AA560

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
IUPAC name
  • 2-Hydroxy-2-methyl-N-(3,4,5-trichlorophenyl)propanamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H10Cl3NO2
Molar mass282.55 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)(C(=O)NC1=CC(=C(C(=C1)Cl)Cl)Cl)O
InChI
  • 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

References
  1. Shida, Keizo; Yamanaka, Hidetoshi; Koya, Atsushi; Wakabayashi, Katsumi; Mori, Hiroshi; Shibata, Kenyu; Shimazawa, Eiichiro (1980). "Action of a novel nonsteroidal antiandrogen, AA560". Endocrinologia Japonica. 27 (1): 69–76. doi:10.1507/endocrj1954.27.69. ISSN 0013-7219. PMID 6156070.
  2. Yamanaka, Hidetoshi; Koya, Atsushi; Imai, Kyoichi; Nakai, Katsuyuki; Yuasa, Hisako; Sugiyama, Yuko; Shida, Keizo; Wakabayashi, Katsumi (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. ISSN 0013-7219. PMID 6809452.
  3. Singh SM, Gauthier S, Labrie F (2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Curr. Med. Chem. 7 (2): 211–47. doi:10.2174/0929867003375371. PMID 10637363.
  4. Annual Reports in Medicinal Chemistry. Academic Press. 16 September 1986. pp. 181–. ISBN 978-0-08-058365-5.


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