AA560 information

AA560
Clinical data
Other names	AA-560; N-(2-Chloromethyl-2-hydroxypropionyl)-3,4,5-trichloroaniline
Routes of; administration	By mouth
Drug class	Nonsteroidal antiandrogen
Identifiers
	IUPAC name 2-Hydroxy-2-methyl-N-(3,4,5-trichlorophenyl)propanamide;
CAS Number	65372-80-7 ;
PubChem CID	125204;
ChemSpider	111441;
UNII	3HS29B4W75;
CompTox Dashboard (EPA)	DTXSID80983988 ;
Chemical and physical data
Formula	C10H10Cl3NO2
Molar mass	282.55 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

^ ^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.
^ ^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.
^ 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.
^ 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.

[ShidaYamanaka1980-1] 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.

[YamanakaKoya1981-2] 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.

[pmid10637363-3] 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.

[AcademicPress1986-4] 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.

AA560 information

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Clinical data

Other names	AA-560; N-(2-Chloromethyl-2-hydroxypropionyl)-3,4,5-trichloroaniline
Routes of administration	By mouth^[1]
Drug class	Nonsteroidal antiandrogen
Identifiers
IUPAC name 2-Hydroxy-2-methyl-N-(3,4,5-trichlorophenyl)propanamide
CAS Number	65372-80-7^Y
PubChem CID	125204
ChemSpider	111441
UNII	3HS29B4W75
CompTox Dashboard (EPA)	DTXSID80983988
Chemical and physical data
Formula	C₁₀H₁₀Cl₃NO₂
Molar mass	282.55 g·mol⁻¹
3D model (JSmol)	Interactive image
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