Azacosterol

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 the pest pigeon population 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

Clinical data
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
Identifiers
IUPAC name (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	313-05-3 1249-84-9 (hydrochloride)
PubChem CID	10023199
ChemSpider	8198772
UNII	EPT876J73A
ChEMBL	ChEMBL1615357
CompTox Dashboard (EPA)	DTXSID1058509
Chemical and physical data
Formula	C25H44N2O
Molar mass	388.640 g·mol^−1
3D model (JSmol)	Interactive image
SMILES 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 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 Key:FMTFZYKYVZBISL-HUVRVWIJSA-N
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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 anti-fertility 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

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 I, 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. Progress in Medicinal Chemistry. Elsevier. 1 January 1979. pp. 79–. ISBN 978-0-08-086264-4.
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. Elias PM (21 January 2016). Advances in Lipid Research: Skin Lipids. Elsevier. pp. 218–220. ISBN 978-1-4832-1545-7.