AC-262,536

AC-262,536
Identifiers
  • 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)
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, also known as Accadrine, 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] The drug was encountered as a novel designer drug by at least 2020.[5]

Medical uses

Accadrine is not approved for any medical use by the Food and Drug Administration and is not available as a licensed pharmaceutical drug as of 2025.[6]

Pharmacology

Pharmacodynamics

Accadrine is selective androgen receptor modulator (SARM), or a tissue-selective mixed agonist or partial agonist of the androgen receptor (AR).[7][4] This receptor is the biological target of endogenous androgens like testosterone and dihydrotestosterone (DHT) and of synthetic anabolic steroids like nandrolone and oxandrolone.[8][9][10][11] Accadrine shows high affinity for the AR, with a Ki value of 5 nM (relative to 29 nM for testosterone and 10 nM for DHT).[1][2][3]

References

  1. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b 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.
  5. ^ "AC-262,536". АИПСИН (in Russian). Retrieved 2 January 2026.
  6. ^ "FDA warns against using SARMs in body-building products". U.S. Food and Drug Administration. Food and Drug Administration. October 31, 2017. Retrieved 2025-12-08.
  7. ^ Machek SB, Cardaci TD, Wilburn DT, Willoughby DS (December 2020). "Considerations, possible contraindications, and potential mechanisms for deleterious effect in recreational and athletic use of selective androgen receptor modulators (SARMs) in lieu of anabolic androgenic steroids: A narrative review". Steroids. 164 108753. doi:10.1016/j.steroids.2020.108753. PMID 33148520. S2CID 225049089.
  8. ^ Handelsman DJ (5 October 2020). "Androgen Physiology, Pharmacology, Use and Misuse". In Feingold KR, Anawalt B, Blackman MR, Boyce A, Chrousos G, Corpas E, et al. (eds.). Endotext [Internet]. South Dartmouth (MA): MDText.com, Inc. PMID 25905231.
  9. ^ Wu C, Kovac JR (October 2016). "Novel Uses for the Anabolic Androgenic Steroids Nandrolone and Oxandrolone in the Management of Male Health". Current Urology Reports. 17 (10): 72. doi:10.1007/s11934-016-0629-8. PMID 27535042. S2CID 43199715.
  10. ^ Mohler ML, Nair VA, Hwang DJ, Rakov IM, Patil R, Miller DD (2005-10-28). "Nonsteroidal tissue selective androgen receptor modulators: a promising class of clinical candidates". Expert Opinion on Therapeutic Patents. 15 (11). Informa Healthcare: 1565–1585. doi:10.1517/13543776.15.11.1565. ISSN 1354-3776. S2CID 96279138.
  11. ^ Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
allikas: https://en.wikipedia.org/wiki/AC-262,536