10337. Abiraterone

Nomenclature

CAS number: 154229-19-3
(3β)-17-(3-Pyridinyl)androsta-5,16-dien-3-ol; 17-(3-pyridyl)androsta-5,16-dien-3β-ol; CB-7598.
C24H31NO; mol wt 349.51.
C 82.47%, H 8.94%, N 4.01%, O 4.58%.

Description and references

Androgen biosynthesis inhibitor; inhibits cytochrome P450c17 (17α-hydroxylase-C17,20-lyase). Prepn: S. E. Barrie et al., WO 9320097, idem et al., US 5604213 (1993, 1997 both to British Technol. Group); G. A. Potter et al., J. Med. Chem. 38, 2463 (1995) DOI PubMed. LC-MS/MS determn in plasma: V. Martins et al., J. Chromatogr. B 843, 262 (2006) DOI PubMed. Clinical pharmacokinetics and hormonal effects: A. O'Donnell et al., Br. J. Cancer 90, 2317 (2004) DOI PubMed. Clinical evaluation in resistant prostate cancer: G. Attard et al., J. Clin. Oncol. 26, 4563 (2008) DOI PubMed. Review of mechanism of action: G. Attard et al., BJU Int. 96, 1241-1246 (2005) DOI PubMed; of development: R. Aggarwal, D. J. Ryan, Update Cancer Ther. 2, 171-175 (2007) DOI.

Chemical structure

Properties

Crystals from toluene, mp 228-229°.

Derivative

Acetate.

Nomenclature

CAS number: 154229-18-2
(3β)-Acetoxy-17-(3-pyridyl)androsta-5,16-diene; CB-7630.
C26H33NO2; mol wt 391.55.
C 79.75%, H 8.49%, N 3.58%, O 8.17%.

Description and references

Large-scale synthesis: G. A. Potter et al., Org. Prep. Proced. Int. 29, 123 (1997).

Properties

Crystals from acetonitrile, mp 146-148°.

Therapeutic Category

Antineoplastic (hormonal).

Keywords

Antineoplastic (Hormonal); Antiandrogens