Azasteroid

An azasteroid is a type of steroid derivative which has one of the carbon atoms in the steroid ring system replaced by a nitrogen atom. Two azasteroids, finasteride and dutasteride, are used clinically as 5α-reductase inhibitors.[1][2][3]

Finasteride and dutasteride, two azasteroid pharmaceutical drugs. The nitrogen atoms in each ring system are highlighted in red.

Some of the 6-azasteroids may prove to be useful drugs, but have yet to reach the pharmaceutical market.[4][5]

References

1. Enrique Ravina (11 January 2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. pp. 183–. ISBN 978-3-527-32669-3.
2. Roger S. Kirby; John D. McConnell; John M. Fitzpatrick; Claus G. Roehrborn; Peter Boyle (29 November 2004). Textbook of Benign Prostatic Hyperplasia, Second Edition. CRC Press. pp. 321–. ISBN 978-1-901865-55-4.
3. Singh, Shankar; Gauthier, Sylvain; Labrie, Fernand (2000). "Androgen Receptor Antagonists (Antiandrogens) Structure-Activity Relationships". Current Medicinal Chemistry. 7 (2): 211–247. doi:10.2174/0929867003375371. ISSN 0929-8673. PMID 10637363.
4. Frye, Stephen V.; Haffner, Curt D.; Maloney, Patrick R.; Mook, Robert A.; Dorsey, G. F.; Hiner, Roger N.; Batchelor, Kenneth W.; Bramson, H. Neal; Stuart, J. Darren (1993). "6-Azasteroids: Potent dual inhibitors of human type 1 and 2 steroid 5.alpha.-reductase". Journal of Medicinal Chemistry. 36 (26): 4313–5. doi:10.1021/jm00078a022. PMID 8277514.
5. Frye, Stephen V.; Haffner, Curt D.; Maloney, Patrick R.; Mook, Robert A.; Dorsey, George F.; Hiner, Roger N.; Cribbs, Cindy M.; Wheeler, Thomas N.; Ray, John A. (1994). "6-Azasteroids: Structure-Activity Relationships for Inhibition of Type 1 and 2 Human 5.alpha.-Reductase and Human Adrenal 3.beta.-Hydroxy-.DELTA.5-steroid Dehydrogenase/3-Keto-.DELTA.5-steroid Isomerase". Journal of Medicinal Chemistry. 37 (15): 2352–60. doi:10.1021/jm00041a014. PMID 8057283.