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Trabectedin

Trabectedin structure

CAS No:
114899-77-3
Formula:
C39H43N3O11S
Chemical Name:
Trabectedin
Synonyms:
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)-;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-,[6R-(6α,6aβ,7β,13β,14β,16α,20R*)]-;(1′R,6R,6aR,7R,13S,14S,16R)-5-(Acetyloxy)-3′,4′,6,6a,7,13,14,16-octahydro-6′,8,14-trihydroxy-7′,9-dimethoxy-4,10,23-trimethylspiro[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;Ecteinascidine 743;Et 743;Ecteinascidin 743;NSC 648766;Trabectedin;Yondelis;Ecteinascidin
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

ChEBI: A tetrahydroisoquinoline alkaloid obtained from a Caribbean tunicate Ecteinascidia turbinata. Used for the treatment of soft tissue sarcoma and relapsed ovarian cancer.Trabectedin is a marine natural product derived from the tunicate Ecteinascidia turbinate. With its demonstrated in vitro and in vivo activity against a range of solid tumor cell lines, human xenografts and tumor explants, this antineoplastic agent has been developed and launched for the treatment of advanced STS after

Trabectedin is natural product derived from the Caribbean sea squirt which has antineoplastic activity and is used to treat soft tissue sarcoma. Trabectedin therapy is associated with a high rate of transient serum enzyme elevations during treatment and with occasional instances of clinically apparent liver injury with jaundice.|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 Basic Attributes

Molecular Weight：

761.845

Exact Mass：

761.84

DSSTox ID：

DTXSID2046880

Characteristics

PSA：

194.02000

XLogP3：

3.10

Appearance：

Solid

Density：

1.55±0.1 g/cm3 (20 ºC 760 Torr)

Refractive Index：

1.732

Water Solubility：

3.28e-01 g/L

Specific rotation：

D25 +114° (c = 0.1 in methanol)

Safety Information

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P312, P304+P340, P308+P313, P312, P314, P321, P322, P330, P363, P405, and P501|Aggregated GHS information provided by 8 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Hepatotoxicity：

Elevations in serum aminotransferase levels arise in almost all patients treated with trabectedin and elevations above 5 times the upper limit of normal occur 20% to 50% of patients. Pretreatment with dexamethasone appears to decrease the degree and frequency of enzyme elevations. The elevations arise within 2 to 5 days of the intravenous infusion, rise to maximal levels between 5 and 9 days and generally fall to baseline values within 3 to 4 weeks. Minor elevations in serum alkaline phosphatase and bilirubin are also common. However, clinically apparent liver injury with jaundice from trabectedin is rare. On the other hand, patients with underlying liver disease appear to be at increased risk for septicemia and multiorgan failure, and monitoring of liver tests before and during therapy is recommended. The liver injury typically mimics acute decompensation of an underlying cirrhosis with modest elevations in serum enzymes and worsening jaundice and hepatic synthetic dysfunction. Immunoallergic and autoimmune features are uncommon. Fatalities are generally due to sepsis and multiorgan failure.

Drug Information

LiverTox Summary：

Drug Classes：

Antineoplastic Agents, Alkylating Agents

MeSH：

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.)

MeSH Entry Terms：

ecteinascidin 743

Trabectedin Use and Manufacturing

A tetrahydroisoquinoline alkaloid with antitumor activity isolated from the Caribbean tunicate, Ecteinascidin turbinata. It is the first marine anticancer agent approved in the European Union for patients with soft tissue sarcoma (STS).

Computed Properties

Molecular Weight:761.8
XLogP3:3.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:4
Exact Mass:761.26183037
Monoisotopic Mass:761.26183037
Topological Polar Surface Area:194
Heavy Atom Count:54
Complexity:1450
Undefined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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