Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H55NO8 |
Molecular Weight | 593.7917 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 3 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H](C\C(C)=C/[C@H](C)[C@@H](O)[C@@H](C)\C=C/[C@@H](O)C[C@@H]1OC(=O)[C@H](C)[C@@H](O)[C@H]1C)[C@@H](O)[C@H](C)[C@@H](OC(N)=O)[C@@H](C)\C=C/C=C
InChI
InChIKey=AADVCYNFEREWOS-OBRABYBLSA-N
InChI=1S/C33H55NO8/c1-10-11-12-20(4)31(42-33(34)40)24(8)29(37)22(6)16-18(2)15-21(5)28(36)19(3)13-14-26(35)17-27-23(7)30(38)25(9)32(39)41-27/h10-15,19-31,35-38H,1,16-17H2,2-9H3,(H2,34,40)/b12-11-,14-13-,18-15-/t19-,20-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30-,31-/m0/s1
Disermolide (discodermolide) is the immunosuppressant and antineoplastic agent. The marine natural product discodermolide was first isolated in 1990 from the deep-water Caribbean sponge Discodermia dissoluta. It attacks cancer cells in a similar way to the successful cancer drug Taxol that has become the best-selling anticancer drug in history. Discodermolide is a microtubule-stabilizing agent with potential for the treatment of taxol-refractory malignancies. Discodermolide is a drug that functions as an immunosuppressant and induces G2/M phase cell-cycle arrest in lymphoid and non-lymphoid cells. The cytotoxicity of discodermolide cause cell-cycle arrest by mitosis and an important alteration at the level of microtubules. Discodermolide is a potent inducer of accelerated senescence. At present, Phase I trials with discodermolide has been discontinued as a consequence of unsafe efficacy and toxicity results.
Approval Year
PubMed
Title | Date | PubMed |
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Design and synthesis of (+)-discodermolide-paclitaxel hybrids leading to enhanced biological activity. | 2011 Sep 22 |
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Mariculture and natural production of the antitumoural (+)-discodermolide by the Caribbean marine sponge Discodermia dissoluta. | 2013 Oct |
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Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions. | 2014 Sep 1 |
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Structural Basis of Microtubule Stabilization by Discodermolide. | 2017 May 18 |
Patents
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CHEMBL364447
Created by
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127943-53-7
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DISCODERMOLIDE
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m4667
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643668
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C169917
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8389
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C071229
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DHG59994DN
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DTXSID40893493
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300000034196
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ACTIVE MOIETY