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Ixabepilone

drug
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Also known as Azaepothilone bBMS-247550IxabepilonaIxempraIxempra kitNSC-747973IxabepiloneXempra

Summary

Ixabepilone (CHEMBL1201752) is an approved small-molecule antineoplastic agent (ATC L01DC04) targeting TUBB; indicated across 42 conditions including breast carcinoma and neoplasm.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: L01DC04
  • Targets: 1 (TUBB)
  • Indications: 42 conditions
  • Clinical trials: 109
  • Chemistry: 506.7 Da · C27H42N2O5S

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1201752
NameIxabepilone
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID6445540
ChEBICHEBI:63605
ATCL01DC04
Molecular formulaC27H42N2O5S
Molecular weight506.7
InChIKeyFABUFPQFXZVHFB-PVYNADRNSA-N

SMILES: C[C@H]1CCC[C@@]2([C@@H](O2)C[C@H](NC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)C)/C)C

IUPAC name: (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione

ChEBI definition: A macrocycle that is a lactam analogue of epothilone B. Binds directly to beta-tubulin subunits on microtubules, leading to suppression of microtubule dynamics.

Pharmacological roles (ChEBI): antineoplastic agent, microtubule-destabilising agent.

Also known as: Azaepothilone b, BMS-247550, Ixabepilona, Ixabepilone, Ixempra, Ixempra kit, NSC-747973, ixabepilone, IXABEPILONE, Ixabepilone; Xempra

Patent coverage: 6,727 distinct patent families (25,437 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
TUBBtubulin beta class IInhibitionP07437

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Apoptosis regulator Bcl-2.

Bioactivity

ChEMBL activities: 1 potent at pChembl ≥ 5 of 1 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
BCL26.47Kd337nMCHEMBL_ACT_22969871

Target pathways

Aggregated over 1 target gene(s): TUBB.

Top Reactome pathways

24 total, by targets touching each:

PathwayTargetsGenes
Cell Cycle1TUBB
Disease1TUBB
Innate Immune System1TUBB
Immune System1TUBB
Organelle biogenesis and maintenance1TUBB
Regulation of PLK1 Activity at G2/M Transition1TUBB
Loss of Nlp from mitotic centrosomes1TUBB
Recruitment of mitotic centrosome proteins and complexes1TUBB
Loss of proteins required for interphase microtubule organization from the centrosome1TUBB
Centrosome maturation1TUBB
Recruitment of NuMA to mitotic centrosomes1TUBB
Mitotic G2-G2/M phases1TUBB
Cilium Assembly1TUBB
Anchoring of the basal body to the plasma membrane1TUBB
Infectious disease1TUBB
Neutrophil degranulation1TUBB
Mitotic Prometaphase1TUBB
M Phase1TUBB
G2/M Transition1TUBB
Cell Cycle, Mitotic1TUBB
AURKA Activation by TPX21TUBB
Potential therapeutics for SARS1TUBB
SARS-CoV Infections1TUBB
Viral Infection Pathways1TUBB

Dominant GO biological processes

GO termTargets
microtubule cytoskeleton organization1
mitotic cell cycle1
microtubule-based process1
cytoskeleton-dependent intracellular transport1
natural killer cell mediated cytotoxicity1
regulation of synapse organization1
spindle assembly1
cell division1
odontoblast differentiation1
cytoskeleton organization1

Indications & clinical

Indications

42 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
breast carcinoma4MONDO:0004989EFO:0000305
neoplasm4MONDO:0005070EFO:0000616
breast neoplasm4MONDO:0021100EFO:0003869
endometrium neoplasm3MONDO:0021251MONDO:0011962
gastric neoplasm2MONDO:0021085EFO:0003897
melanoma2MONDO:0005105EFO:0000756
prostate adenocarcinoma2MONDO:0005082EFO:0000673
clear cell renal carcinoma2MONDO:0005005EFO:0000349
Burkitt lymphoma2MONDO:0007243EFO:0000309
diffuse large B-cell lymphoma2MONDO:0018905EFO:0000403
leukemia2MONDO:0005059EFO:0000565
lymphoma2MONDO:0005062EFO:0000574
renal cell carcinoma2MONDO:0005086EFO:0000681
exocrine pancreatic carcinoma2MONDO:0005192EFO:0002618
anaplastic large cell lymphoma2MONDO:0020325EFO:0003032
non-small cell lung carcinoma2MONDO:0005233EFO:0003060
male breast carcinoma2MONDO:0005628EFO:0006861
verrucous carcinoma2MONDO:0006006EFO:0007535
mantle cell lymphoma2MONDO:0018876EFO:1001469
hypopharyngeal carcinoma2MONDO:0005216EFO:0002938
uterine carcinosarcoma2MONDO:0006485EFO:1000613
soft tissue sarcoma2MONDO:0018078EFO:1001968
peritoneal neoplasm2MONDO:0006901MONDO:0002087
ovarian cancer2MONDO:0008170MONDO:0008170
lung neoplasm2MONDO:0021117MONDO:0008903
follicular lymphoma2MONDO:0018906MONDO:0018906
oropharynx cancer2MONDO:0004608MONDO:0044926
laryngeal squamous cell carcinoma2MONDO:0005595EFO:0006352
cholangiocarcinoma2MONDO:0019087EFO:0005221
gallbladder neoplasm2MONDO:0021253MONDO:0005411
bile duct carcinoma2MONDO:0005496EFO:0005540
tongue cancer2MONDO:0004631MONDO:0004631
colorectal neoplasm2MONDO:0005335MONDO:0005575
anaplastic astrocytoma1MONDO:0016684EFO:0002499
head and neck cancer1MONDO:0005627EFO:0006859
gliosarcoma1MONDO:0016681EFO:1001465

