Acetoxolutamide - Misplaced Pages

Chemical compound

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Pharmaceutical compound

Acetoxolutamide
Clinical data

Drug class	Nonsteroidal androgen; Selective androgen receptor modulator
Identifiers
IUPAC name (2R)-3-(4-acetamidophenoxy)-2-hydroxy-2-methyl-N-propanamide
CAS Number	885324-25-4
PubChem CID	10181786
ChemSpider	8357288
ChEMBL	ChEMBL511130
CompTox Dashboard (EPA)	DTXSID10436497
Chemical and physical data
Formula	C₁₉H₁₈F₃N₃O₆
Molar mass	441.363 g·mol
3D model (JSmol)	Interactive image
SMILES CC(=O)NC1=CC=C(C=C1)OC(C)(C(=O)NC2=CC(=C(C=C2)(=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).

References

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

ARTooltip Androgen receptor

Agonists

17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
5α-Dihydronormethandrone

5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
5α-Dihydronorethisterone

SARMsTooltip Selective androgen receptor modulator

Antagonists

Agonists	Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

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