Chemistry:Acetoxolutamide

Short description: Chemical compound

Acetoxolutamide

Clinical data
Drug class	Nonsteroidal 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	885324-25-4
PubChem CID	10181786
ChemSpider	8357288
ChEMBL	ChEMBL511130
Chemical and physical data
Formula	C19H18F3N3O6
Molar mass	441.363 g·mol−1
3D model (JSmol)	Interactive image
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

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. It was derived from structural modification of the nonsteroidal antiandrogen bicalutamide and the nonsteroidal SARM acetothiolutamide. Acetoxolutamide shows greatly improved pharmacokinetic properties and anabolic and androgenic potency relative to acetothiolutamide in animals. It is the (2R) enantiomer of andarine (also known as acetamidoxolutamide or androxolutamide).