Ixabepilone
(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
Molecular Identity
Ixabepilone
(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
PubChem CID: 6445540
Ixabepilone is a macrocycle that is a lactam analogue of epothilone B. Binds directly to beta-tubulin subunits on microtubules, leading to suppression of microtubule dynamics. It has a role as an antineoplastic agent and a microtubule-destabilising agent. It is a lactam, an epoxide, a member of 1,3-thiazoles, a macrocycle and a beta-hydroxy ketone.
2D Structure
Properties
C27H42N2O5S
Molecular Formula
506.70
Molecular Weight
g/mol
506.2814
Exact Mass
Da
3.6
XLogP
Drug-like (Lipinski: < 5)
140
TPSA
May have limited oral absorption
3
H-Bond Donors
7
H-Bond Acceptors
817
Complexity
SMILES
Canonical SMILES
SMILES: CC1CCCC2(C(O2)CC(NC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C)CIsomeric SMILES
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)CSynonyms(20)
Ixabepilone219989-84-1Azaepothilone BIxempraBMS-247550Aza-epothilone BIxempra kitBMS 247550-01ixabepilonaNSC-747973BMS 247550-1BMS-247550-01CHEBI:63605DTXSID70870252K27005NP0A
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Ixabepilone
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