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Statements

Subject Item: n2:DB05109
rdf:type: n3:Drug
n3:description: Trabectedin, also referred as ET-743 during its development, is a marine derived antitumoral agent discovered in the Carribean tunicate _Ecteinascidia turbinata_ and now produced synthetically. Trabectedin has a unique mechanism of action. It binds to the minor groove of DNA interfering with cell division and genetic transcription processes and DNA repair machinery.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.
n3:dosage: n16:271B6429-363D-11E5-9242-09173F13E4C5
n3:generalReferences: # Tavecchio M, Natoli C, Ubezio P, Erba E, D'Incalci M: Dynamics of cell cycle phase perturbations by trabectedin (ET-743) in nucleotide excision repair (NER)-deficient and NER-proficient cells, unravelled by a novel mathematical simulation approach. Cell Prolif. 2007 Dec;40(6):885-904. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18021177 # Krasner CN, McMeekin DS, Chan S, Braly PS, Renshaw FG, Kaye S, Provencher DM, Campos S, Gore ME: A Phase II study of trabectedin single agent in patients with recurrent ovarian cancer previously treated with platinum-based regimens. Br J Cancer. 2007 Dec 17;97(12):1618-24. Epub 2007 Nov 13. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18000504 # Carter NJ, Keam SJ: Trabectedin : a review of its use in the management of soft tissue sarcoma and ovarian cancer. Drugs. 2007;67(15):2257-76. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17927287 # Trabectedin: Ecteinascidin 743, Ecteinascidin-743, ET 743, ET-743, NSC 684766. Drugs R D. 2006;7(5):317-28. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16922593 # Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19515014
n3:group: approved investigational
n3:halfLife: 33-50 hours
n3: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.
owl:sameAs: n6:DB05109 n18:DB05109
dcterms:title: Trabectedin
adms:identifier: n12:PA165958349 n13:Trabectedin n17:DB05109
n3:mechanismOfAction: 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.
n3:patent: n10:2373794 n10:2428160
n3:synonym: Ecteinascidin 743 SID144206315 SID144206787
n3:proteinBinding: 94 to 98%
n3:synthesisReference: Elias J. Corey, David Gin, "Process for producing ecteinascidin compounds." U.S. Patent US5721362, issued December, 1995.
n8:hasConcept: n9:M0453081
n3:IUPAC-Name: n4:271B642E-363D-11E5-9242-09173F13E4C5
n3:InChI: n4:271B6434-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula: n4:271B6433-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight: n4:271B6430-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight: n4:271B6431-363D-11E5-9242-09173F13E4C5
n3:SMILES: n4:271B6432-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility: n4:271B642C-363D-11E5-9242-09173F13E4C5
n3:logP: n4:271B642D-363D-11E5-9242-09173F13E4C5 n4:271B642A-363D-11E5-9242-09173F13E4C5
n3:logS: n4:271B642B-363D-11E5-9242-09173F13E4C5
n14:hasATCCode: n15:L01CX01
n3:H-Bond-Acceptor-Count: n4:271B643A-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count: n4:271B643B-363D-11E5-9242-09173F13E4C5
n3:InChIKey: n4:271B6435-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-: n4:271B6436-363D-11E5-9242-09173F13E4C5
n3:Polarizability: n4:271B6438-363D-11E5-9242-09173F13E4C5
n3:Refractivity: n4:271B6437-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count: n4:271B6439-363D-11E5-9242-09173F13E4C5
n3:absorption: Administered intravenously.
n3:affectedOrganism: Humans and other mammals
n3:casRegistryNumber: 114899-77-3
n3:category
n3:Bioavailability: n4:271B6440-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter: n4:271B6442-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule: n4:271B6443-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings: n4:271B643F-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge: n4:271B643E-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five: n4:271B6441-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name: n4:271B642F-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-: n4:271B643C-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-: n4:271B643D-363D-11E5-9242-09173F13E4C5