U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of Eribulin Mesylate

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
Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C40H59NO11
Molecular Weight 729.8966
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

2010
465
Targets

Targets

Primary TargetPharmacologyConditionPotency
Tubulin beta-1 chain
9
Target ID: Q9H4B7
Gene ID: 81027.0
Gene Symbol: TUBB1
Target Organism: Homo sapiens (Human)
Inhibitor
8297
 1.4 µM [IC50]
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

1.28977915E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inducer
781

inhibitor
1587
inducer
389

inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C19
1478

CYP2E1
882

P-gp
1461
P-gp
1537
CYP1A
56

CYP2C19
293
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
121
 no
CYP1A2
1692
 no
CYP2C19
1553
 no
CYP2C19
1553
 no
CYP2C9
1819
 no
CYP2C9
1819
 no
CYP2D6
1891
 no
CYP2E1
970
 no
CYP3A4
1925
 no
P-gp
1650
 weak [IC50 >10 uM]
CYP3A4
1925
 yes [Ki 3 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1737
 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).
Page: 21, 37-38, (ClinPharm) 68, 84, 94, 109-110, 119, 120, 122
P-gp
1537
 yes [Inhibition 0.002 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:29:15 UTC 2023
Edited
by admin
on Fri Dec 15 16:29:15 UTC 2023
Record UNII
AV9U0660CW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Eribulin Mesylate
DASH   EMA EPAR   ORANGE BOOK   USAN   VANDF  
USAN  
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
JAN   MART.   WHO-DD  
JAN  
Official Name English
E7389
Code English
ERIBULIN MONOMETHANESULFONATE
MI  
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 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
NCI_THESAURUS C67422
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
Code System Code Type Description
PUBCHEM
17755248
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY
FDA UNII
AV9U0660CW
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY
SMS_ID
100000115485
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY
RXCUI
1045452
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY RxNorm
NSC
707389
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY
USAN
RR-131
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY
CAS
441045-17-6
Created by admin on Fri Dec 15 16:29:15 UTC 2023 , Edited by admin on Fri Dec 15 16:29:15 UTC 2023
PRIMARY
DRUG BANK
DBSALT002427
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY
DAILYMED
AV9U0660CW
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY
NCI_THESAURUS
C26644
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY
CHEBI
70710
Created by admin on Fri Dec 15 16:29:15 UTC 2023 , Edited by admin on Fri Dec 15 16:29:15 UTC 2023
PRIMARY
MERCK INDEX
m4993
Created by admin on Fri Dec 15 16:29:16 UTC 2023 , Edited by admin on Fri Dec 15 16:29:16 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1683590
Created by admin on Fri Dec 15 16:29:15 UTC 2023 , Edited by admin on Fri Dec 15 16:29:15 UTC 2023
PRIMARY
EVMPD
SUB31126
Created by admin on Fri Dec 15 16:29:15 UTC 2023 , Edited by admin on Fri Dec 15 16:29:15 UTC 2023
PRIMARY
Related Record Type Details
Structure of Eribulin
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of Eribulin
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966