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    CAS 253128-41-5

    BUILDING BLOCK

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 253128-41-5, Eribuline, Eribulina, Chebi:63587, Er 086526, E-7389 free base
    Molecular Formula
    C40H59NO11
    Molecular Weight
    729.9  g/mol
    InChI Key
    UFNVPOGXISZXJD-JBQZKEIOSA-N
    FDA UNII
    LR24G6354G
    a halichondrin B derivative that suppresses microtubule growth and acts as an antimitotic agent; structure in first source
    Eribulin is a Microtubule Inhibitor. The physiologic effect of eribulin is by means of Microtubule Inhibition.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33R,35R,36S)-20-[(2S)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one
    2.1.2 InChI
    InChI=1S/C40H59NO11/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
    2.1.3 InChI Key
    UFNVPOGXISZXJD-JBQZKEIOSA-N
    2.2 Other Identifiers
    2.2.1 UNII
    LR24G6354G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(3-amino-2-hydroxypropyl)hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)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

    2.3.2 Depositor-Supplied Synonyms

    1. 253128-41-5

    2. Eribuline

    3. Eribulina

    4. Chebi:63587

    5. Er 086526

    6. E-7389 Free Base

    7. Lr24g6354g

    8. 2-(3-amino-2-hydroxypropyl)hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)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

    9. Dtxsid101009321

    10. Nsc-707389

    11. B-1939

    12. Eribulinum

    13. L01xx41

    14. Dtxcid701436148

    15. Er-86526

    16. Er086526

    17. Eribulin [inn]

    18. (1s,3s,6s,9s,12s,14r,16r,18s,20r,21r,22s,26r,29s,31r,32s,33r,35r,36s)-20-[(2s)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one

    19. Er-086526

    20. (2r,3r,3as,7r,8as,9s,10ar,11s,12r,13ar,13bs,15s,18s,21s,24s,26r,28r,29as)-2-[(2s)-3-amino-2-hydroxypropyl]hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)-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

    21. (1s,3s,6s,9s,12s,14r,16r,18s,20r,21r,22s,26r,29s,31r,32s,35r,36s)-20-[(2s)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1(3,32).1(3,33).1(6,9).1(12,16).0(18,22).0(29,36).0(31,35)]hentetracontan-24-one

    22. Eribulin Free

    23. Unii-lr24g6354g

    24. (1s,3s,6s,9s,12s,14r,16r,18s,20r,21r,22s,26r,29s,31r,32s,33r,35r,36s)-20-[(2s)-3-amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylidene-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.1~3,32~.1~3,33~.1~6,9~.1~12,16~.0~18,22~.0~29,36~.0~31,35~]hentetracontan-24-one (non-preferred Name)

    25. Eribulin [mi]

    26. Eribulin [vandf]

    27. Eribulin [mart.]

    28. Eribulin [who-dd]

    29. B 1939

    30. E7389-lf

    31. Gtpl6813

    32. Orb1707961

    33. Chembl1683590

    34. Schembl15783821

    35. Ex-a4873d

    36. Ufnvpogxiszxjd-jbqzkeiosa-n

    37. Glxc-10730

    38. Akos040740784

    39. At36513

    40. Db08871

    41. Ncgc00510497-02

    42. Bp-29357

    43. Da-52974

    44. Hy-13442

    45. Ms-31267

    46. Q408717

    47. 2-[4-[[(2r)-2-aminobutyl]amino]-2-quinazolinyl]-4-chloro-phenol

    48. 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)-

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 729.9 g/mol
    Molecular Formula C40H59NO11
    XLogP31.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count4
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area146
    Heavy Atom Count52
    Formal Charge0
    Complexity1380
    Isotope Atom Count0
    Defined Atom Stereocenter Count19
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic cancer.

    FDA Label

    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).

    Treatment of soft tissue sarcoma

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Active Moiety
    ERIBULIN
    5.1.2 FDA UNII
    LR24G6354G
    5.1.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Microtubule Inhibitor
    5.2 ATC Code

    L01XX41

    L01XX41

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (2021) DOI:10.1021/acsenvironau.1c00008. List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01X - Other antineoplastic agents

    L01XX - Other antineoplastic agents

    L01XX41 - Eribulin

    5.3 Absorption, Distribution and Excretion

    Route of Elimination

    Eribulin is eliminated primarily in feces unchanged.

    Volume of Distribution

    43 L/m2 to 114 L/m2

    Clearance

    1.16 L/hr/m2 to 2.42 L/hr/m2 (dose range of 0.25 mg/m2 to 4.0 mg/m2). [FDA]

    5.4 Metabolism/Metabolites

    There are no major human metabolites of eribulin, CYP3A4 negligibly metabolizes eribulin in vitro.

    5.5 Biological Half-Life

    about 40 hours

    5.6 Mechanism of Action

    Eribulin inhibits the growth phase of microtubules without affecting the shortening phase and sequesters tubulin into nonproductive aggregates. Eribulin exerts its effects via a tubulin-based antimitotic mechanism leading to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage. [FDA]