Structural Formula Vector Image
Title: Ixabepilone
CAS Registry Number: 219989-84-1
CAS Name: (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione
Additional Names: azaepothilone B
Manufacturers' Codes: BMS-247550; NSC-710428
Molecular Formula: C27H42N2O5S
Molecular Weight: 506.70
Percent Composition: C 64.00%, H 8.35%, N 5.53%, O 15.79%, S 6.33%
Literature References: Microtubule stabilizing semisynthetic lactam analog of epothilone B, q.v. Prepn: G. D. Vite et al., WO 9902514; eidem, US 6605599 (1999, 2003 both to Bristol-Myers Squibb); R. M. Borzilleri et al., J. Am. Chem. Soc. 122, 8890 (2000). Antineoplastic activity in vitro and in vivo: F. Y. F. Lee et al., Clin. Cancer Res. 7, 1429 (2001). Clinical evaluation with estramustine in prostate cancer: J. E. Rosenberg et al., Cancer 106, 58 (2006). Clinical pharmacokinetics and evaluation in solid tumors: S. Mani et al., Clin. Cancer Res. 10, 1289 (2004). Clinical evaluation in breast cancer: J. A. Low et al., J. Clin. Oncol. 23, 2726 (2005); in prostate cancer: M. Hussain et al., ibid. 8724. Review of pharmacology and clinical development: N. Lin et al., Curr. Opin. Invest. Drugs 4, 746-756 (2003).
Properties: Colorless oil or white lyopholizate; [a]D22 -40.7° (c = 1.0 in chloroform).
Optical Rotation: [a]D22 -40.7° (c = 1.0 in chloroform)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products.

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