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Chemical compound
AA560
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Other names | AA-560; N-(2-Chloromethyl-2-hydroxypropionyl)-3,4,5-trichloroaniline |
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Routes of administration |
By mouth
[1] |
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Drug class |
Nonsteroidal antiandrogen |
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2-Hydroxy-2-methyl-N-(3,4,5-trichlorophenyl)propanamide
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CAS Number | |
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PubChem
CID | |
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ChemSpider | |
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UNII | |
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CompTox Dashboard (
EPA) | |
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Formula | C10H10Cl3NO2 |
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Molar mass | 282.55 g·mol−1 |
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3D model (
JSmol) | |
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CC(C)(C(=O)NC1=CC(=C(C(=C1)Cl)Cl)Cl)O
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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
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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]
See also
References
- ^
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.
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^ 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.
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^ 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.
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ARTooltip Androgen receptor | Agonists | |
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SARMsTooltip Selective androgen receptor modulator | |
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Antagonists | |
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GPRC6A | |
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