From Wikipedia, the free encyclopedia
Chemical compound
AC-262,536
4-[(1R ,3S ,5S )-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]naphthalene-1-carbonitrile
CAS Number
PubChem
CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (
EPA )
Formula C 18 H 18 N 2 O
Molar mass 278.355 g·mol−1 3D model (
JSmol )
OC1C[C@@H]2CC[C@H](C1)N2c3ccc(C#N)c4ccccc34
InChI=1S/C18H18N2O/c19-11-12-5-8-18(17-4-2-1-3-16(12)17)20-13-6-7-14(20)10-15(21)9-13/h1-5,8,13-15,21H,6-7,9-10H2/t13-,14+,15+
Key:ATKWLNSCJYLXPF-FICVDOATSA-N
(verify)
AC-262536 is a drug developed by
Acadia Pharmaceuticals which acts as a
selective androgen receptor modulator (SARM). Chemically it possesses
endo-exo isomerism , with the endo form being the active form. It acts as a
partial agonist for the
androgen receptor with a
Ki of 5 nM, and no significant affinity for any other receptors tested. In animal studies it produced a maximal effect of around 66% of the
levator ani
muscle weight increase of
testosterone , but only around 27% of its maximal effect on
prostate gland weight.
[1]
[2]
[3] It is an
aniline SARM related to
ACP-105 and
vosilasarm (RAD140).
[4]
References
^ Piu F, Gardell LR, Son T, Schlienger N, Lund BW, Schiffer HH, Vanover KE, Davis RE, Olsson R, Bradley SR (March 2008). "Pharmacological characterization of AC-262536, a novel selective androgen receptor modulator". J Steroid Biochem Mol Biol . 109 (1–2): 129–37.
doi :
10.1016/j.jsbmb.2007.11.001 .
PMID
18164613 .
S2CID
25172405 .
^ Cutler C, Viljanto M, Taylor P, Habershon-Butcher J, Muir T, Biddle S, Van Eenoo P (February 2021).
"Equine metabolism of the selective androgen receptor modulator AC-262536 in vitro and in urine, plasma and hair following oral administration" . Drug Testing and Analysis . 13 (2): 369–385.
doi :
10.1002/dta.2932 .
hdl :
1854/LU-8694577 .
PMID
32959959 .
S2CID
221842707 .
^ Stacchini C, Botrè F, Comunità F, de la Torre X, Dima AP, Ricci M, Mazzarino M (February 2021). "Simultaneous detection of different chemical classes of selective androgen receptor modulators in urine by liquid chromatography-mass spectrometry-based techniques". Journal of Pharmaceutical and Biomedical Analysis . 195 : 113849.
doi :
10.1016/j.jpba.2020.113849 .
PMID
33383501 .
S2CID
229941017 .
^ Zhang X, Sui Z (February 2013). "Deciphering the selective androgen receptor modulators paradigm". Expert Opinion on Drug Discovery . 8 (2): 191–218.
doi :
10.1517/17460441.2013.741582 .
PMID
23231475 .
S2CID
2584722 .
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A