Eribulin Mesylate

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C40H59NO11.CH4O3S
Molecular Weight	826.002
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.[H][C@]12C[C@H]3O[C@H](C[C@@H](C)C3=C)CC[C@@H]4O[C@H](CC4=C)CC[C@@]56C[C@H]7O[C@H]8[C@@H](O5)[C@@]9([H])O[C@H](CC[C@]9([H])O[C@@]8([H])[C@H]7O6)CC(=O)C[C@@H]1[C@@H](OC)[C@@H](C[C@H](O)CN)O2

InChI

InChIKey=QAMYWGZHLCQOOJ-WRNBYXCMSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201532s016lbl.pdf | https://www.halaven.com/metastatic-breast-cancer

ERIBULIN MESYLATE (HALAVEN®) is a microtubule dynamics inhibitor. It is a synthetic analog of halichondrin B, a product isolated from the marine sponge Halichondria okadai. ERIBULIN MESYLATE (HALAVEN®) inhibits the growth phase of microtubules without affecting the shortening phase and sequesters tubulin into nonproductive aggregates. It 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 the prolonged mitotic blockage. ERIBULIN MESYLATE (HALAVEN®) is indicated for the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic disease. It is also indicated for the treatment of patients with unresectable or metastatic liposarcoma who have received a prior anthracycline-containing regimen.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin beta-1 chain 9 Target ID: Q9H4B7 Gene ID: 81027.0 Gene Symbol: TUBB1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16940412 \| https://www.drugbank.ca/drugs/DB08871 \| https://www.ncbi.nlm.nih.gov/pubmed/24665449	Inhibitor 8297		1.4 µM [IC50]
Apoptosis 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15313917	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast Cancer 3 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201532s016lbl.pdf	Primary		Approved 8429	HALAVEN Approved Use HALAVEN is a microtubule inhibitor indicated for the treatment of patients with: Metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic disease. Prior therapy should have included an anthracycline and a taxane in either the adjuvant or metastatic setting. (1.1) Unresectable or metastatic liposarcoma who have received a prior anthracycline-containing regimen. (1.2) 1.1 Me tastatic Breast Cancer HALAVEN is indicated for the treatment of patients with metastatic breast cancer who have previously received at least two chemotherapeutic regimens for the treatment of metastatic disease. Prior therapy should have included an anthracycline and a taxane in either the adjuvant or metastatic setting [see Clinical Studies (14.1) Launch Date 2010

