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
Defined Stereocenters 7 / 7
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.6 µM [EC50]
7.3 µM [IC50]
Conditions
PubMed

PubMed

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

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 Mon Oct 21 21:00:42 UTC 2019
Edited
by admin
on Mon Oct 21 21:00:42 UTC 2019
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
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
BMS-247550
Code 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
IXEMPRA KIT
Brand Name English
IXABEPILONE [JAN]
Common Name English
IXEMPRA
Brand 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
IXABEPILONE [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 528
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
NCI_THESAURUS C2584
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
NDF-RT N0000175085
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
WHO-VATC QL01DC04
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
NDF-RT N0000175592
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
WHO-ATC L01DC04
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
Code System Code Type Description
RXCUI
337523
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB04845
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
EVMPD
SUB33513
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
PUBCHEM
6445540
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
CAS
219989-84-1
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
IUPHAR
6824
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
ChEMBL
CHEMBL1201752
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
MESH
C430592
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
MERCK INDEX
M6567
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY Merck Index
HSDB
219989-84-1
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
NCI_THESAURUS
C37452
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
WIKIPEDIA
IXABEPILONE
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
INN
8390
Created by admin on Mon Oct 21 21:00:43 UTC 2019 , Edited by admin on Mon Oct 21 21:00:43 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
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
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC