Acetothiolutamide

Acetothiolutamide
Clinical data
Other names	Thioacetolutamide
Identifiers
	IUPAC name (2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-acetamidophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide;
CAS Number	216665-38-2;
PubChem CID	10873814;
ChemSpider	9049091;
UNII	SW1TF3RGAH;
ChEMBL	ChEMBL121940;
CompTox Dashboard (EPA)	DTXSID8040806 ;
Chemical and physical data
Formula	C20H18F3N3O3S
Molar mass	437.44 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)NC1=CC=C(C=C1)SCC(C)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O;
	InChI InChI=1S/C20H18F3N3O3S/c1-12(27)25-14-5-7-16(8-6-14)30-11-19(2,29)18(28)26-15-4-3-13(10-24)17(9-15)20(21,22)23/h3-9,29H,11H2,1-2H3,(H,25,27)(H,26,28)/t19-/m0/s1; Key:FEDHYHIWSREKGN-IBGZPJMESA-N;

Acetothiolutamide is a selective androgen receptor modulator (SARM) derived from the nonsteroidal antiandrogen bicalutamide that was described in 2002 and was one of the first SARMs to be discovered and developed.^[1]^[2]^[3]^[4] It is a high-affinity, selective ligand of the androgen receptor (AR) (K_i = 2.1–4.9 nM), where it acts as a full agonist in vitro, and has in vitro potency comparable to that of testosterone.^[2]^[4]^[5] However, in vivo, acetothiolutamide displayed overall negligible androgenic effects, though significant (albeit very low) anabolic effects were observed at high doses.^[2] In addition, notable antiandrogen effects were observed in castrated male rats treated with testosterone propionate.^[2] The discrepancy between the in vitro and in vivo actions of acetothiolutamide was determined to be related to rapid plasma clearance and extensive hepatic metabolism into a variety of metabolites with differing pharmacological activity, including AR partial agonism and antagonism.^[2]^[4]^[6] In accordance with its poor metabolic stability, acetothiolutamide is not orally bioavailable, and shows activity only via injected routes such as subcutaneous and intravenous.^[2]

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