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Eribulin

Synopsis, Chemistry

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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

Eribulin

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 Formula	C₄₁H₆₃NO₁₄S
Molecular Weight	826.0 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	4
Exact Mass	825.39692686 g/mol
Monoisotopic Mass	825.39692686 g/mol
Topological Polar Surface Area	209 Å²
Heavy Atom Count	57
Formal Charge	0
Complexity	1470
Isotope Atom Count	0
Defined Atom Stereocenter Count	19
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Halaven
PubMed Health	Eribulin (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	HALAVEN (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 Ingredient	Eribulin mesylate
Dosage Form	Solution
Route	Intravenous
Strength	1mg/2ml (0.5mg/ml)
Market Status	Prescription
Company	Eisai

2 of 2
Drug Name	Halaven
PubMed Health	Eribulin (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	HALAVEN (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 Ingredient	Eribulin mesylate
Dosage Form	Solution
Route	Intravenous
Strength	1mg/2ml (0.5mg/ml)
Market Status	Prescription
Company	Eisai

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