S-23 (drug)

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S-23
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Systematic (IUPAC) name
(2S)-N-(4-cyano-3-trifluoromethylphenyl)-3-(3-fluoro-4-chlorophenoxy)-2-hydroxy-2-methyl-propanamide
Clinical data
Legal status
  • Investigational new drug
Identifiers
PubChem CID: 24892822
DrugBank DB07419 YesY
ChemSpider 24715019
UNII XDK89456WM YesY
Chemical data
Formula C18H13ClF4N2O3
Molecular mass 416.753 g/mol
  • C[C@](COC1=CC(=C(C=C1)Cl)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
  • InChI=1S/C18H13ClF4N2O3/c1-17(27,9-28-12-4-5-14(19)15(20)7-12)16(26)25-11-3-2-10(8-24)13(6-11)18(21,22)23/h2-7,27H,9H2,1H3,(H,25,26)/t17-/m0/s1
  • Key:SSFVOEAXHZGTRJ-KRWDZBQOSA-N
  (verify)

S-23 is an investigational selective androgen receptor modulator (SARM) developed by GTX, Inc as a potential male hormonal contraceptive. It binds to the androgen receptor more strongly than older drugs such as andarine with a Ki of 1.7nM, and in animal studies it showed both a good ratio of anabolic to androgenic effects, and dose-dependent suppression of spermatogenesis with spontaneous recovery after cessation of treatment.[1][2]

References

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  1. ↑ Marhefka CA, Gao W, Chung K, Kim J, He Y, Yin D, Bohl C, Dalton JT, Miller DD. Design, synthesis, and biological characterization of metabolically stable selective androgen receptor modulators. Journal of Medicinal Chemistry. 2004 Feb 12;47(4):993-8. PMID 14761201
  2. ↑ Jones A, Chen J, Hwang DJ, Miller DD, Dalton JT. Preclinical characterization of a (S)-N-(4-cyano-3-trifluoromethyl-phenyl)-3-(3-fluoro, 4-chlorophenoxy)-2-hydroxy-2-methyl-propanamide: a selective androgen receptor modulator for hormonal male contraception. Endocrinology. 2009 Jan;150(1):385-95. doi:10.1210/en.2008-0674 PMID 18772237
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