C=C9CCN8)CS5)=O)N4C(O)C(CC2=C1)N3C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Certificate of Analysis

View CoA: current batch, Lot#T25D01P23

QC Data

View QC data: current batch, Lot#T25D01P23

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 761.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Larsen AK, Galmarini CM, D'Incalci M. Unique features of trabectedin mechanism of action. Cancer Chemother Pharmacol. 2016 Apr;77(4):663-71. doi: 10.1007/s00280-015-2918-1. Epub 2015 Dec 14. PMID: 26666647. 2: Cucè M, Gallo Cantafio ME, Siciliano MA, Riillo C, Caracciolo D, Scionti F, Staropoli N, Zuccalà V, Maltese L, Di Vito A, Grillone K, Barbieri V, Arbitrio M, Di Martino MT, Rossi M, Amodio N, Tagliaferri P, Tassone P, Botta C. Trabectedin triggers direct and NK-mediated cytotoxicity in multiple myeloma. J Hematol Oncol. 2019 Mar 21;12(1):32. doi: 10.1186/s13045-019-0714-9. PMID: 30898137; PMCID: PMC6429746. 3: D'Incalci M, Zambelli A. Trabectedin for the treatment of breast cancer. Expert Opin Investig Drugs. 2016;25(1):105-15. doi: 10.1517/13543784.2016.1124086. Epub 2015 Dec 22. PMID: 26592307. 4: Zijoo R, von Mehren M. Efficacy of trabectedin for the treatment of liposarcoma. Expert Opin Pharmacother. 2016 Oct;17(14):1953-62. doi: 10.1080/14656566.2016.1229304. Epub 2016 Sep 15. PMID: 27615729. 5: Tumini E, Herrera-Moyano E, San Martín-Alonso M, Barroso S, Galmarini CM, Aguilera A. The Antitumor Drugs Trabectedin and Lurbinectedin Induce Transcription-Dependent Replication Stress and Genome Instability. Mol Cancer Res. 2019 Mar;17(3):773-782. doi: 10.1158/1541-7786.MCR-18-0575. Epub 2018 Dec 14. PMID: 30552231; PMCID: PMC6398590. 6: Demetri GD, von Mehren M, Jones RL, Hensley ML, Schuetze SM, Staddon A, Milhem M, Elias A, Ganjoo K, Tawbi H, Van Tine BA, Spira A, Dean A, Khokhar NZ, Park YC, Knoblauch RE, Parekh TV, Maki RG, Patel SR. Efficacy and Safety of Trabectedin or Dacarbazine for Metastatic Liposarcoma or Leiomyosarcoma After Failure of Conventional Chemotherapy: Results of a Phase III Randomized Multicenter Clinical Trial. J Clin Oncol. 2016 Mar 10;34(8):786-93. doi: 10.1200/JCO.2015.62.4734. Epub 2015 Sep 14. PMID: 26371143; PMCID: PMC5070559. 7: Teplinsky E, Herzog TJ. The efficacy of trabectedin in treating ovarian cancer. Expert Opin Pharmacother. 2017 Feb;18(3):313-323. doi: 10.1080/14656566.2017.1285282. PMID: 28140689. 8: De Sanctis R, Marrari A, Santoro A. Trabectedin for the treatment of soft tissue sarcomas. Expert Opin Pharmacother. 2016 Aug;17(11):1569-77. doi: 10.1080/14656566.2016.1204295. Epub 2016 Jul 4. PMID: 27328277. 9: Stacchiotti S, Mir O, Le Cesne A, Vincenzi B, Fedenko A, Maki RG, Somaiah N, Patel S, Brahmi M, Blay JY, Boye K, Sundby Hall K, Gelderblom H, Hindi N, Martin-Broto J, Kosela H, Rutkowski P, Italiano A, Duffaud F, Kobayashi E, Casali PG, Provenzano S, Kawai A. Activity of Pazopanib and Trabectedin in Advanced Alveolar Soft Part Sarcoma. Oncologist. 2018 Jan;23(1):62-70. doi: 10.1634/theoncologist.2017-0161. Epub 2017 Jul 28. PMID: 28754721; PMCID: PMC5759809. 