Azacosterol

Last updated
Azacosterol
Azacholesterol.png
Azacosterol molecule ball.png
Clinical data
Other names20,25-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
Identifiers
  • (3S,8R,9S,10R,13S,14S,17S)-17-[3-(dimethylamino)propyl-methylamino]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C25H44N2O
Molar mass 388.640 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2N(C)CCCN(C)C)CC=C4[C@@]3(CC[C@@H](C4)O)C
  • InChI=1S/C25H44N2O/c1-24-13-11-19(28)17-18(24)7-8-20-21-9-10-23(25(21,2)14-12-22(20)24)27(5)16-6-15-26(3)4/h7,19-23,28H,6,8-17H2,1-5H3/t19-,20-,21-,22-,23-,24-,25-/m0/s1 Yes check.svgY
  • Key:FMTFZYKYVZBISL-HUVRVWIJSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Azacosterol (INN Tooltip International Nonproprietary Name), or azacosterol hydrochloride (USAN Tooltip United States Adopted Name) (brand name Ornitrol), also called 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

References

  1. ↑ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 110–. ISBN   978-1-4757-2085-3.
  2. ↑ Morton IK, Hall JM (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 43–. ISBN   978-0-7514-0499-9.
  3. ↑ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 463–. ISBN   978-0-8155-1856-3.
  4. 1 2 3 Singh H, Kapoor VK, Paul D (January 1979). "Heterosteroids and drug research" . Progress in Medicinal Chemistry. 16: 35–149. doi:10.1016/s0079-6468(08)70187-5. ISBN   9780720406672. PMID   95596.
  5. ↑ Counsell RE, Klimstra PD, Ranney RE (November 1962). "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. doi:10.1021/jm01241a014. PMID   14056455.
  6. 1 2 3 Williams ML (21 January 2016). "Lipids in normal and pathological desquamation". In Elias PM (ed.). Advances in Lipid Research: Skin Lipids. Elsevier. pp. 218–220. ISBN   978-1-4832-1545-7.


This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.