Chemistry:Azacosterol
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| Other names | 20,25-Diazacholesterol; 20,25-Azacholesterol; Azasterol; Diazasterol; SC-12937; DAC; IMD-760; 17β-(3-(Dimethylamino)propyl)methyl- amino)androst-5-en-3β-ol |
| Routes of administration | By mouth |
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| Formula | C25H44N2O |
| Molar mass | 388.640 g·mol−1 |
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Azacosterol (INN), or azacosterol hydrochloride (USAN) (brand name Ornitrol), also known as 20,25-diazacholesterol, is a cholesterol-lowering drug (hypocholesteremic), which was marketed previously, but has since been discontinued.[1][2][3] It is also an avian chemosterilant used to control pest pigeon populations via inducing sterility.[4] The drug is a sterol and derivative of cholesterol in which two carbon atoms have been replaced with nitrogen atoms.[5]
Azacosterol acts as an inhibitor of 24-dehydrocholesterol reductase (24-DHCR), preventing the formation of cholesterol from desmosterol.[4][6] Although it primarily acts to inhibit 24-DHCR, the drug also inhibits other steps in cholesterol biosynthesis.[6] The antifertility effects of the drug in birds are mediated by inhibition of steroid hormone production, steroid hormones being synthesized from cholesterol.[4] Due to prevention of the metabolism of desmosterol, the drug causes it to accumulate, in turn producing side effects such as hyperkeratosis, particularly of the palms and soles.[6]
See also
- Desmosterolosis
- Triparanol
- X-linked ichthyosis
References
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 110–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA110.
- ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 31 October 1999. pp. 43–. ISBN 978-0-7514-0499-9. https://books.google.com/books?id=mqaOMOtk61IC&pg=PA43.
- ↑ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 463–. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA463.
- ↑ 4.0 4.1 4.2 "Heterosteroids and drug research". Progress in Medicinal Chemistry 16: 35–149. January 1979. doi:10.1016/s0079-6468(08)70187-5. ISBN 9780720406672. PMID 95596. https://books.google.com/books?id=wesIAirSEDkC&pg=PA79.
- ↑ "Hypocholesterolemic Agents. III.1N-Methyl-N-(dialkylamino)alkyl-17β-aminoandrost-5-en-3β-ol Derivatives". Journal of Medicinal and Pharmaceutical Chemistry 91 (6): 1224–33. November 1962. doi:10.1021/jm01241a014. PMID 14056455.
- ↑ 6.0 6.1 6.2 "Lipids in normal and pathological desquamation". Advances in Lipid Research: Skin Lipids. Elsevier. 21 January 2016. pp. 218–220. ISBN 978-1-4832-1545-7. https://books.google.com/books?id=rTeaBQAAQBAJ&pg=PA218.
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