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    Eribulin

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Halaven, Eribulin mesilate, 441045-17-6, Eribulin (mesylate), Eribulin mesylate [usan], Eribulin (as mesylate)
    Molecular Formula
    C41H63NO14S
    Molecular Weight
    826.0  g/mol
    InChI Key
    QAMYWGZHLCQOOJ-WRNBYXCMSA-N
    FDA UNII
    AV9U0660CW
    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.
    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;methanesulfonic acid
    2.1.2 InChI
    InChI=1S/C40H59NO11.CH4O3S/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;1-5(2,3)4/h19,23-39,43H,2-3,5-18,41H2,1,4H3;1H3,(H,2,3,4)/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
    QAMYWGZHLCQOOJ-WRNBYXCMSA-N
    2.1.4 Canonical SMILES
    CC1CC2CCC3C(=C)CC(O3)CCC45CC6C(O4)C7C(O6)C(O5)C8C(O7)CCC(O8)CC(=O)CC9C(CC(C1=C)O2)OC(C9OC)CC(CN)O.CS(=O)(=O)O
    2.1.5 Isomeric SMILES
    C[C@@H]1C[C@@H]2CC[C@H]3C(=C)C[C@@H](O3)CC[C@]45C[C@@H]6[C@H](O4)[C@H]7[C@@H](O6)[C@@H](O5)[C@@H]8[C@@H](O7)CC[C@@H](O8)CC(=O)C[C@H]9[C@H](C[C@H](C1=C)O2)O[C@@H]([C@@H]9OC)C[C@@H](CN)O.CS(=O)(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    AV9U0660CW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. B 1793

    2. B 1939

    3. B-1793

    4. B-1939

    5. E 7389

    6. E-7389

    7. Er 086526

    8. Er-086526

    9. Er-86526

    10. Er086526

    11. Eribulin

    12. Eribulin (as Mesylate)

    13. Eribulin Mesilate

    14. Eribulin Monomethanesulfonate

    15. Halaven

    16. Nsc 707389

    17. Nsc-707389

    18. Nsc707389

    2.3.2 Depositor-Supplied Synonyms

    1. Halaven

    2. Eribulin Mesilate

    3. 441045-17-6

    4. Eribulin (mesylate)

    5. Eribulin Mesylate [usan]

    6. Eribulin (as Mesylate)

    7. E7389

    8. Eribulin Monomethanesulfonate

    9. Av9u0660cw

    10. Chebi:70710

    11. E 7389

    12. E-7389

    13. Eribulin Mesilate (jan)

    14. Eribulin Mesylate (usan)

    15. B-1939

    16. (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;methanesulfonic Acid

    17. Eribulin Mesilate [jan]

    18. Nsc-707389

    19. Er-086526

    20. Unii-av9u0660cw

    21. Halaven (tn)

    22. B1939 Mesylate

    23. E7389 Mesylate

    24. Er-086526 Mesylate

    25. Chembl1683544

    26. Eribulin Mesylate [vandf]

    27. Eribulin Mesilate [mart.]

    28. Eribulin Mesilate [who-dd]

    29. Ex-a4873

    30. Eribulin Mesylate [ema Epar]

    31. Hy-13442a

    32. Eribulin Mesylate [orange Book]

    33. Eribulin Monomethanesulfonate [mi]

    34. D08914

    35. Q27882076

    36. B1939 Mesylate; E7389 Mesylate; Er-086526 Mesylate

    37. (2r,3r,3as,7r,8as,9s,10ar,11s,12r,13ar,13bs,15s,18s,21s,24s,26r,28r,29as)-2-((2s)-3-amino-2-hydroxypropyl)-3-methoxy-26-methyl-20,27-dimethylidenehexacosahydro-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 Methanesulfonate (salt)

    38. 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)

    39. 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 Methanesulfonate

    2.4 Create Date
    2007-11-26
    3 Chemical and Physical Properties
    Molecular Weight 826.0 g/mol
    Molecular Formula C41H63NO14S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count4
    Exact Mass825.39692686 g/mol
    Monoisotopic Mass825.39692686 g/mol
    Topological Polar Surface Area209 Ų
    Heavy Atom Count57
    Formal Charge0
    Complexity1470
    Isotope Atom Count0
    Defined Atom Stereocenter Count19
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameHalaven
    PubMed HealthEribulin (Injection)
    Drug ClassesAntineoplastic Agent
    Drug LabelHALAVEN (eribulin mesylate) Injection is a non-taxane microtubule dynamics inhibitor. Eribulin mesylate is a synthetic analogue of halichondrin B, a product isolated from the marine sponge Halichondria okadai. The chemical name for eribulin mesyl...
    Active IngredientEribulin mesylate
    Dosage FormSolution
    RouteIntravenous
    Strength1mg/2ml (0.5mg/ml)
    Market StatusPrescription
    CompanyEisai

    2 of 2  
    Drug NameHalaven
    PubMed HealthEribulin (Injection)
    Drug ClassesAntineoplastic Agent
    Drug LabelHALAVEN (eribulin mesylate) Injection is a non-taxane microtubule dynamics inhibitor. Eribulin mesylate is a synthetic analogue of halichondrin B, a product isolated from the marine sponge Halichondria okadai. The chemical name for eribulin mesyl...
    Active IngredientEribulin mesylate
    Dosage FormSolution
    RouteIntravenous
    Strength1mg/2ml (0.5mg/ml)
    Market StatusPrescription
    CompanyEisai

    4.2 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).

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Pharmacological Classes
    Microtubule Inhibitor [EPC]; Microtubule Inhibition [PE]
    5.2 ATC Code

    L01XX41