ixabepilone

Also known as BMS-247550-01, Ixempra, Aza-epothilone B, Azaepothilone B, Ixempra Kit, BMS-247550

Ixabepilone (INN; also known as azaepothilone B, codenamed BMS-247550) is a pharmaceutical drug developed by Bristol-Myers Squibb as a chemotherapeutic medication for cancer.

Chemical data

Formula: C27H42N2O5S
Molecular weight: 506.7 g/mol
IUPAC name: (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
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)C
InChIKey: FABUFPQFXZVHFB-PVYNADRNSA-N
XLogP: 3.6
Polar surface area: 140 Å²
H-bond donors: 3
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2007
Admin. routes: parenteral
Indications: breast carcinoma, neoplasm, stomach neoplasm, melanoma

via ChEMBL · EBI

Research

484 papers

Ixabepilone.2012
Ixabepilone.Clinical journal of oncology nursing · 2010
Ixabepilone-Induced Delirium.American journal of therapeutics · 2024
Ixabepilone: Overview of Effectiveness, Safety, and Tolerability in Metastatic Breast Cancer.Frontiers in oncology · 2021
A phase II study of frontline paclitaxel/carboplatin/bevacizumab, paclitaxel/carboplatin/temsirolimus, or ixabepilone/carboplatin/bevacizumab in advanced/recurrent endometrial cancer.Gynecologic oncology · 2018

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 506.281443
Has use: medication

Show 5 more facts

chemical formula: C₂₇H₄₂N₂O₅S
canonical SMILES: CC1CCCC2(C(O2)CC(NC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C)C
isomeric 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)C
World Health Organisation international non-proprietary name: ixabepilone
legal status (medicine): boxed warning

Sources (6)

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Encyclopedic overview

6 sections

Contents

History
Pharmacology
Approval
Clinical uses
References
External links

Ixabepilone (INN; also known as azaepothilone B, codenamed BMS-247550) is a pharmaceutical drug developed by Bristol-Myers Squibb as a chemotherapeutic medication for cancer.

==History== Ixabepilone is a semi-synthetic analog of epothilone B, a natural chemical compound produced by Sorangium cellulosum. The structural difference between Epothilone B and Ixabepilone consists of only a single atom oxygen-to-nitrogen subsitution that converts the ester into an amide. Epothilone B itself could not be developed as a pharmaceutical drug because of poor metabolic stability and pharmacokinetics. Ixabepilone was designed through medicinal chemistry to improve upon these properties.

Excerpted from Wikipedia’s “ixabepilone” article, available under the CC BY-SA 4.0 licence.

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