10: Monk BJ, Lorusso D, Italiano A, Kaye SB, Aracil M, Tanović A, D'Incalci M. Trabectedin as a chemotherapy option for patients with BRCA deficiency. Cancer Treat Rev. 2016 Nov;50:175-182. doi: 10.1016/j.ctrv.2016.09.009. Epub 2016 Sep 15. PMID: 27710871. 11: Ray-Coquard I. Trabectedin mechanism of action and platinum resistance: molecular rationale. Future Oncol. 2017 Oct;13(23s):17-21. doi: 10.2217/fon-2017-0318. Epub 2017 Oct 11. PMID: 29020822. 12: Harlow ML, Chasse MH, Boguslawski EA, Sorensen KM, Gedminas JM, Kitchen- Goosen SM, Rothbart SB, Taslim C, Lessnick SL, Peck AS, Madaj ZB, Bowman MJ, Grohar PJ. Trabectedin Inhibits EWS-FLI1 and Evicts SWI/SNF from Chromatin in a Schedule-dependent Manner. Clin Cancer Res. 2019 Jun 1;25(11):3417-3429. doi: 10.1158/1078-0432.CCR-18-3511. Epub 2019 Feb 5. PMID: 30723142; PMCID: PMC6594545. 13: Gordon EM, Sankhala KK, Chawla N, Chawla SP. Trabectedin for Soft Tissue Sarcoma: Current Status and Future Perspectives. Adv Ther. 2016 Jul;33(7):1055-71. doi: 10.1007/s12325-016-0344-3. Epub 2016 May 27. PMID: 27234989; PMCID: PMC4939148. 14: Ventriglia J, Paciolla I, Cecere SC, Pisano C, Di Napoli M, Arenare L, Setola SV, Losito NS, Califano D, Orditura M, Pignata S. Trabectedin in Ovarian Cancer: is it now a Standard of Care? Clin Oncol (R Coll Radiol). 2018 Aug;30(8):498-503. doi: 10.1016/j.clon.2018.01.008. Epub 2018 Feb 9. PMID: 29429842. 15: Villanucci A, Tavella K, Vannini L, Rossi V, Nobili S, Amunni G, Mazzei T, Mini E. Trabectedin in combination with pegylated liposomal doxorubicin in patients with ovarian tumors. Mol Clin Oncol. 2018 Dec;9(6):635-639. doi: 10.3892/mco.2018.1729. Epub 2018 Oct 1. PMID: 30546893; PMCID: PMC6256111. 16: Banerjee P, Zhang R, Ivan C, Galletti G, Clise-Dwyer K, Barbaglio F, Scarfò L, Aracil M, Klein C, Wierda W, Plunkett W, Caligaris-Cappio F, Gandhi V, Keating MJ, Bertilaccio MTS. Trabectedin Reveals a Strategy of Immunomodulation in Chronic Lymphocytic Leukemia. Cancer Immunol Res. 2019 Dec;7(12):2036-2051. doi: 10.1158/2326-6066.CIR-19-0152. Epub 2019 Sep 17. PMID: 31530560; PMCID: PMC6891195. 17: Carminati L, Pinessi D, Borsotti P, Minoli L, Giavazzi R, D'Incalci M, Belotti D, Taraboletti G. Antimetastatic and antiangiogenic activity of trabectedin in cutaneous melanoma. Carcinogenesis. 2019 Apr 29;40(2):303-312. doi: 10.1093/carcin/bgy177. PMID: 30544170. 18: Kawai A, Yonemori K, Takahashi S, Araki N, Ueda T. Systemic Therapy for Soft Tissue Sarcoma: Proposals for the Optimal Use of Pazopanib, Trabectedin, and Eribulin. Adv Ther. 2017 Jul;34(7):1556-1571. doi: 10.1007/s12325-017-0561-4. Epub 2017 May 25. PMID: 28547734; PMCID: PMC5504216. 19: Petek BJ, Loggers ET, Pollack SM, Jones RL. Trabectedin in soft tissue sarcomas. Mar Drugs. 2015 Feb 12;13(2):974-83. doi: 10.3390/md13020974. PMID: 25686274; PMCID: PMC4344612. 20: Romano M, Della Porta MG, Gallì A, Panini N, Licandro SA, Bello E, Craparotta I, Rosti V, Bonetti E, Tancredi R, Rossi M, Mannarino L, Marchini S, Porcu L, Galmarini CM, Zambelli A, Zecca M, Locatelli F, Cazzola M, Biondi A, Rambaldi A, Allavena P, Erba E, D'Incalci M. Antitumour activity of trabectedin in myelodysplastic/myeloproliferative neoplasms. Br J Cancer. 2017 Jan;116(3):335-343. doi: 10.1038/bjc.2016.424. Epub 2017 Jan 10. PMID: 28072764; PMCID: PMC5294481.