C_max

Value	Dose	Co-administered	Analyte	Population
1213.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30679780	1.5 mg/m² 2 times / 4 weeks multiple, intravenous dose: 1.5 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		ERIBULIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
32364.4 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30679780	1.5 mg/m² 2 times / 4 weeks multiple, intravenous dose: 1.5 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		ERIBULIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
28.07 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30679780	1.5 mg/m² 2 times / 4 weeks multiple, intravenous dose: 1.5 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:		ERIBULIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
43% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/201532s010lbl.pdf			ERIBULIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1.4 mg/m2 2 times / 3 weeks steady, intravenous Recommended Dose: 1.4 mg/m2, 2 times / 3 weeks Route: intravenous Route: steady Dose: 1.4 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000MedR.pdf Page: p. 125	unhealthy, 55 years (range: 28 - 85 years) n = 508 Health Status: unhealthy Age Group: 55 years (range: 28 - 85 years) Sex: M+F Population Size: 508 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000MedR.pdf Page: p. 125	Disc. AE: Neurotoxicity, Elevated liver enzymes... AEs leading to discontinuation/dose reduction: Neurotoxicity (6%) Elevated liver enzymes (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000MedR.pdf Page: p. 125
1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	DLT: Fatigue, Anorexia... Other AEs: Vomiting, Nausea... Dose limiting toxicities: Fatigue (grade 3, 1 patient) Anorexia (grade 3, 1 patient) Other AEs: Vomiting (grade 3, 11%) Nausea (grade 1-2, 44%) Neutropenia (grade 1-2, 22%) Diarrhea (grade 1-2, 44%) Anemia (grade 1-2, 11%) Alopecia (grade 1-2, 11%) Stomatitis (grade 1-2, 22%) Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
0.5 mg/m2 3 times / 3 weeks multiple, intravenous Dose: 0.5 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 0.5 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 8 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	DLT: Fatigue... Dose limiting toxicities: Fatigue (grade 3, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
1.4 mg/m2 3 times / 3 weeks multiple, intravenous Dose: 1.4 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1.4 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	DLT: Neutropenia, Fatigue... Dose limiting toxicities: Neutropenia (grade 3-4, 2 patients) Fatigue (grade 3, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
1.4 mg/m2 2 times / 3 weeks steady, intravenous Recommended Dose: 1.4 mg/m2, 2 times / 3 weeks Route: intravenous Route: steady Dose: 1.4 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf	unhealthy, 58 years (range: 26 to 91 years) n = 503 Health Status: unhealthy Condition: multiple tumors Age Group: 58 years (range: 26 to 91 years) Sex: M+F Population Size: 503 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf	Disc. AE: Peripheral neuropathy, Neutropenia... AEs leading to discontinuation/dose reduction: Peripheral neuropathy (1%) Neutropenia (12%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf
2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	DLT: Febrile neutropenia, Oral candidiasis... Other AEs: Neutropenia, Leukopenia... Dose limiting toxicities: Febrile neutropenia (grade 4, 1 patient) Oral candidiasis (grade 2, 1 patient) Other AEs: Neutropenia (grade 3-4, 57%) Leukopenia (grade 1-2, 14%) Constipation (grade 1-2, 14%) Dry mouth (grade 1-2, 14%) Anorexia (grade 1-2, 29%) Fatigue (grade 1-2, 29%) Pyrexia (grade 1-2, 14%) Cough (grade 1-2, 14%) Alopecia (grade 1-2, 43%) Pruritic rash (grade 1-2, 14%) Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
2.8 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 2.8 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2.8 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 3 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	DLT: Febrile neutropenia... Dose limiting toxicities: Febrile neutropenia (grade 4, 2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
4 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 4 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 4 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 4 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	DLT: Febrile neutropenia... Dose limiting toxicities: Febrile neutropenia (grade 4, 3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
5.6 mg/m2 2 times / 3 weeks multiple, intravenous Overdose Dose: 5.6 mg/m2, 2 times / 3 weeks Route: intravenous Route: multiple Dose: 5.6 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf	Other AEs: Neutropenia, Hypersensitivity... Other AEs: Neutropenia (grade 3) Hypersensitivity (grade 3) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inducer 781 inhibitor 1587	inducer 389 inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP2E1 882 P-gp 1461	P-gp 1537	CYP1A 56 CYP2C19 293

Drug as perpetrator

Target	Modality	Activity
CYP1A 121	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94 Page: (ClinPharm) 68, 84, 94, 121	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94 Page: (ClinPharm) 68, 84, 94, 120	no
CYP2C19 1553	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94 Page: (ClinPharm) 68, 84, 94, 121	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94 Page: (ClinPharm) 68, 84, 94, 120	no
CYP2C9 1819	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94 Page: (ClinPharm) 68, 84, 94, 121	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94 Page: (ClinPharm) 68, 84, 94, 120	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68 Page: (ClinPharm) 68, 84, 120	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68 Page: (ClinPharm) 68, 84, 120	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68 Page: (ClinPharm) 68, 84, 121	no
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=122 Page: (ClinPharm) 68, 84, 94, 120, 122	weak [IC50 >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94 Page: (ClinPharm) 68, 84, 94, 120-121	yes [Ki 3 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000PharmR.pdf#page=21, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=122 Page: 21, 37-38, (ClinPharm) 68, 84, 94, 109-110, 119, 120, 122	major		unlikely (co-administration study) Comment: Human liver microsomes, CYP-mediated metabolism of eribulin appears to be minor.; Concomitant administration of ketoconazole, a CYP3A4 inhibitor, had no effect on exposure to eribulin (Dose-normalized AUC GM ratio: 0.95). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000PharmR.pdf#page=21, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=122 Page: 21, 37-38, (ClinPharm) 68, 84, 94, 109-110, 119, 120, 122
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=68, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=94, https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000ClinPharmR.pdf#page=121 Page: (ClinPharm) 68, 84, 94, 121	yes [Inhibition 0.002 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000PharmR.pdf#page=21 Page: 10, 21, 36

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:63587	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63587
ChemicalBook	CB22546700	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB22546700
ZINC	ZINC000169344691	http://zinc15.docking.org/substances/ZINC000169344691

PubMed

Title	Date	PubMed

Sample Use Guides

In Vivo Use Guide

Administer HALAVEN® 1.4 mg/m2 intravenously over 2 to 5 minutes on Days 1 and 8 of a 21-day cycle.

