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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H42N2O5S
Molecular Weight 506.698
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of IXABEPILONE

SMILES

C[C@H]1CCC[C@@]2(C)O[C@H]2C[C@H](NC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(\C)=C\C3=CSC(C)=N3

InChI

InChIKey=FABUFPQFXZVHFB-PVYNADRNSA-N
InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1

HIDE SMILES / InChI
Molecular Formula C27H42N2O5S
Molecular Weight 506.698
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/ixabepilone.html | http://www.wikidoc.org/index.php/Ixabepilone | http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500062429.pdf

Ixabepilone is an antineoplastic agent, epothilone and mitotic inhibitor that is FDA approved for the treatment of patients with metastatic or locally advanced breast cancer resistant to treatment with an anthracycline and a taxane, or whose cancer is taxane resistant and for whom further anthracycline therapy is contraindicated. Ixabepilone binds directly to beta-tubulin subunits on microtubules, leading to suppression of microtubule dynamics. Ixabepilone suppresses the dynamic instability of alpha-beta-II and alpha-beta-III microtubules. The most common adverse reactions (≥20%) are peripheral sensory neuropathy, fatigue/asthenia, myalgia/arthralgia, alopecia, nausea, vomiting, stomatitis/mucositis, diarrhea, and musculoskeletal pain. Inhibitors of CYP3A4 may increase plasma concentrations of ixabepilone.

Originator

Bristol-Myers Squibb
144
Curator's Comment: # Bristol-Myers Squibb Company

Approval Year

2007
239
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 10.6 µM [EC50]
Substrate
661
 7.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
IXEMPRA KIT

Approved Use

IXEMPRA is indicated as monotherapy or in combination with capecitabine for the treatment of patients with metastatic or locally advanced breast cancer resistant to treatment with an anthracycline and a taxane, or whose cancer is taxane resistant and for whom further anthracycline therapy is contraindicated.

