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Eribulin mesylate

Eribulin mesylate structure

CAS No:
441045-17-6
Formula:
C40H59NO11.CH4O3S
Chemical Name:
Eribulin mesylate
Synonyms:
11,15:18,21:24,28-Triepoxy-7,9-ethano-12,15-methano-9H,15H-furo[3,2-i]furo[2′,3′:5,6]pyrano[4,3-b][1,4]dioxacyclopentacosin-5(4H)-one,2-[(2S)-3-amino-2-hydroxypropyl]hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)-,(2R,3R,3aS,7R,8aS,9S,10aR,11S,12R,13aR,13bS,15S,18S,21S,24S,26R,28R,29aS)-,methanesulfonate (1:1);11,15:18,21:24,28-Triepoxy-7,9-ethano-12,15-methano-9H,15H-furo[3,2-i]furo[2′,3′:5,6]pyrano[4,3-b][1,4]dioxacyclopentacosin-5(4H)-one,2-[(2S)-3-amino-2-hydroxypropyl]hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)-,(2R,3R,3aS,7R,8aS,9S,10aR,11S,12R,13aR,13bS,15S,18S,21S,24S,26R,28R,29aS)-,methanesulfonate (salt);Eribulin mesylate;E 7389 methanesulfonate;Halaven
Categories:
Specialty Chemicals

Description

Eribulin mesylate is a microtubule targeting agent that is used in the treatment of metastatic breast cancer. It inhibits the proliferation of cancer cells by binding microtubule proteins and microtubules.

Eribulin mesylate is a methanesulfonate salt obtained by reaction of eribulin with one equivalent of methanesulfonic acid. A fully synthetic macrocyclic ketone analogue of marine sponge natural products. Inhibits growth phase of microtubules via tubulin-based antimitotic mechanism, which leads to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage. It has a role as an antineoplastic agent and a microtubule-destabilising agent. It contains an eribulin(1+).|Eribulin Mesylate is the mesylate salt of a synthetic analogue of halichondrin B, a substance derived from a marine sponge (Lissodendoryx sp.) with antineoplastic activity. Eribulin binds to the vinca domain of tubulin and inhibits the polymerization of tubulin and the assembly of microtubules, resulting in inhibition of mitotic spindle assembly, induction of cell cycle arrest at G2/M phase, and, potentially, tumor regression.

Eribulin mesylate Basic Attributes

Molecular Weight：

826 g/mol

Exact Mass：

825.396912

EC Number：

-0

UNII：

AV9U0660CW

NCI Thesaurus Code：

C26644

ATC Code：

L01XX41

Characteristics

PSA：

209.14000

XLogP3：

4.72310

Safety Information

GHS Classification：

|Warning|H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

Drug Indication：

Halaven monotherapy is indicated for the treatment of patients with locally advanced or metastatic breast cancer who have progressed after at least one chemotherapeutic regimens for advanced disease (see section 5.1). Prior therapy should have included an anthracycline and a taxane unless patients were not suitable for these treatments.Halaven is indicated for the treatment of adult patients with unresectable liposarcoma who have received prior anthracycline containing therapy (unless unsuitable) for advanced or metastatic disease (see section 5.1).|Drug: Eribulinmesylate

MeSH Entry Terms：

B 1793

Eribulin mesylate Use and Manufacturing

Use Classification：

Human drugs -> Halaven -> EMA Drug Category|Antineoplastic agents -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:826.0
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:4
Exact Mass:825.39692686
Monoisotopic Mass:825.39692686
Topological Polar Surface Area:209
Heavy Atom Count:57
Complexity:1470
Defined Atom Stereocenter Count:19
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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