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AC-262,536

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
AC-262,536
Identifiers
  • 4-[(1R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]naphthalene-1-carbonitrile
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H18N2O
Molar mass278.355 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 byAcadia Pharmaceuticals which acts as aselective androgen receptor modulator (SARM). Chemically it possessesendo-exo isomerism, with the endo form being the active form. It acts as apartial agonist for theandrogen receptor with aKi of 5 nM, and no significant affinity for any other receptors tested. In animal studies it produced a maximal effect of around 66% of thelevator animuscle weight increase oftestosterone, but only around 27% of its maximal effect onprostate gland weight.[1][2][3] It is ananiline SARM related toACP-105 andvosilasarm (RAD140).[4]

References

[edit]
  1. ^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.
  2. ^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.
  3. ^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.
  4. ^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.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists


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