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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H55NO8
Molecular Weight 593.793
Optical Activity UNSPECIFIED
Defined Stereocenters 13 / 13
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of DISERMOLIDE

SMILES

C=C/C(/[H])=C(/[H])\[C@]([H])(C)[C@@]([H])([C@@]([H])(C)[C@@]([H])([C@@]([H])(C)C/C(=C(/[H])\[C@]([H])(C)[C@]([H])([C@@]([H])(C)/C(/[H])=C(/[H])\[C@]([H])(C[C@@]1([H])[C@]([H])(C)[C@@]([H])([C@@]([H])(C)C(=O)O1)O)O)O)/C)O)OC(=N)O

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

HIDE SMILES / InChI

Molecular Formula C33H55NO8
Molecular Weight 593.793
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 3
Optical Activity UNSPECIFIED

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

PubMed

TitleDatePubMed
Synthesis of (+)-discodermolide by catalytic stereoselective borylation reactions.
2014 Sep 1
Induction of accelerated senescence by the microtubule-stabilizing agent peloruside A.
2017 Dec
Structural Basis of Microtubule Stabilization by Discodermolide.
2017 May 18
Improved Dose-Response Relationship of (+)-Discodermolide-Taxol Hybrid Congeners.
2018 Mar 23
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:41:40 UTC 2021
Edited
by admin
on Sat Jun 26 16:41:40 UTC 2021
Record UNII
DHG59994DN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DISERMOLIDE
INN  
INN  
Official Name English
DISCODERMOLIDE [MI]
Common Name English
DISCODERMOLIDE
MI  
Common Name English
DISERMOLIDE [INN]
Common Name English
XAA-296
Code English
(+)-DISCODERMOLIDE
Common Name English
XAA 296
Code English
2H-PYRAN-2-ONE, 6-((2S,3Z,5S,6S,7S,8Z,11S,12R,13S,14S,15S,16Z)-14-((AMINOCARBONYL)OXY)-2,6,12-TRIHYDROXY-5,7,9,11,13,15-HEXAMETHYL-3,8,16,18-NONADECATETRAEN-1-YL)TETRAHYDRO-4-HYDROXY-3,5-DIMETHYL-, (3R,4S,5R,6S)-
Common Name English
(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-TRIHYDROXY-19-((2S,3R,4S,5R)-4-HYDROXY-3,5-DIMETHYL-6-OXOTETRAHYDRO-2H-PYRAN-2-YL)-5,7,9,11,13,15-HEXAMETHYLNONADECA-1,3,11,16-TETRAEN-6-YL CARBAMATE
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL364447
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY
CAS
127943-53-7
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY
WIKIPEDIA
DISCODERMOLIDE
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY
MERCK INDEX
M4667
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY Merck Index
PUBCHEM
643668
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY
NCI_THESAURUS
C169917
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY
INN
8389
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY
MESH
C071229
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY
FDA UNII
DHG59994DN
Created by admin on Sat Jun 26 16:41:40 UTC 2021 , Edited by admin on Sat Jun 26 16:41:40 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY