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AA560

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
AA560
Clinical data
Other namesAA-560; N-(2-Chloromethyl-2-hydroxypropionyl)-3,4,5-trichloroaniline
Routes of
administration		By mouth[1]
Drug classNonsteroidal antiandrogen
Identifiers
  • 2-Hydroxy-2-methyl-N-(3,4,5-trichlorophenyl)propanamide
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC10H10Cl3NO2
Molar mass282.55 g·mol−1
3D model (JSmol)
  • CC(C)(C(=O)NC1=CC(=C(C(=C1)Cl)Cl)Cl)O
  • InChI=1S/C10H10Cl3NO2/c1-10(2,16)9(15)14-5-3-6(11)8(13)7(12)4-5/h3-4,16H,1-2H3,(H,14,15)
  • Key:FVEPMRZJQUYLRA-UHFFFAOYSA-N

AA560 is anorally activenonsteroidal antiandrogen (NSAA) that was developed inJapan and was first described in the literature in 1977 but was never marketed.[1][2][3] It is ananilidederivative andanalogue of the NSAAflutamide, and shows greaterin vivo antiandrogenicpotency than does flutamide.[1][2] Similarly to flutamide, AA560 is aselectiveantagonist of theandrogen receptor (AR) and consequently showsprogonadotropic effects by increasing levels ofgonadotropins andtestosterone via disinhibition of thehypothalamic-pituitary-gonadal axis.[1][2][4]

See also

[edit]

References

[edit]
  1. ^abcdShida K, Yamanaka H, Koya A, Wakabayashi K, Mori H, Shibata K, Shimazawa E (February 1980)."Action of a novel nonsteroidal antiandrogen, AA560".Endocrinologia Japonica.27 (1):69–76.doi:10.1507/endocrj1954.27.69.PMID 6156070.
  2. ^abcYamanaka H, Koya A, Imai K, Nakai K, Yuasa H, Sugiyama Y, et al. (December 1981)."Effect of AA560 (a nonsteroidal antiandrogen) implantation in the hypothalamus on gonadotropin secretion in male rats".Endocrinologia Japonica.28 (6):819–822.doi:10.1507/endocrj1954.28.819.PMID 6809452.
  3. ^Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships".Current Medicinal Chemistry.7 (2):211–247.doi:10.2174/0929867003375371.PMID 10637363.
  4. ^Rasmusson GH (September 1986)."Chemical Control of Androgen Action.".Annual Reports in Medicinal Chemistry. Vol. 21. Academic Press. pp. 179-188 (181).ISBN 978-0-08-058365-5.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists


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