Azacosterol

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Azacosterol
File:Azacholesterol.png
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
  • (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
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC25H44N2O
Molar mass388.640 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 checkY
  • Key:FMTFZYKYVZBISL-HUVRVWIJSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Azacosterol (INNTooltip International Nonproprietary Name), or azacosterol hydrochloride (USANTooltip 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

[edit | edit source]

References

[edit | edit source]
  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  4. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  5. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  6. ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).


Stub icon

This drug article relating to the cardiovascular system is a stub. You can help Wikipedia by expanding it.

Retrieved from "http://70.231.62.181/index.php?title=Azacosterol&oldid=17164172"