Route of Administration: Intravenous

Name

Type

Language

Eribulin Mesylate

Official Name

English

NSC-707389

Code

English

ERIBULIN MONOMETHANESULFONATE [MI]

Common Name

English

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,

Systematic Name

English

ERIBULIN MESYLATE [ORANGE BOOK]

Common Name

English

HALAVEN

Brand Name

English

ERIBULIN MESYLATE [VANDF]

Common Name

English

ERIBULIN MESILATE [MART.]

Common Name

English

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,

Systematic Name

English

Eribulin mesilate [WHO-DD]

Common Name

English

E-7389

Code

English

ERIBULIN (AS MESYLATE)

Common Name

English

ERIBULIN MESILATE [JAN]

Common Name

English

ERIBULIN MESYLATE [USAN]

Common Name

English

Eribulin Mesilate

Official Name

English

E7389

Code

English

ERIBULIN MONOMETHANESULFONATE

Common Name

English

ERIBULIN MESYLATE [EMA EPAR]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

367112

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

NCI_THESAURUS

C67422

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

Code System Code Type Description

PUBCHEM

17755248

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

PRIMARY

FDA UNII

AV9U0660CW

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

PRIMARY

SMS_ID

100000115485

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

PRIMARY

RXCUI

1045452

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

PRIMARY

RxNorm

NSC

707389

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

PRIMARY

USAN

RR-131

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

PRIMARY

CAS

441045-17-6

Created by admin on Fri Dec 15 16:29:15 GMT 2023 , Edited by admin on Fri Dec 15 16:29:15 GMT 2023

PRIMARY

DRUG BANK

DBSALT002427

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

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DAILYMED

AV9U0660CW

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

PRIMARY

NCI_THESAURUS

C26644

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

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CHEBI

70710

Created by admin on Fri Dec 15 16:29:15 GMT 2023 , Edited by admin on Fri Dec 15 16:29:15 GMT 2023

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MERCK INDEX

m4993

Created by admin on Fri Dec 15 16:29:16 GMT 2023 , Edited by admin on Fri Dec 15 16:29:16 GMT 2023

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Merck Index

ChEMBL

CHEMBL1683590

Created by admin on Fri Dec 15 16:29:15 GMT 2023 , Edited by admin on Fri Dec 15 16:29:15 GMT 2023

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EVMPD

SUB31126

Created by admin on Fri Dec 15 16:29:15 GMT 2023 , Edited by admin on Fri Dec 15 16:29:15 GMT 2023