Launch Date

2007
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
252 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022065s002lbl.pdf
40 mg/m² single, intravenous
dose: 40 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IXABEPILONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2143 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022065s002lbl.pdf
40 mg/m² single, intravenous
dose: 40 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IXABEPILONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
52 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022065s002lbl.pdf
40 mg/m² single, intravenous
dose: 40 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IXABEPILONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
28%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022065s002lbl.pdf
40 mg/m² single, intravenous
dose: 40 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IXABEPILONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Disc. AE: Neuropathic pain...
Other AEs: Anorexia, Stomatitis...
AEs leading to
discontinuation/dose reduction:
Neuropathic pain (grade 3, 1 patient)
Other AEs:
Anorexia (grade 3, 1 patient)
Stomatitis (grade 3, 1 patient)
Neutropenia (grade 4, 1 patient)
Fever (grade 3, 1 patient)
Dehydration (grade 3, 1 patient)
Nausea (grade 3, 1 patient)
Vomiting (grade 3, 1 patient)
Dizziness (grade 3, 1 patient)
Sensory neuropathy (grade 3, 1 patient)
Myalgia (grade 3, 1 patient)
Alopecia (grade 2, 2 patients)
Bilirubin increased (grade 2, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
10 mg/m2 1 times / day multiple, intravenous
Dose: 10 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
DLT: Neutropenia, Fatigue...
Dose limiting toxicities:
Neutropenia (grade 4, 2 patients)
Fatigue (grade 3, 2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
6 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 6 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 6 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
unhealthy, 18-80 years
Health Status: unhealthy
Age Group: 18-80 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
Other AEs: Fatigue, Anorexia...
Other AEs:
Fatigue (grade 3, 4 patients)
Anorexia (grade 3, 1 patient)
Mucositis (grade 3, 1 patient)
Neutropenia (grade 3, 13 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
8 mg/m2 1 times / day multiple, intravenous
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
unhealthy, 18-80 years
Health Status: unhealthy
Age Group: 18-80 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 4, 3 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
6.8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 6.8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 6.8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
unhealthy, 54 years (range: 22–75 years)
Health Status: unhealthy
Age Group: 54 years (range: 22–75 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
DLT: Low platelets, Arthralgia...
Dose limiting toxicities:
Low platelets (grade 3, 1 patient)
Arthralgia (grade 3, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
7 mg/m2 1 times / day multiple, intravenous
Dose: 7 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 7 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
unhealthy, 54 years (range: 22–75 years)
Health Status: unhealthy
Age Group: 54 years (range: 22–75 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
DLT: Febrile neutropenia...
Dose limiting toxicities:
Febrile neutropenia (grade 3, 2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
50 mg 3 times / day multiple, oral
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
unhealthy, 56 years (range: 27–60 years)
Health Status: unhealthy
Age Group: 56 years (range: 27–60 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
DLT: Neutropenic sepsis...
Dose limiting toxicities:
Neutropenic sepsis (grade 4, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
40 mg 3 times / day multiple, oral
MTD
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
unhealthy, 69 years (range: 39–75 years)
Health Status: unhealthy
Age Group: 69 years (range: 39–75 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
DLT: Febrile neutropenia...
Other AEs: Mucosal inflammation...
Dose limiting toxicities:
Febrile neutropenia (grade 4, 1 patient)
Other AEs:
Mucosal inflammation (grade 3-4, 2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
100 mg/m2 single, intravenous
Overdose
Dose: 100 mg/m2
Route: intravenous
Route: single
Dose: 100 mg/m2
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
Other AEs: Myalgia, Fatigue...
Other AEs:
Myalgia (grade 1, 1 patient)
Fatigue (grade 1, 1 patient)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
40 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 40 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 40 mg/m2, 1 times / 3 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
Other AEs: Neutropenia...
Other AEs:
Neutropenia (grade 5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Bilirubin increased grade 2, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Alopecia grade 2, 2 patients
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Anorexia grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Dehydration grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Dizziness grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Fever grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Myalgia grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Nausea grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Sensory neuropathy grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Stomatitis grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Vomiting grade 3, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Neuropathic pain grade 3, 1 patient
Disc. AE
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Neutropenia grade 4, 1 patient
8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Fatigue grade 3, 2 patients
DLT
10 mg/m2 1 times / day multiple, intravenous
Dose: 10 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Neutropenia grade 4, 2 patients
DLT
10 mg/m2 1 times / day multiple, intravenous
Dose: 10 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 10 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
unhealthy, 10 years (range: 2 - 18 years)
Health Status: unhealthy
Age Group: 10 years (range: 2 - 18 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/19075272
Anorexia grade 3, 1 patient
6 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 6 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 6 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
unhealthy, 18-80 years
Health Status: unhealthy
Age Group: 18-80 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
Mucositis grade 3, 1 patient
6 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 6 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 6 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
unhealthy, 18-80 years
Health Status: unhealthy
Age Group: 18-80 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
Neutropenia grade 3, 13 patients
6 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 6 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 6 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
unhealthy, 18-80 years
Health Status: unhealthy
Age Group: 18-80 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
Fatigue grade 3, 4 patients
6 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 6 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 6 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
unhealthy, 18-80 years
Health Status: unhealthy
Age Group: 18-80 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
Neutropenia grade 4, 3 patients
DLT
8 mg/m2 1 times / day multiple, intravenous
Dose: 8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
unhealthy, 18-80 years
Health Status: unhealthy
Age Group: 18-80 years
Sources:
https://pubmed.ncbi.nlm.nih.gov/12721265
Arthralgia grade 3, 1 patient
DLT
6.8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 6.8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 6.8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
unhealthy, 54 years (range: 22–75 years)
Health Status: unhealthy
Age Group: 54 years (range: 22–75 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
Low platelets grade 3, 1 patient
DLT
6.8 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 6.8 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 6.8 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
unhealthy, 54 years (range: 22–75 years)
Health Status: unhealthy
Age Group: 54 years (range: 22–75 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
Febrile neutropenia grade 3, 2 patients
DLT
7 mg/m2 1 times / day multiple, intravenous
Dose: 7 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 7 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
unhealthy, 54 years (range: 22–75 years)
Health Status: unhealthy
Age Group: 54 years (range: 22–75 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/20449631
Neutropenic sepsis grade 4, 1 patient
DLT
50 mg 3 times / day multiple, oral
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
unhealthy, 56 years (range: 27–60 years)
Health Status: unhealthy
Age Group: 56 years (range: 27–60 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
Mucosal inflammation grade 3-4, 2 patients
40 mg 3 times / day multiple, oral
MTD
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
unhealthy, 69 years (range: 39–75 years)
Health Status: unhealthy
Age Group: 69 years (range: 39–75 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
Febrile neutropenia grade 4, 1 patient
DLT
40 mg 3 times / day multiple, oral
MTD
Dose: 40 mg, 3 times / day
Route: oral
Route: multiple
Dose: 40 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
unhealthy, 69 years (range: 39–75 years)
Health Status: unhealthy
Age Group: 69 years (range: 39–75 years)
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/22331549
Fatigue grade 1, 1 patient
100 mg/m2 single, intravenous
Overdose
Dose: 100 mg/m2
Route: intravenous
Route: single
Dose: 100 mg/m2
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
Myalgia grade 1, 1 patient
100 mg/m2 single, intravenous
Overdose
Dose: 100 mg/m2
Route: intravenous
Route: single
Dose: 100 mg/m2
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
Neutropenia grade 5
40 mg/m2 1 times / 3 weeks multiple, intravenous
Recommended
Dose: 40 mg/m2, 1 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 40 mg/m2, 1 times / 3 weeks
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/022065lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
1087

