ixabepilone ๐Ÿถ Veterinary Use | 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: 3.67
  • 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 ยตM/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 189.37 37.69 30 1784 677 63486531
Neutrophil count decreased 127.47 37.69 51 1763 56355 63430853
Portal hypertension 94.98 37.69 22 1792 3797 63483411
White blood cell count decreased 83.74 37.69 51 1763 139053 63348155
Anaemia 73.28 37.69 63 1751 293367 63193841
Neutropenia 66.08 37.69 48 1766 174957 63312251
Febrile neutropenia 48.09 37.69 34 1780 118415 63368793
Platelet count decreased 46.37 37.69 33 1781 116089 63371119
Malignant neoplasm progression 43.95 37.69 28 1786 82093 63405115
Dehydration 42.64 37.69 37 1777 173317 63313891
Disease progression 42.48 37.69 32 1782 122726 63364482

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

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 188.63 36.74 28 1420 652 79742288
Neutrophil count decreased 124.83 36.74 51 1397 93908 79649032
White blood cell count decreased 99.34 36.74 54 1394 188234 79554706
Portal hypertension 86.21 36.74 21 1427 7087 79735853
Anaemia 65.27 36.74 58 1390 444957 79297983
Neutropenia 49.14 36.74 41 1407 287669 79455271
Platelet count decreased 44.56 36.74 33 1415 194631 79548309
Febrile neutropenia 39.55 36.74 33 1415 230966 79511974
Malignant neoplasm progression 37.87 36.74 26 1422 135964 79606976

FDA Adverse Event Reporting System (Pediatric)

None

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 antineoplastic agents
CHEBI has role CHEBI:61951 microtubule destabilizing role

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
15MG/VIAL IXEMPRA KIT R-PHARM US LLC N022065 Oct. 16, 2007 RX INJECTABLE INTRAVENOUS 7312237 Aug. 21, 2024 USE OF IXABEPILONE IN COMBINATION WITH CAPECITABINE IN TREATMENT OF METASTASIS BREAST CANCER
45MG/VIAL IXEMPRA KIT R-PHARM US LLC N022065 Oct. 16, 2007 RX INJECTABLE INTRAVENOUS 7312237 Aug. 21, 2024 USE OF IXABEPILONE IN COMBINATION WITH CAPECITABINE IN TREATMENT OF METASTASIS BREAST CANCER

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
Apoptosis regulator Bcl-2 Cytosolic other Kd 6.47 CHEMBL

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
C430592 MESH_SUPPLEMENTAL_RECORD_UI
6824 IUPHAR_LIGAND_ID
8390 INN_ID
K27005NP0A UNII
6445540 PUBCHEM_CID
337523 RXNORM
121505 MMSL
24628 MMSL
d07051 MMSL
012371 NDDF
428282007 SNOMEDCT_US
429022006 SNOMEDCT_US

Pharmaceutical products:

None