ChemSpider 2D Image | Ixabepilone | C27H42N2O5S

Ixabepilone

  • Molecular FormulaC27H42N2O5S
  • Average mass506.698 Da
  • Monoisotopic mass506.281433 Da
  • ChemSpider ID20145579
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 7 of 7 defined stereocentres


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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecan-5,9-dion [German] [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentaméthyl-3-[(1E)-1-(2-méthyl-1,3-thiazol-4-yl)-1-propén-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadécane-5,9-dione [French] [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-17-oxa-4-azabicyclo[14.1.0]heptadecan-5,9-dion [German]
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentaméthyl-3-[(E)-1-méthyl-2-(2-méthyl-1,3-thiazol-4-yl)éthényl]-17-oxa-4-azabicyclo[14.1.0]heptadécane-5,9-dione [French]
17-Oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (1S,3S,7S,10R,11S,12S,16R)- [ACD/Index Name]
219989-84-1 [RN]
8390
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

BMS 247550-01 [DBID]
BMS-247550 [DBID]
CHEBI:63605 [DBID]
BMS 247550 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      L01DC04 Wikidata Q11711607
    • Chemical Class:

      A macrocycle that is a lactam analogue of epothilone B. Binds directly to beta-tubulin subunits on microtubules, leading to suppression of microtubule dynamics. ChEBI CHEBI:63605
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-10222
      Cell Cycle/DNA Damage; MedChem Express HY-10222
      Ixabepilone (Azaepothilone B; BMS 247550) is an epothilone B analog and nontaxane microtubule-stabilizing compound with clinical activity in a range of solid tumors.; IC50 Value:; Target: Microtubule/Tubulin; in vitro: BMS-247550 (EpoB), a novel epothilone B analogue, induces cell cycle arrest at the G(2)-M phase transition and subsequent apoptotic cell death of MDA-MB-468 (468) cells. MedChem Express HY-10222
      Ixabepilone (Azaepothilone B; BMS 247550) is an epothilone B analog and nontaxane microtubule-stabilizing compound with clinical activity in a range of solid tumors.;IC50 Value:;Target: Microtubule/Tubulin;In vitro: BMS-247550 (EpoB), a novel epothilone B analogue, induces cell cycle arrest at the G(2)-M phase transition and subsequent apoptotic cell death of MDA-MB-468 (468) cells. ;In vivo: Ixabepilone, on a once every 21-day schedule, is modestly active against metastatic gastric cancer previously treated with a taxane. The days 1-5 every 21 days schedule had a more favorable safety profile but no activity. The results of this study suggest that once every 21-day ixabepilone schedule should be pursued further in untreated gastric or gastroesophageal adenocarcinoma patients. Ixabepilone has demonstrated activity in patients with chemotherapy-naive metastatic HRPC. Major toxicities were neutropenia and neuropathy. Further testing to define its activity relative to standard therap MedChem Express HY-10222
      Microtubule/Tubulin MedChem Express HY-10222

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.1±0.1 g/cm3
Boiling Point: 697.8±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.3 mmHg at 25°C
Enthalpy of Vaporization: 107.3±3.0 kJ/mol
Flash Point: 375.8±31.5 °C
Index of Refraction: 1.533
Molar Refractivity: 140.1±0.3 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 1.77
ACD/LogD (pH 5.5): 2.44
ACD/BCF (pH 5.5): 42.05
ACD/KOC (pH 5.5): 505.48
ACD/LogD (pH 7.4): 2.44
ACD/BCF (pH 7.4): 42.13
ACD/KOC (pH 7.4): 506.38
Polar Surface Area: 140 Å2
Polarizability: 55.5±0.5 10-24cm3
Surface Tension: 40.9±3.0 dyne/cm
Molar Volume: 451.6±3.0 cm3

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