6 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 109.

Phase distribution

PhaseTrials
PHASE258
PHASE130
PHASE1/PHASE211
PHASE38
Not specified2

Top trials by phase / activity

NCTPhaseStatusTitle
NCT00080301PHASE3COMPLETEDNovel Epothilone Plus Capecitabine Versus Capecitabine Alone in Patients With Advanced Breast Cancer
NCT00082433PHASE3COMPLETEDEpothilone (Ixabepilone) Plus Capecitabine Versus Capecitabine Alone in Patients With Advanced Breast Cancer
NCT00630032PHASE3COMPLETEDSafety and Efficacy Comparison of Docetaxel and Ixabepilone in Non Metastatic Poor Prognosis Breast Cancer
NCT00785291PHASE3COMPLETEDPaclitaxel, Nab-paclitaxel, or Ixabepilone With or Without Bevacizumab in Treating Patients With Stage IIIC or Stage IV Breast Cancer
NCT00789581PHASE3COMPLETEDA Randomized Trial of Ixempra Versus Taxol in Adjuvant Therapy of Triple Negative Breast Cancer
NCT00883116PHASE3TERMINATEDA Study of Ixabepilone as Second-line Therapy for Locally Advanced, Recurrent, or Metastatic Endometrial Cancer
NCT00998738PHASE3TERMINATEDCalcium and Magnesium in Preventing Peripheral Neuropathy Caused by Ixabepilone in Patients With Breast Cancer
NCT02915744PHASE3COMPLETEDA Study of Etirinotecan Pegol (NKTR-102) Versus Treatment of Physician’s Choice (TPC) in Patients With Metastatic Breast Cancer Who Have Stable Brain Metastases and Have Been Previously Treated With an Anthracycline, a Taxane, and Capecitabine
NCT00877500PHASE2ACTIVE_NOT_RECRUITINGIxabepilone in Treating Participants With Significant Residual Disease of HER2/Neu Negative Invasive Breast Cancer After Systemic Therapy
NCT00977574PHASE2ACTIVE_NOT_RECRUITINGPaclitaxel, Carboplatin, and Bevacizumab or Paclitaxel, Carboplatin, and Temsirolimus or Ixabepilone, Carboplatin, and Bevacizumab in Treating Patients With Stage III, Stage IV, or Recurrent Endometrial Cancer
NCT00016393PHASE2COMPLETEDBMS-247550 in Treating Patients With Prostate Cancer That Has Not Responded to Hormone Therapy
NCT00016965PHASE2COMPLETEDBMS-247550 in Treating Patients With Advanced Pancreatic Cancer
NCT00017043PHASE2COMPLETEDBMS-247550 in Treating Patients With Metastatic Stomach Cancer Previously Treated With Chemotherapy
NCT00017056PHASE2COMPLETEDBMS-247550 in Treating Patients With Recurrent Metastatic Stomach Cancer That Has Been Previously Treated With Chemotherapy
NCT00020904PHASE2COMPLETEDBMS-247550 in Treating Women With Metastatic Breast Cancer
NCT00021099PHASE2COMPLETEDIxabepilone in Treating Patients With Advanced Urinary Tract Cancer
NCT00022477PHASE2COMPLETEDBMS-247550 in Treating Patients With Recurrent or Metastatic Colorectal Cancer
NCT00022542PHASE2TERMINATEDBMS-247550 in Treating Patients With Advanced Soft Tissue Sarcoma
NCT00023946PHASE2TERMINATEDBMS-247550 in Treating Patients With Liver or Gallbladder Cancer
NCT00025155PHASE2COMPLETEDIxabepilone in Treating Patients With Ovarian Epithelial or Primary Peritoneal Cancer That Has Not Responded to Previous Chemotherapy
NCT00025194PHASE1/PHASE2COMPLETEDIxabepilone With or Without Estramustine in Treating Patients With Progressive Prostate Cancer