substrate
1946
inducer
440

inhibitor
2438

substrate
1193
inhibitor
2507

substrate
1388
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2A6
879

CYP2B6
926

CYP2C19
2057

CYP2C8
1057

CYP2E1
1060

CYP3A4/5
296

P-gp
1741
BCRP
697

CYP1A2
1197

CYP2B6
776

CYP2C19
1119

CYP2C8
810

CYP2E1
729

CYP3A4/5
91

CYP3A5
446

P-gp
2052
CYP1A2
832

CYP2B6
669
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1932
 inconclusive
CYP1A2
2333
 no [IC50 >30 uM]
unlikely
Comment: ixabepilone is not likely to be an inhibitor of CYP450 enzymes or cause drug-drug interactions via CYP450 inhibition with coadministered drugs that are metabolized by CYP450 enzymes in-vivo
Page: 31.0
CYP2A6
911
 no [IC50 >30 uM]
unlikely
Comment: ixabepilone is not likely to be an inhibitor of CYP450 enzymes or cause drug-drug interactions via CYP450 inhibition with coadministered drugs that are metabolized by CYP450 enzymes in-vivo
Page: 31.0
CYP2B6
1160
 no [IC50 >30 uM]
unlikely
Comment: ixabepilone is not likely to be an inhibitor of CYP450 enzymes or cause drug-drug interactions via CYP450 inhibition with coadministered drugs that are metabolized by CYP450 enzymes in-vivo
Page: 31.0
CYP2C19
2141
 no [IC50 >30 uM]
unlikely
Comment: ixabepilone is not likely to be an inhibitor of CYP450 enzymes or cause drug-drug interactions via CYP450 inhibition with coadministered drugs that are metabolized by CYP450 enzymes in-vivo
Page: 31.0
CYP2C8
1117
 no [IC50 >30 uM]
unlikely
Comment: ixabepilone is not likely to be an inhibitor of CYP450 enzymes or cause drug-drug interactions via CYP450 inhibition with coadministered drugs that are metabolized by CYP450 enzymes in-vivo
Page: 31.0
CYP2C9
2497
 no [IC50 >30 uM]
unlikely
Comment: ixabepilone is not likely to be an inhibitor of CYP450 enzymes or cause drug-drug interactions via CYP450 inhibition with coadministered drugs that are metabolized by CYP450 enzymes in-vivo
Page: 31.0
CYP2D6
2546
 no [IC50 >30 uM]
unlikely
Comment: ixabepilone is not likely to be an inhibitor of CYP450 enzymes or cause drug-drug interactions via CYP450 inhibition with coadministered drugs that are metabolized by CYP450 enzymes in-vivo
Page: 31.0
CYP2E1
1146
 no [IC50 >30 uM]
unlikely
Comment: ixabepilone is not likely to be an inhibitor of CYP450 enzymes or cause drug-drug interactions via CYP450 inhibition with coadministered drugs that are metabolized by CYP450 enzymes in-vivo
Page: 31.0
CYP1A2
2333
 no
CYP2B6
1160
 no
CYP2C9
2497
 no
CYP3A4
2633
 no
CYP3A4/5
357
 yes [IC50 15 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 inconclusive
CYP3A4
1946
 major
yes (co-administration study)
Comment: coadministration with ketoconazole increased AUC by 1.8-fold but no difference in Cmax values; CYP3A4 inhibitors should be used with caution in patients taking ixabepilone.
Page: 30, 34
BCRP
697
 no
CYP1A2
1197
 no
CYP2B6
776
 no
CYP2C8
810
 no
CYP2C9
1193
 no
CYP2E1
729
 no
CYP2C19
1119
 yes
CYP2D6
1388
 yes
CYP3A4/5
91
 yes
CYP3A5
446
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:63605
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63605
ChemicalBook
CB61011739
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB61011739
MolPort
MolPort-027-720-838
https://www.molport.com/shop/molecule-link/MolPort-027-720-838
ZINC
ZINC000003993846
http://zinc15.docking.org/substances/ZINC000003993846
PubMed

