(1S,3S,7R,10S,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

• ChemBase ID: 4389
• Molecular Formular: C27H42N2O5S
• Molecular Mass: 506.69778
• Monoisotopic Mass: 506.28144345
• SMILES: s1cc(nc1C)/C=C(/[C@H]1NC(=O)C[C@H](O)C(C(=O)[C@@H]([C@@H](O)[C@H](CCC[C@]2(O[C@@H]2C1)C)C)C)(C)C)\C
• Canonical SMILES: O=C1N[C@@H](C[C@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
• InChI: 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
• InChIKey: FABUFPQFXZVHFB-CFWQTKTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,7R,10S,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
• IUPAC Traditional name: (1S,3S,7R,10S,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
• Brand Name: Ixempra
• Synonyms: Azaepothilone B; BMS-247550; Aza-epothilone B; Ixabepilone

Database IDs

• CAS Number: 219989-84-1
• PubChem SID: 99443224; 160967821
• PubChem CID: 23305354

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.84502
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.392858
• LogD (pH = 7.4): 3.393564
• Log P: 3.393573
• Molar Refractivity: 136.7098 cm^3
• Polarizability: 53.83667 Å^3
• Polar Surface Area: 112.05 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.28
• LOG S: -5.16
• Solubility (Water): 3.52e-03 g/l

DETAILS

DrugBank - DB04845

• Drug Groups: approved; investigational
• Description: Ixabepilone is an epothilone B analog developed by Bristol-Myers Squibb as a cancer drug. On October 16, 2007, the U.S. Food and Drug Administration approved ixabepilone for the treatment of aggressive metastatic or locally advanced breast cancer no longer responding to currently available chemotherapies. Ixabepilone is administered through injection, and will be marketed under the trade name Ixempra. [Wikipedia] Ixabepilone is a semisynthetic analogue of epothilone B. It has a lactone–lactam modification that; minimizes susceptibility to esterase degradation.
• Indication: Investigated for use/treatment in breast cancer, head and neck cancer, melanoma, lung cancer, lymphoma (non-hodgkin's), prostate cancer, renal cell carcinoma, and cancer/tumors (unspecified).
• Half Life: 52 hours
• Protein Binding: 67-77%
• Elimination: Mostly fecal and some renal.
• External Links: Wikipedia