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Éribuline

Éribuline
Image illustrative de l’article Éribuline
Identification
Nom UICPA 2-(3-amino-2-hydroxypropyl)hexacosahydro-3-méthoxy- 26-méthyl-20,27-bis(méthylène)11,15-18,21-24,28-triépoxy- 7,9-éthano-12,15-méthano-9H,15H-furo(3,2-i)furo(2',3'-5,6) pyrano(4,3-b)(1,4)dioxacyclopentacosin-5-(4H)-one
No CAS
No ECHA 100.230.372
Code ATC L01XX41
PubChem 17755248
SMILES
InChI
Propriétés chimiques
Formule C40H59NO11
Masse molaire[1] 729,896 6 ± 0,039 6 g/mol
C 65,82 %, H 8,15 %, N 1,92 %, O 24,11 %,

Unités du SI et CNTP, sauf indication contraire.

L'éribuline mesylate est un antinéoplasique fabriqué par le laboratoire Eisai Co.. C'est une cétone macrocyclique synthétique analogue du macrolide halichondrine B (en), isolée en 1986 à partir de l'éponge japonaise Halichondria okadai[2],[3].

Ce composé anticancéreux est autorisé depuis 2010 aux États-Unis dans le traitement du cancer du sein métastatique en troisième ligne[4].

Historique

Indications

Mécanisme d'action

L'érubiline est un inhibiteur du métabolisme des microtubules[5],[6].

Notes et références

  1. Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
  2. (en) Towle MJ, Salvato KA, Budrow J, Wels BF, Kuznetsov G, Aalfs KK, Welsh S, Zheng W, Seletsky BM, Palme MH, Habgood GJ, Singer LA, Dipietro LV, Wang Y, Chen JJ, Quincy DA, Davis A, Yoshimatsu K, Kishi Y, Yu MJ, Littlefield BA, « In vitro and in vivo anticancer activities of synthetic macrocyclic ketone analogues of halichondrin B », Cancer Res., vol. 61, no 3,‎ , p. 1013–21 (PMID 11221827)
  3. (en) Yu MJ, Kishi Y, Littlefield BA, Anticancer agents from natural products, Washington, DC, Taylor & Francis, (ISBN 0-8493-1863-7), « Discovery of E7389, a fully synthetic macrocyclic ketone analogue of halichondrin B »
  4. (en) « FDA approves new treatment option for late-stage breast cancer », USFDA, (consulté le )
  5. (en) Jordan MA, Kamath K, Manna T, Okouneva T, Miller HP, Davis C, Littlefield BA, Wilson L, « The primary antimitotic mechanism of action of the synthetic halichondrin E7389 is suppression of microtubule growth », Mol. Cancer Ther., vol. 4, no 7,‎ , p. 1086–95 (PMID 16020666, DOI 10.1158/1535-7163.MCT-04-0345)
  6. (en) Okouneva T, Azarenko O, Wilson L, Littlefield BA, Jordan MA, « Inhibition of Centromere Dynamics by Eribulin (E7389) during Mitotic Metaphase », Mol. Cancer Ther., vol. 7, no 7,‎ , p. 2003–11 (PMID 18645010, PMCID 2562299, DOI 10.1158/1535-7163.MCT-08-0095)
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Éribuline
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