253128-41-5 Usage
Description
Eribulin, also known as eribulin mesylate or E7389, is a fully synthetic macrocyclic ketone analogue of the marine natural product halichondrin B, isolated from the sea sponge Halichondria okadai. It is a microtubule inhibitor that binds close to the vinca-binding site of tubulin, exhibiting unique effects on microtubule dynamic instability by inhibiting the growth phase of microtubules without affecting the shortening phase. Eribulin has a role as an antineoplastic agent and a microtubule-destabilizing agent, and is classified as a macrocycle, polyether, polycyclic ether, cyclic ketone, primary amino compound, and cyclic ketal. It is a conjugate base of an eribulin(1+) and is marketed under the brand name Halaven.
Uses
Used in Oncology:
Eribulin is used as an anticancer drug for the treatment of metastatic breast cancer (MBC) in patients who have previously received at least two chemotherapeutic regimens for late-stage disease. It is a synthetic analog of halichondrin B, which is derived from a marine sponge (Lissodendoryx sp.) and possesses antineoplastic activity.
Eribulin is used as a microtubule inhibitor for its unique mechanism of action, which involves binding to microtubule plus ends and inhibiting the growth phase of microtubules. This leads to a G2/M cell-cycle block, disruption of mitotic spindles, and ultimately, apoptotic cell death after prolonged mitotic blockage. Its distinct mode of action differentiates it from other tubulin inhibitors like taxanes, epothilones, and vinca alkaloids.
Originator
Eisai (United States)
Clinical Use
Antineoplastic agent:Treatment of metastatic breast cancer
Drug interactions
Potentially hazardous interactions with other drugs
Antipsychotics: avoid concomitant use with
clozapine (increased risk of agranulocytosis).
Metabolism
Minimal metabolism. Eribulin is eliminated primarily
by biliary excretion. The transport protein involved in
the excretion is presently unknown. Preclinical studies
indicate that eribulin is transported by Pgp. However,
it is unknown whether Pgp is contributing to the biliary
excretion of eribulin.
Mode of action
Eribulin is a non-taxane, microtubule dynamics inhibitor that increases survival of patients with metastatic breast cancer. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 253128-41-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,5,3,1,2 and 8 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 253128-41:
(8*2)+(7*5)+(6*3)+(5*1)+(4*2)+(3*8)+(2*4)+(1*1)=115
115 % 10 = 5
So 253128-41-5 is a valid CAS Registry Number.
253128-41-5Relevant articles and documents
PROCESS FOR THE PREPARATION OF ERIBULIN MESYLATE INTERMEDIATE
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Paragraph 0025, (2021/02/12)
The present application provides improved processes for the synthesis of eribulin intermediate, which generally comprise the steps of: a) De-protecting the eribulin-enone (compound 1) in tetrahydrofuran by using TBAF solution, buffered with imidazole HCl in the presence of molecular sieve and sodium sulphate to get an insitu mixture of eribulin-dione diastereomer at C12 carbon (compound 2). Then ketalization may be performed of eribulin-dione insitu intermediate containing mixture of diastereomer at C12 carbon (compound 2) with PPTS in dichloromethane to yield eribulin-diol (compound 3).
PROCESS FOR PREPARATION OF ERIBULIN AND INTERMEDIATES THEREOF
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, (2020/05/19)
The present application relate to crystalline azide compound of formula (II) which is used as an intermediate for the preparation of halichondrin B analogues such as eribulin or pharmaceutically acceptable salts thereof. The present application also covers purification process of azide compound of formula (II) and its further conversion to eribulin or a pharmaceutically acceptable salts thereof.
Intermediate for preparing Eribulin and preparation method thereof
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Paragraph 0217; 0218; 0220; 0221; 0239, (2019/05/11)
The invention relates to an intermediate for preparing Eribulin and a preparation method of the intermediate. Specifically, the method comprises the following steps: selectively removing 1,2-hydroxylprotecting groups, so that the 1,2-hydroxyl structure is selectively converted; the whole process steps are simple, the operation is simple and convenient, and the method is suitable for industrial mass production requirements.
