Azacosterol

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 (INNTooltip International Nonproprietary Name), or azacosterol hydrochloride (USANTooltip United States Adopted Name) (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]

References

^ 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.
^ 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.
^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 463–. ISBN 978-0-8155-1856-3.
^ ^a ^b ^c 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.
^ 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.
^ ^a ^b ^c 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.

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[Elks2014-1] 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.

[MortonHall1999-2] 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.

[Publishing2013-3] William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 463–. ISBN 978-0-8155-1856-3.

[Elsevier1979-4] 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.

[pmid14056455-5] 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.

[Williams_2016-6] 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.

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See also

References