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. https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA183.
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. https://books.google.com/books?id=Ex3NvHbC8yEC&pg=PA321.
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 et al. (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. et al. (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.

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Steroid classification

C17|

* Gonane

C18|

* Estrane: Dehydrogenated: Estrene
* Estradiene
* Estratriene; Substituted: Estratrienolone
* Estratrienediol
* Estratrienetriol

C19|

* Androstane: Dehydrogenated: Androstene
* Androstadiene
* Androstatriene; Substituted: Androstanol
* Androstenol
* Androstanone
* Androstenone
* Androstanediol
* Androstenediol
* Androstanedione
* Androstenedione
* Androstenetrione
* Androstanolone
* Androstenolone
* Androstadienol
* Androstadienone; Etiocholane

C20|

* 19-Norpregnane

C21|

* Pregnane: Dehydrogenated: Pregnene
* Pregnadiene
* Pregnatriene; Substituted: Pregnanediol
* Pregnanetriol
* Pregnenediol
* Pregnanedione
* Pregnenedione
* 5α-Pregnane
* 5β-Pregnane

C23|

* Cardanolide

C24|

* Cholane
* Bile acid

C27|

* Cholestane

Functional group|

* 17-Ketosteroid
* Hydroxysteroid
* Halogenated steroid

Elements removed|

* Norsteroid
* Secosteroid

Elements replaced|

* Azasteroid

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