AC-262,536

{{short description|Chemical compound}}

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{{Drugbox

| verifiedrevid = 448229525

| IUPAC_name = 4-[(1R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]naphthalene-1-carbonitrile

| image = AC-262,356.svg

| width = 250px

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| CAS_number = 870888-46-3

| CAS_supplemental =
871032-12-1 (exo form)

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| PubChem = 44512434

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = U8VS41J5O6

| ChemSpiderID = 31129035

| ChEMBL = 3084525

| C=18 | H=18 | N=2 | O=1

| SMILES = OC1C[C@@H]2CC[C@H](C1)N2c3ccc(C#N)c4ccccc34

| StdInChI = 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+

| StdInChIKey = ATKWLNSCJYLXPF-FICVDOATSA-N

}}

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 K_i of 5{{nbsp}}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.{{cite journal | vauthors = Piu F, Gardell LR, Son T, Schlienger N, Lund BW, Schiffer HH, Vanover KE, Davis RE, Olsson R, Bradley SR | title = Pharmacological characterization of AC-262536, a novel selective androgen receptor modulator | journal = J Steroid Biochem Mol Biol | volume = 109 | issue = 1–2 | pages = 129–37 | date = March 2008 | pmid = 18164613 | doi = 10.1016/j.jsbmb.2007.11.001 | s2cid = 25172405 | url = }}{{cite journal | vauthors = Cutler C, Viljanto M, Taylor P, Habershon-Butcher J, Muir T, Biddle S, Van Eenoo P | title = Equine metabolism of the selective androgen receptor modulator AC-262536 in vitro and in urine, plasma and hair following oral administration | journal = Drug Testing and Analysis | volume = 13 | issue = 2 | pages = 369–385 | date = February 2021 | pmid = 32959959 | doi = 10.1002/dta.2932 | hdl = 1854/LU-8694577 | s2cid = 221842707 | url = https://biblio.ugent.be/publication/8694577 | hdl-access = free }}{{cite journal | vauthors = Stacchini C, Botrè F, Comunità F, de la Torre X, Dima AP, Ricci M, Mazzarino M | title = Simultaneous detection of different chemical classes of selective androgen receptor modulators in urine by liquid chromatography-mass spectrometry-based techniques | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 195 | pages = 113849 | date = February 2021 | pmid = 33383501 | doi = 10.1016/j.jpba.2020.113849 | s2cid = 229941017 }} It is an aniline SARM related to ACP-105 and vosilasarm (RAD140).{{cite journal | vauthors = Zhang X, Sui Z | title = Deciphering the selective androgen receptor modulators paradigm | journal = Expert Opinion on Drug Discovery | volume = 8 | issue = 2 | pages = 191–218 | date = February 2013 | pmid = 23231475 | doi = 10.1517/17460441.2013.741582 | s2cid = 2584722 }}