Azaepothilone B Uses, Dosage, Side Effects and more

Azaepothilone B is an epothilone B analog developed by Bristol-Myers Squibb as a cancer drug. It was FDA approved on October 16, 2007, for the treatment of unresponsive aggressive metastatic or locally advanced breast cancer. Azaepothilone B is administered through injection, and will be marketed under the trade name Ixempra. Azaepothilone B is a semisynthetic analogue of epothilone B. It has a lactone–lactam modification that minimizes susceptibility to esterase degradation.

Trade Name	Azaepothilone B
Availability	Prescription only
Generic	Ixabepilone
Ixabepilone Other Names	Aza-epothilone B, Azaepothilone B, Ixabepilone
Related Drugs	Arimidex, Ibrance, Femara, Xeloda, Herceptin, Lynparza
Type
Formula	C₂₇H₄₂N₂O₅S
Weight	Average: 506.7 Monoisotopic: 506.281443634
Protein binding	67-77%
Groups	Approved, Investigational
Therapeutic Class
Manufacturer
Available Country
Last Updated:	January 7, 2025 at 1:49 am

Uses

Azaepothilone B is a microtubule inhibitor administered in combination with capecitabine or alone in the treatment of metastatic or locally advanced breast cancer that has shown inadequate response to taxanes and anthracyclines.

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).

Azaepothilone B is also used to associated treatment for these conditions: Locally Advanced Breast Cancer (LABC), Metastatic Breast Cancer

How Azaepothilone B works

Binding of Azaepothilone B 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, Azaepothilone B binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microtubules.

Food Interaction

Avoid grapefruit products. Grapefruit inhibits the CYP3A4 metabolism of ixabepilone, which may increase its serum concentration.
Avoid St. John's Wort. This herb induces CYP3A metabolism and may reduce serum levels of ixabepilone.

[Moderate] GENERALLY AVOID: Grapefruit juice may increase the plasma concentrations of ixabepilone.

The proposed mechanism is inhibition of CYP450 3A4-mediated first-pass metabolism in the gut wall by certain compounds present in grapefruits.

MANAGEMENT: Patients treated with ixabepilone should avoid the consumption of grapefruit or grapefruit juice.