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AA560

Summary

AA560 is an orally active nonsteroidal antiandrogen (NSAA) that was developed in Japan and was first described in the literature in 1977 but was never marketed.[1][2][3] It is an anilide derivative and analogue of the NSAA flutamide, and shows greater in vivo antiandrogenic potency than does flutamide.[1][2] Similarly to flutamide, AA560 is a selective antagonist of the androgen receptor (AR) and consequently shows progonadotropic effects by increasing levels of gonadotropins and testosterone via disinhibition of the hypothalamic-pituitary-gonadal axis.[1][2][4]

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
  • 65372-80-7 checkY
PubChem CID
  • 125204
ChemSpider
  • 111441
UNII
  • 3HS29B4W75
CompTox Dashboard (EPA)
  • DTXSID80983988 Edit this at Wikidata
Chemical and physical data
FormulaC10H10Cl3NO2
Molar mass282.55 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

See also edit

References edit

  1. ^ a b c d Shida 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. ^ a b c Yamanaka 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.