Acetoxolutamide

Acetoxolutamide is a nonsteroidal androgen and selective androgen receptor modulator (SARM) which was described in 2000 and was never developed or marketed for medical use.[1] It was derived from structural modification of the nonsteroidal antiandrogen bicalutamide and the nonsteroidal SARM acetothiolutamide.[1] Acetoxolutamide shows greatly improved pharmacokinetic properties and anabolic and androgenic potency relative to acetothiolutamide in animals.[1] It is the (2R) enantiomer of andarine (also known as acetamidoxolutamide or androxolutamide).[1]

Acetoxolutamide
Clinical data
Drug classNonsteroidal androgen; Selective androgen receptor modulator
Identifiers
IUPAC name
  • (2R)-3-(4-acetamidophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H18F3N3O6
Molar mass441.363 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)NC1=CC=C(C=C1)OC[C@](C)(C(=O)NC2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)O
InChI
  • InChI=1S/C19H18F3N3O6/c1-11(26)23-12-3-6-14(7-4-12)31-10-18(2,28)17(27)24-13-5-8-16(25(29)30)15(9-13)19(20,21)22/h3-9,28H,10H2,1-2H3,(H,23,26)(H,24,27)/t18-/m1/s1
  • Key:YVXVTLGIDOACBJ-GOSISDBHSA-N

References
  1. Yin D (December 2000). Pharmacology, Pharmacokinetics and Metabolism of Nonsteroidal Androgens (Ph.D. thesis). The University of Tennessee Health Science Center. ProQuest 304669272.



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