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QuickView for Ixabepilone (compound)

Summary
General Info

PubChem

PubChem Compound 154225

PubChem Compound 154225

Name:	ixabepilone
PubChem Compound ID:	154225
Molecular formula:	C₁₇H₁₃N₃O
Molecular weight:	275.305 g/mol
Synonyms:	219959-87-2; N-Hydroxy-4-(9H-pyrido(3,4-b)indol-9-yl)benzenamine; Benzenamine, N-hydroxy-4-(9H-pyrido(3,4-b)indol-9-yl)-

DrugBank

Identification

Name:	ixabepilone
Name (isomeric):	DB04845
Drug Type:	small molecule
Synonyms:	BMS-247550; Azaepothilone B; Aza-epothilone B
Brand:	Ixempra
Category:	Antineoplastic Agents
CAS number:	219989-84-1

Pharmacology

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).
Mechanism of Action:	Binding of Ixabepilone to beta-tubulins (e.g. beta-III tubulin) stabilizes microtubules. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing. Like taxol, Ixabepilone binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microt... show more » Binding of Ixabepilone to beta-tubulins (e.g. beta-III tubulin) stabilizes microtubules. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing. Like taxol, Ixabepilone binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microtubules. show less «
Protein binding:	67-77%
Route of elimination:	Mostly fecal and some renal.
Half Life:	52 hours

Interactions

Drug interaction:

Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of ixabepilone by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of ixabepilone if voriconazole is initiated, discontinued or dose changed.
Conivaptan	CYP3A4 Inhibitors (Strong) may increase the serum concentration of Ixabepilone. The dose of ixabepilone must be reduced when used with strong inhibitors of CYP3A.1 In one published abstract, ixabepilone 20mg/m2 was the maximum tolerated dose in patients who were also receiving the CYP3A-inhibitor ketoconazole (400mg).
Telithromycin	Telithromycin may reduce clearance of Ixabepilone. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Ixabepilone if Telithromycin is initiated, discontinued or dose changed.

Targets

Tubulin beta-3 chain

Enzymes

Cytochrome P450 3A4