ixabepilone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1517 219989-84-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ixabepilone
  • Azaepothilone B
  • ixempra
  • BMS-247550
Ixabepilone is a semi-synthetic analog of epothilone B. Ixabepilone binds directly to beta-tubulin subunits on microtubules, leading to suppression of microtubule dynamics. Ixabepilone suppresses the dynamic instability of alphaBeta-II and alphaBeta-III microtubules. Ixabepilone possesses low in vitro susceptibility to multiple tumor resistance mechanisms including efflux transporters, such as MRP-1 and P-glycoprotein (P-gp). Ixabepilone blocks cells in the mitotic phase of the cell division cycle, leading to cell death.
  • Molecular weight: 506.70
  • Formula: C27H42N2O5S
  • CLOGP: 3.52
  • LIPINSKI: 1
  • HAC: 7
  • HDO: 3
  • TPSA: 112.05
  • ALOGS: -5.16
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 5.60 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.97 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 11 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.20 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 17 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 16, 2007 FDA BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Pseudocirrhosis 181.92 36.57 30 1728 658 46683646
Neutrophil count decreased 126.78 36.57 51 1707 43375 46640929
Portal hypertension 90.96 36.57 22 1736 3461 46680843
White blood cell count decreased 80.87 36.57 51 1707 112180 46572124
Anaemia 61.99 36.57 61 1697 255718 46428586
Neutropenia 54.19 36.57 44 1714 143160 46541144
Febrile neutropenia 46.52 36.57 34 1724 94593 46589711
Malignant neoplasm progression 42.90 36.57 28 1730 64898 46619406
Platelet count decreased 42.63 36.57 33 1725 99991 46584313
Disease progression 38.63 36.57 30 1728 91270 46593034

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC L01DC04 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES
Other cytotoxic antibiotics
FDA PE N0000175085 Microtubule Inhibition
FDA EPC N0000175592 Microtubule Inhibitor
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:61951 microtubule destabilising role

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Carcinoma of breast indication 254838004 DOID:3459
Metastatic Breast Carcinoma indication
Hyperbilirubinemia contraindication 14783006 DOID:2741
Conduction disorder of the heart contraindication 44808001
Heart disease contraindication 56265001 DOID:114
Hepatic failure contraindication 59927004
Acute infectious disease contraindication 63171007
Diabetes mellitus contraindication 73211009 DOID:9351
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Peripheral nerve disease contraindication 302226006
Neutropenic disorder contraindication 303011007 DOID:1227
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.56 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Tubulin beta Tumour-associated antigen INHIBITOR SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE

External reference:

IDSource
4026737 VUID
N0000179767 NUI
D04645 KEGG_DRUG
4026737 VANDF
C1135132 UMLSCUI
CHEBI:63605 CHEBI
GZX PDB_CHEM_ID
CHEMBL1201752 ChEMBL_ID
DB04845 DRUGBANK_ID
6445540 PUBCHEM_CID
C430592 MESH_SUPPLEMENTAL_RECORD_UI
6824 IUPHAR_LIGAND_ID
8390 INN_ID
K27005NP0A UNII
337523 RXNORM
121505 MMSL
24628 MMSL
d07051 MMSL
012371 NDDF
428282007 SNOMEDCT_US
429022006 SNOMEDCT_US

Pharmaceutical products:

None