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ACTIVE MOIETY


					LR24G6354G

Eribulin

SUBSTANCE RECORD


					AV9U0660CW

Eribulin Mesylate

AE	Significance	Dose	Population
Elevated liver enzymes	1% Disc. AE	1.4 mg/m2 2 times / 3 weeks steady, intravenous Recommended Dose: 1.4 mg/m2, 2 times / 3 weeks Route: intravenous Route: steady Dose: 1.4 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000MedR.pdf Page: p. 125	unhealthy, 55 years (range: 28 - 85 years) n = 508 Health Status: unhealthy Age Group: 55 years (range: 28 - 85 years) Sex: M+F Population Size: 508 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000MedR.pdf Page: p. 125
Neurotoxicity	6% Disc. AE	1.4 mg/m2 2 times / 3 weeks steady, intravenous Recommended Dose: 1.4 mg/m2, 2 times / 3 weeks Route: intravenous Route: steady Dose: 1.4 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000MedR.pdf Page: p. 125	unhealthy, 55 years (range: 28 - 85 years) n = 508 Health Status: unhealthy Age Group: 55 years (range: 28 - 85 years) Sex: M+F Population Size: 508 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201532Orig1s000MedR.pdf Page: p. 125
Alopecia	grade 1-2, 11%	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Anemia	grade 1-2, 11%	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Neutropenia	grade 1-2, 22%	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Stomatitis	grade 1-2, 22%	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Diarrhea	grade 1-2, 44%	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Nausea	grade 1-2, 44%	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Anorexia	grade 3, 1 patient DLT	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Fatigue	grade 3, 1 patient DLT	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Vomiting	grade 3, 11%	1 mg/m2 3 times / 3 weeks multiple, intravenous MTD Dose: 1 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Fatigue	grade 3, 1 patient DLT	0.5 mg/m2 3 times / 3 weeks multiple, intravenous Dose: 0.5 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 0.5 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 8 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Fatigue	grade 3, 1 patient DLT	1.4 mg/m2 3 times / 3 weeks multiple, intravenous Dose: 1.4 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1.4 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Neutropenia	grade 3-4, 2 patients DLT	1.4 mg/m2 3 times / 3 weeks multiple, intravenous Dose: 1.4 mg/m2, 3 times / 3 weeks Route: intravenous Route: multiple Dose: 1.4 mg/m2, 3 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509177	unhealthy, 57.4 years n = 9 Health Status: unhealthy Condition: Advanced Solid Malignancies Age Group: 57.4 years Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/19509177
Peripheral neuropathy	1% Disc. AE	1.4 mg/m2 2 times / 3 weeks steady, intravenous Recommended Dose: 1.4 mg/m2, 2 times / 3 weeks Route: intravenous Route: steady Dose: 1.4 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf	unhealthy, 58 years (range: 26 to 91 years) n = 503 Health Status: unhealthy Condition: multiple tumors Age Group: 58 years (range: 26 to 91 years) Sex: M+F Population Size: 503 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf
Neutropenia	12% Disc. AE	1.4 mg/m2 2 times / 3 weeks steady, intravenous Recommended Dose: 1.4 mg/m2, 2 times / 3 weeks Route: intravenous Route: steady Dose: 1.4 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf	unhealthy, 58 years (range: 26 to 91 years) n = 503 Health Status: unhealthy Condition: multiple tumors Age Group: 58 years (range: 26 to 91 years) Sex: M+F Population Size: 503 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf
Constipation	grade 1-2, 14%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Cough	grade 1-2, 14%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Dry mouth	grade 1-2, 14%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Leukopenia	grade 1-2, 14%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Pruritic rash	grade 1-2, 14%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Pyrexia	grade 1-2, 14%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Anorexia	grade 1-2, 29%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Fatigue	grade 1-2, 29%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Alopecia	grade 1-2, 43%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Oral candidiasis	grade 2, 1 patient DLT	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Neutropenia	grade 3-4, 57%	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Febrile neutropenia	grade 4, 1 patient DLT	2 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 2 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 7 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Febrile neutropenia	grade 4, 2 patients DLT	2.8 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 2.8 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 2.8 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 3 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 3 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Febrile neutropenia	grade 4, 3 patients DLT, Disc. AE	4 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 4 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 4 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/19509146	unhealthy, 62 yeras (range: 29-73 years) n = 4 Health Status: unhealthy Condition: advanced solid tumors Age Group: 62 yeras (range: 29-73 years) Sex: M+F Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/19509146
Hypersensitivity	grade 3	5.6 mg/m2 2 times / 3 weeks multiple, intravenous Overdose Dose: 5.6 mg/m2, 2 times / 3 weeks Route: intravenous Route: multiple Dose: 5.6 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf
Neutropenia	grade 3	5.6 mg/m2 2 times / 3 weeks multiple, intravenous Overdose Dose: 5.6 mg/m2, 2 times / 3 weeks Route: intravenous Route: multiple Dose: 5.6 mg/m2, 2 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/201532lbl.pdf

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201532s016lbl.pdf | https://www.halaven.com/metastatic-breast-cancer

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/201532s016lbl.pdf | https://www.halaven.com/metastatic-breast-cancer

C_max

T_1/2

F_unbound

Drug as perpetrator