AC-262,536

AC-262,536
Identifiers
	IUPAC name 4-[(1R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]naphthalene-1-carbonitrile;
CAS Number	870888-46-3 ; 871032-12-1 (exo form);
PubChem CID	44512434;
ChemSpider	31129035;
UNII	U8VS41J5O6;
ChEMBL	ChEMBL3084525;
CompTox Dashboard (EPA)	DTXSID201028423 ;
Chemical and physical data
Formula	C18H18N2O
Molar mass	278.355 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC1C[C@@H]2CC[C@H](C1)N2c3ccc(C#N)c4ccccc34;
	InChI 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 K_i 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.

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Identifiers

IUPAC name 4-[(1R,3S,5S)-3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]naphthalene-1-carbonitrile
CAS Number	870888-46-3 871032-12-1 (exo form)
PubChem CID	44512434
ChemSpider	31129035
UNII	U8VS41J5O6
ChEMBL	ChEMBL3084525
CompTox Dashboard (EPA)	DTXSID201028423
Chemical and physical data
Formula	C₁₈H₁₈N₂O
Molar mass	278.355 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES OC1C[C@@H]2CC[C@H](C1)N2c3ccc(C#N)c4ccccc34
InChI 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)