S-23 (drug)

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 1.7 nM, 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]

S-23
Legal status
Legal status
Identifiers
IUPAC name
  • (2S)-N-(4-cyano-3-trifluoromethylphenyl)-3-(3-fluoro-4-chlorophenoxy)-2-hydroxy-2-methyl-propanamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
Chemical and physical data
FormulaC18H13ClF4N2O3
Molar mass416.76 g·mol−1
3D model (JSmol)
SMILES
  • C[C@](COC1=CC(=C(C=C1)Cl)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
InChI
  • 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 N
  • Key:SSFVOEAXHZGTRJ-KRWDZBQOSA-N N
 NY (what is this?)  (verify)

References
  1. Marhefka CA, Gao W, Chung K, Kim J, He Y, Yin D, et al. (February 2004). "Design, synthesis, and biological characterization of metabolically stable selective androgen receptor modulators". Journal of Medicinal Chemistry. 47 (4): 993–8. doi:10.1021/jm030336u. PMC 2040239. PMID 14761201.
  2. Jones A, Chen J, Hwang DJ, Miller DD, Dalton JT (January 2009). "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. 150 (1): 385–95. doi:10.1210/en.2008-0674. PMC 2630904. PMID 18772237.
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