NCT00030706PHASE2COMPLETEDIxabepilone in Treating Patients With Relapsed and/or Refractory Stage III or Stage IV Ovarian Epithelial or Primary Peritoneal Cancer
NCT00030992PHASE2COMPLETEDBMS 247550 to Treat Kidney Cancer
NCT00033306PHASE2TERMINATEDBMS-247550 in Treating Patients With Metastatic Colorectal Cancer
NCT00033618PHASE2COMPLETEDIxabepilone in Treating Patients With Metastatic or Recurrent Squamous Cell Cancer of the Head and Neck
NCT00036764PHASE2COMPLETEDBMS-247550 in Treating Patients With Stage IV Melanoma
NCT00045097PHASE2COMPLETEDIxabepilone in Treating Patients With Locally Advanced or Metastatic Breast Cancer
NCT00045708PHASE1/PHASE2COMPLETEDA Phase I/II Trial of BMS-247550 for Treatment of Patients With Recurrent High-Grade Gliomas
NCT00052572PHASE2COMPLETEDIxabepilone in Treating Patients With Relapsed or Refractory Lymphoproliferative Disorders
NCT00057850PHASE1/PHASE2COMPLETEDBMS-247550 Plus Cisplatin in Treating Patients With Metastatic or Recurrent Head and Neck Cancer
NCT00058019PHASE2COMPLETEDIxabepilone in Treating Patients With Relapsed or Refractory Aggressive Non-Hodgkin’s Lymphoma
NCT00058084PHASE2COMPLETEDIxabepilone Compared With Mitoxantrone and Prednisone in Treating Patients With Refractory Metastatic Prostate Cancer
NCT00070096PHASE2COMPLETEDIxabepilone in Treating Patients With Advanced Cisplatin-Refractory Germ Cell Tumors
NCT00077376PHASE2COMPLETEDTrastuzumab, Ixabepilone, and Carboplatin in Treating Patients With HER2/Neu-Positive Metastatic Breast Cancer
NCT00079326PHASE2TERMINATEDTrastuzumab and Ixabepilone in Treating Women With HER2-Positive Metastatic Breast Cancer
NCT00080262PHASE2COMPLETEDNovel Epothilone (BMS-247550) in Patients With Metastatic Breast Cancer (MBC)
NCT00087139PHASE2COMPLETEDIxabepilone in Treating Patients With Metastatic Prostate Cancer
NCT00095979PHASE2COMPLETEDIxabepilone in Treating Patients With Recurrent or Persistent Endometrial Cancer
NCT00182702PHASE2COMPLETEDIxabepilone in Treating Patients With Metastatic, Recurrent, or Unresectable Kidney Cancer
NCT00182767PHASE1/PHASE2COMPLETEDIxabepilone and Liposomal Doxorubicin in Advanced Ovarian Cancer

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

18 molecules share ≥1 primary target. Top 18 by shared-target count:

MoleculeSourceStatusShared targets
PODOFILOXChEMBL + PubChemPhase 4 (approved)TUBB
VINBLASTINEChEMBL + PubChemPhase 4 (approved)TUBB
COLCHICINEChEMBLPhase 4 (approved)TUBB
DOCETAXELChEMBLPhase 4 (approved)TUBB
LEVOFLOXACINChEMBLPhase 4 (approved)TUBB
NOSCAPINEChEMBLPhase 4 (approved)TUBB
PACLITAXELChEMBLPhase 4 (approved)TUBB
TIRBANIBULINChEMBLPhase 4 (approved)TUBB
VINCRISTINEChEMBLPhase 4 (approved)TUBB
VINORELBINEChEMBLPhase 4 (approved)TUBB
PATUPILONEChEMBLPhase 3TUBB
ABT-751ChEMBLPhase 2TUBB
DOLASTATIN-10ChEMBLPhase 2TUBB
INDIBULINChEMBLPhase 2TUBB
MAYTANSINEChEMBLPhase 2TUBB
MOLIBRESIBChEMBLPhase 2TUBB
NOCODAZOLEChEMBLPhase 2TUBB
PARBENDAZOLEChEMBLPhase 2TUBB

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot