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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
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 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


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C-24,INDUSTRIAL HYDERABAD"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q4","strtotime":1668796200,"product":"ERIBULIN INTERMEDIATE N-6 [121 GMS]","address":"T-184, MIDC, BHOSARI,,PUNE","city":"PUNE,MAHARASHTRA","supplier":"ZENJI RESEARCH LABORATORIES","supplierCountry":"CHINA","foreign_port":"NA","customer":"EMCURE PHARMACEUTICALS","customerCountry":"INDIA","quantity":"0.12","actualQuantity":"0.121","unit":"KGS","unitRateFc":"3500000","totalValueFC":"428623.4","currency":"USD","unitRateINR":"289100000","date":"19-Nov-2022","totalValueINR":"34981100","totalValueInUsd":"428623.4","indian_port":"BOMBAY AIR","hs_no":"29321990","bill_no":"3377288","productDescription":"Intermediate","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"T-184, MIDC, BHOSARI,,PUNE"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1702665000,"product":"ERIBULIN INTERMEDIATE N-6 [3 GMS]","address":"T-184, MIDC, BHOSARI,","city":"PUNE-MAHARASHTRA","supplier":"PHARMACEUTICAL TECHNOLOGY","supplierCountry":"CHINA","foreign_port":"SHANGHAI - PU DONG","customer":"EMCURE PHARMACEUTICALS","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.003","unit":"KGS","unitRateFc":"2250000","totalValueFC":"6835.7","currency":"USD","unitRateINR":"189675000","date":"16-Dec-2023","totalValueINR":"569025","totalValueInUsd":"6835.7","indian_port":"Bombay Air","hs_no":"29321990","bill_no":"9255871","productDescription":"Intermediate","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI - PU DONG","supplierAddress":"PUDONG NEW AREA BUILDING 22, NO.8666,SHANGHAI 201300 Shanghai, , ChinaSDNF China","customerAddress":"T-184, MIDC, BHOSARI,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1704997800,"product":"ERIBULIN MESYLATE","address":"101, SITARAM MANSION,","city":"KAROL BAGH, NEW DELHI","supplier":"BRIGHTGENE BIO-MEDICAL TECHNOLOGY CO.,LTD","supplierCountry":"CHINA","foreign_port":"SHANGHAI - PU DONG","customer":"JODAS EXPOIM PVT. 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AP","supplier":"MILVERPHARMA PVT LTD","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"MSN LABORATORIES","customerCountry":"INDIA","quantity":"0.05","actualQuantity":"0.05","unit":"KGS","unitRateFc":"1650000","totalValueFC":"83332.5","currency":"USD","unitRateINR":"139177500","date":"15-Apr-2024","totalValueINR":"6958875","totalValueInUsd":"83332.5","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"3030786","productDescription":"Intermediate","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"9TH FLOOR,1#,NO.98 CHUANGYUAN RD,HI-TECH ZONE NINGBO CHINA 315040SDNF CN","customerAddress":"MSN HOUSE, PLOT NO. C-24,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1726425000,"product":"ERIBULIN INTERMEDIATE N-6 (0.0001 KGS)","address":"T-184, MIDC, BHOSARI,","city":"PUNE-MAHARASHTRA","supplier":"PHARMACEUTICAL TECHNOLOGY","supplierCountry":"CHINA","foreign_port":"SHANGHAI - PU DONG","customer":"EMCURE PHARMACEUTICALS","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.0001","unit":"KGS","unitRateFc":"6000000","totalValueFC":"607.9","currency":"USD","unitRateINR":"509400000","date":"16-Sep-2024","totalValueINR":"50940","totalValueInUsd":"607.9","indian_port":"Bombay Air","hs_no":"29321990","bill_no":"5629119","productDescription":"Intermediate","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI - PU DONG","supplierAddress":"BUILDING 22 , NO.8666,HUNAN HIGHWAY , PUDONG NEW DISTRICT SHANGHAI, P.R .CHINA 201314 Shanghai, , China China","customerAddress":"T-184, MIDC, BHOSARI,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1728412200,"product":"ERIBULIN MESYLATE","address":"H.NO. 8-2-337,BESIDE TV9 OFFICE","city":"HYDERABAD ANDHRA PRADESH","supplier":"DR. REDDY\\'S LABORATORIES","supplierCountry":"INDIA","foreign_port":"VISAKHAPATNAM SEZ","customer":"DR. REDDY\\'S LABORATORIES","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"2.753","unit":"GMS","unitRateFc":"44686.3","totalValueFC":"124227","currency":"USD","unitRateINR":"3791634","date":"09-Oct-2024","totalValueINR":"10438368.4","totalValueInUsd":"124227","indian_port":"Vizag-EPZ\/SEZ","hs_no":"29339990","bill_no":"6025491","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"VISAKHAPATNAM SEZ","supplierAddress":"FTO -7, PLOT NO.P1 TO P9 V.S.E.Z., DUVVADA, VISAKHAPATNAM SDNF India","customerAddress":"H.NO. 8-2-337,BESIDE TV9 OFFICE"}]
18-Jan-2021
09-Oct-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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US Patents

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American Pharma Summit
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EISAI INC

U.S.A
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ERIBULIN MESYLATE

US Patent Number : RE46965*PED

Drug Substance Claim :

Drug Product Claim :

Application Number : 201532

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2027-07-08

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American Pharma Summit
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EISAI INC

U.S.A
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American Pharma Summit
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ERIBULIN MESYLATE

US Patent Number : 6214865*PED

Drug Substance Claim :

Drug Product Claim :

Application Number : 201532

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2024-01-20

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American Pharma Summit
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EISAI INC

U.S.A
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American Pharma Summit
Not Confirmed

ERIBULIN MESYLATE

US Patent Number : RE46965

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 201532

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2027-01-08

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euroPLX 86 Munich
Not Confirmed

EISAI INC

U.S.A
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euroPLX 86 Munich
Not Confirmed

ERIBULIN MESYLATE

Exclusivity Code : M-280

Exclusivity Expiration Date : 2025-09-13

Application Number : 201532

Product Number : 1

Exclusivity Details :

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EISAI INC

U.S.A
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euroPLX 86 Munich
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ERIBULIN MESYLATE

Exclusivity Code : PED

Exclusivity Expiration Date : 2026-03-13

Application Number : 201532

Product Number : 1

Exclusivity Details :

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Health Canada Patents

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01

Torys LLP

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euroPLX 86 Munich
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Torys LLP

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Eribulin

Brand Name : HALAVEN

Patent Number : 2335300

Filing Date : 1999-06-16

Strength per Unit : 0.5 mg / mL

Dosage Form : Solution for injection

Human Or VET : Human

Route of Administration : Intravenous

Patent Expiration Date : 2019-06-16

Date Granted : 2008-10-07

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