An alkaloid with anticancer activity
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Trabectedin

Item No. 34662

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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-trimethyl-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
CAS Number
114899-77-3
Synonyms
  • Ecteinascidin 743
  • ET-743
  • NSC 648766
Molecular Formula
C39H43N3O11S
Formula Weight
761.8
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
SMILES
O[C@@H]([C@]1([H])CC2=CC(C)=C3OC)N([C@](COC4=O)([H])C5=C(OCO6)C6=C7C)[C@@]([C@@](N1C)([H])C2=C3O)([H])[C@@](SC[C@@]4(NCCC8=C9)C8=CC(OC)=C9O)([H])C5=C7OC(C)=O
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+/m0/s1
InChi Key
PKVRCIRHQMSYJX-AIFWHQITSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $213

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    1 mg

    $402

    Add
    Cayman Chemical
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    Product Description

    Trabectedin is an alkaloid that has been found in E. turbinata and has anticancer activity.1,2,3,4 It is a guanine-specific DNA alkylating agent and an antagonist of the pregnane X receptor (PXR; IC50 = ~3 nM in a reporter assay).1,2 Trabectedin reduces viability of DU145 and PC3 human prostate cancer stem cells in a concentration-dependent manner and induces apoptosis in DU145 and PC3 cancer stem cells and DU145 and PC3 non-stem cancer cells.3 It inhibits tumor growth in a patient-derived orthotopic xenograft (PDOX) mouse model of leiomyosarcoma when administered at a dose of 0.15 mg/kg per week.4 Formulations containing trabectedin have been used in the treatment of unresectable or metastatic liposarcoma or leiomyosarcoma.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pommier, Y., Kohlhagen, G., Bailly, C., et al. DNA sequence- and structure-selective alkylation of guanine N2 in the DNA minor groove by ecteinascidin 743, a potent antitumor compound from the Caribbean tunicate Ecteinascidia turbinata. Biochemistry 35(41), 13303-13309 (1996).

    2. Synold, T.W., Dussault, I., and Forman, B.M. The orphan nuclear receptor SXR coordinately regulates drug metabolism and efflux. Nat. Med. 7(5), 584-590 (2001).

    3. Acikgoz, E., Guven, U., Duzagac, F., et al. Enhanced G2/M arrest, caspase related apoptosis and reduced E-cadherin dependent intercellular adhesion by trabectedin in prostate cancer stem cells. PLoS One 10(10), e0141090 (2015).

    4. Zhang, Z., Hu, K., Kiyuna, T., et al. A patient-derived orthotopic xenograft (PDOX) nude-mouse model precisely identifies effective and ineffective therapies for recurrent leiomyosarcoma. Pharmacol. Res. 142, 169-175 (2019).