PubMed

TitleDatePubMed
[Efficacy and safety of ixabepilone (BMS-247550), a novel epothilone B analogue].
2008-02
Patents

Patents

JP2006519264A
58
JP2011527579A
29
JP2011529067A
37
JP4658037B2
37

Sample Use Guides

In Vivo Use Guide
40 mg/m2 infused over 3 hours every 3 weeks
Route of Administration: Intravenous
In Vitro Use Guide
Hepatocellular carcinoma cell lines were sensitive to ixabepilone, with the IC50 range 2.5–44.1 nmol/l.
Substance Class Chemical
Created
by admin
on Wed Apr 02 07:43:28 GMT 2025
Edited
by admin
on Wed Apr 02 07:43:28 GMT 2025
Record UNII
K27005NP0A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IXABEPILONE
DASH   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
IXEMPRA
Preferred Name English
IXABEPILONE [MART.]
Common Name English
IXABEPILONE [MI]
Common Name English
1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-((1E)-1-METHYL-2-(2-METHYLTHIAZOL-4-YL)ETHENYL)-17-OXA-4-AZABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE
Common Name English
ixabepilone [INN]
Common Name English
AZAEPOTHILONE B
Common Name English
NSC-747973
Code English
BMS-247550
Code English
IXABEPILONE [USP-RS]
Common Name English
(1R,5S,6S,7R,10S,14S,16S)-6,10-DIHYDROXY-1,5,7,9,9-PENTAMETHYL-14-((E)-1-(2-METHYL-1,3-THIAZOL-4-YL)PROP-1-EN-2-YL)-17-OXA-13-AZABICYCLO(14.1.0)HEPTADECANE-8,12-DIONE
Systematic Name English
IXABEPILONE [USAN]
Common Name English
IXABEPILONE [ORANGE BOOK]
Common Name English
IXABEPILONE [HSDB]
Common Name English
IXABEPILONE [VANDF]
Common Name English
BMS-247550-01
Code English
Ixabepilone [WHO-DD]
Common Name English
IXEMPRA KIT
Brand Name English
IXABEPILONE [JAN]
Common Name English
IXABEPILONE [USP MONOGRAPH]
Common Name English
BMS 247550-01
Code English
17-OXA-4-AZABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE, 7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-((1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL)-, (1S,3S,7S,10R,11S,12S,16R)-
Common Name English
Classification Tree Code System Code
LIVERTOX NBK547985
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
NCI_THESAURUS C2584
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
NDF-RT N0000175085
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
WHO-VATC QL01DC04
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
NDF-RT N0000175592
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
WHO-ATC L01DC04
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
Code System Code Type Description
NSC
747973
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
RXCUI
337523
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB04845
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
DAILYMED
K27005NP0A
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
EVMPD
SUB33513
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
FDA UNII
K27005NP0A
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
EPA CompTox
DTXSID70870252
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
USAN
OO-38
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
SMS_ID
100000127487
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
PUBCHEM
6445540
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
CAS
219989-84-1
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
IUPHAR
6824
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201752
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
CHEBI
63605
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
DRUG CENTRAL
1517
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
RS_ITEM_NUM
1354400
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
MESH
C430592
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
MERCK INDEX
m6567
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY Merck Index
HSDB
7738
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
NCI_THESAURUS
C37452
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
WIKIPEDIA
IXABEPILONE
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
INN
8390
Created by admin on Wed Apr 02 07:43:28 GMT 2025 , Edited by admin on Wed Apr 02 07:43:28 GMT 2025
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
The percentages ixabepilone bound to proteins at concentrations of 50, 500 and 5000 ng/mL were 76.6%, 72.0% and 67.1%, respectively. The protein binding of ixabepilone was not concentration dependent from 50 ng/mL to 5000 ng/mL.
BINDING
Structure of IXABEPILONE
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
Structure of PATUPILONE
PARENT -> DERIVATIVE
Structure of IXABEPILONE
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of BMS-249798
METABOLITE -> PARENT
PLASMA
Structure of 11-HYDROXY IXABEPILONE
METABOLITE -> PARENT
FECAL; PLASMA; URINE
Structure of BMS-249798
METABOLITE -> PARENT
FECAL
Structure of IXABEPILONE DIOL
METABOLITE -> PARENT
FECAL; PLASMA; URINE
Structure of BMS-249798
METABOLITE -> PARENT
URINE
Related Record Type Details
Structure of IXABEPILONE DIOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
DESMETHYL IXABEPILONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (Z)-IXABEPILONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of BMS-249798
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of IXABEPILONE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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