{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = | verifiedrevid = 460324027 | IUPAC_name = (3''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-[3-(dimethylamino)propyl-methylamino]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1''H''-cyclopenta[''a'']phenanthren-3-ol | image = Azacholesterol.png | image_class = skin-invert-image | width = 250px | image2 = Azacosterol molecule ball.png | image_class2 = bg-transparent | width2 = 250px | alt2 = Ball-and-stick model of azacosterol
<!--Clinical data--> | tradename = | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 313-05-3 | CAS_supplemental = <br />1249-84-9 (hydrochloride) | class = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 10023199 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8198772 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = EPT876J73A | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1615357 | synonyms = 20,25-Diazacholesterol; 20,25-Azacholesterol; Azasterol; Diazasterol; SC-12937; DAC; IMD-760; 17β-(3-(Dimethylamino)propyl)methyl-<br />amino)androst-5-en-3β-ol
<!--Chemical data--> | C=25 | H=44 | N=2 | O=1 | 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 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FMTFZYKYVZBISL-HUVRVWIJSA-N }}
'''Azacosterol''' ({{Abbrlink|INN|International Nonproprietary Name}}), or '''azacosterol hydrochloride''' ({{Abbrlink|USAN|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.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA110|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=110–}}</ref><ref name="MortonHall1999">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=mqaOMOtk61IC&pg=PA43|date=31 October 1999|publisher=Springer Science & Business Media|isbn=978-0-7514-0499-9|pages=43–}}</ref><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia | edition = 3rd |url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA463|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=463–}}</ref> It is also an avian chemosterilant used to control pest pigeon populations via inducing sterility.<ref name="Elsevier1979">{{cite journal | vauthors = Singh H, Kapoor VK, Paul D | title = Heterosteroids and drug research | journal = Progress in Medicinal Chemistry | volume = 16 | issue = | pages = 35–149 | date = January 1979 | pmid = 95596 | doi = 10.1016/s0079-6468(08)70187-5 | isbn = 9780720406672 | url = https://books.google.com/books?id=wesIAirSEDkC&pg=PA79 | url-access = subscription }}</ref> The drug is a sterol and derivative of cholesterol in which two carbon atoms have been replaced with nitrogen atoms.<ref name="pmid14056455">{{cite journal | vauthors = Counsell RE, Klimstra PD, Ranney RE | title = Hypocholesterolemic Agents. III.1N-Methyl-N-(dialkylamino)alkyl-17β-aminoandrost-5-en-3β-ol Derivatives | journal = Journal of Medicinal and Pharmaceutical Chemistry | volume = 91 | issue = 6 | pages = 1224–33 | date = November 1962 | pmid = 14056455 | doi = 10.1021/jm01241a014 }}</ref>
Azacosterol acts as an inhibitor of 24-dehydrocholesterol reductase (24-DHCR), preventing the formation of cholesterol from desmosterol.<ref name="Elsevier1979" /><ref name="Williams_2016">{{cite book| vauthors = Williams ML | chapter = Lipids in normal and pathological desquamation | veditors = Elias PM |title=Advances in Lipid Research: Skin Lipids|chapter-url=https://books.google.com/books?id=rTeaBQAAQBAJ&pg=PA218|date=21 January 2016|publisher=Elsevier|isbn=978-1-4832-1545-7|pages=218–220}}</ref> Although it primarily acts to inhibit 24-DHCR, the drug also inhibits other steps in cholesterol biosynthesis.<ref name="Williams_2016" /> The antifertility effects of the drug in birds are mediated by inhibition of steroid hormone production, steroid hormones being synthesized from cholesterol.<ref name="Elsevier1979" /> 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.<ref name="Williams_2016" />
==See also== * Desmosterolosis * Triparanol * X-linked ichthyosis
==References== {{Reflist}}
{{Lipid modifying agents}}
Category:24-Dehydrocholesterol reductase inhibitors Category:Lipid-lowering agents Category:Sterols Category:Withdrawn drugs
{{Cardiovascular-drug-stub}}