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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)- (114899-77-3)

Identification
Name: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)-
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-,[6R-(6a,6ab,7b,13b,14b,16a,20R*)]-;Ecteinascidin 743;Ecteinascidine 743;Et 743;NSC 648766;Trabectedin;Yondelis;
CAS:114899-77-3
Molecular Formula: C39H43N3O11S
Molecular Weight: 761.91
InChI: InChI=1/C40H45N3O11S/c1-17-11-21-12-23-38(47)43-24-15-51-39(48)40(22-14-26(49-5)25(45)13-20(22)7-9-41-40)8-10-55-37(31(43)30(42(23)4)27(21)32(46)33(17)50-6)29-28(24)36-35(52-16-53-36)18(2)34(29)54-19(3)44/h11,13-14,23-24,30-31,37-38,41,45-47H,7-10,12,15-16H2,1-6H3/t23-,24-,30+,31+,37+,38-,40+/m0/s1
Molecular Structure: (C39H43N3O11S) Spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20...
Properties
Flash Point: °C
Boiling Point: °Cat760mmHg
Density:1.53g/cm3
Refractive index:1.723
Specification:

  Ecteinascidin 743, with cas registry number of 114899-77-3, is a kind of heterocyclic compounds based on its structure. According to its biological activity, it will belong to Antineoplastic agents. Its systematic name is (6R,6aR,7R,13S,14S,16R,20R)-6',8,14-trihydroxy-7',9-dimethoxy-4,10,24-trimethyl-19-oxo-3',4',6,7,12,13,14,16-octahydro-2'H,6aH-spiro[7,13-epimino-6,16-(epithiobutanooxymethano)[1,3]dioxolo[7,8]isoquin o[3,2-b][3]benzazocine-20,1'-isoquinolin]-5-yl acetate . Its brand name is Yondelis . Besides these names, it is also called Trabectedin [INN] ; Trabectedin ; (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 ; CCRIS 8133 ; ET-743 ; Ect 743 ; Ecteinascidine 743 ; Et 743 ; NSC 648766 ; UNII-ID0YZQ2TCP .

 Ecteinascidin 743 is from Alkaloid from the ascidian Ecteinascidia turbinata. It was first determined by KL Rinehart at the University of Illinois in 1984. Ecteinascidin 743 had the anticancer activity. If it was used as a drug, it had to been done the further research in clinical trial. But at that time, the extracted yields were extremely low. Scientists begn to find the synthetic method of Ecteinascidin 743 . In 1996, E. J. Corey and his group developed a method and published it. At the same year, Ecteinascidin 743 was first dosed in humans. Now this product is prepared by a semisynthetic process developed by PharmaMar. The process begins from Safracin B. The antibiotic is obtained by fermentation of the bacterium Pseudomonas fluorescens.

 A lot of toxicity data has been done such as:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LDLo intravenous 75ug/kg (0.075mg/kg) LIVER: OTHER CHANGES
BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE		 Toxicologist. Vol. 42, Pg. 51, 1998.

  Now Ecteinascidin 743 is very available in the market under the brand name Yondelis provided by Zeltia and Johnson and Johnson. It is approved for the treatment of advanced soft tissue sarcoma in Europe, Russia and South Korea. It is also undergoing clinical trials for the treatment of breast, prostate, and paediatric sarcomas.

Flash Point: °C
Safety Data
 

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