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Azacosterol

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(Redirected from Ornitrol) Chemical compound Pharmaceutical compound
Azacosterol
Ball-and-stick model of azacosterol
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
IUPAC name
  • (3S,8R,9S,10R,13S,14S,17S)-17--10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopentaphenanthren-3-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H44N2O
Molar mass388.640 g·mol
3D model (JSmol)
SMILES
  • C12CC3(1CC2N(C)CCCN(C)C)CC=C43(CC(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
  (what is this?)  (verify)

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. It is also an avian chemosterilant used to control pest pigeon populations via inducing sterility. The drug is a sterol and derivative of cholesterol in which two carbon atoms have been replaced with nitrogen atoms.

Azacosterol acts as an inhibitor of 24-dehydrocholesterol reductase (24-DHCR), preventing the formation of cholesterol from desmosterol. Although it primarily acts to inhibit 24-DHCR, the drug also inhibits other steps in cholesterol biosynthesis. The antifertility effects of the drug in birds are mediated by inhibition of steroid hormone production, steroid hormones being synthesized from cholesterol. 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.

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. ^ 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. ^ 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.


Lipid-lowering agents (C10)
GI tract
Cholesterol absorption inhibitors, NPC1L1
Bile acid sequestrants/resins (LDL)
Liver
Statins (HMG-CoA reductase, LDL)
Niacin and derivatives (HDL and LDL)
MTTP inhibitors (VLDL)
ATP citrate lyase inhibitors (LDL)
Thyromimetics (VLDL)
Blood vessels
PPAR agonists (LDL)
Fibrates
Others
CETP inhibitors (HDL)
PCSK9 inhibitors (LDL)
ANGPTL3 inhibitors (LDL/HDL)
Combinations
Other
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