Toripristone

Toripristone
Clinical data
Other names	RU-40555; 17β-Hydroxy-11β-[4-[methyl(1-methylethyl)amino]phenyl]-17α-(1-propyn-1-yl)estra-4,9-dien-3-one
Identifiers
	IUPAC name (8S,11R,13S,14S,17S)-17-Hydroxy-13-methyl-11-[4-[methyl(propan-2-yl)amino]phenyl]-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one;
CAS Number	91935-26-1;
PubChem CID	3086344;
ChemSpider	2342997;
UNII	711D76P884;
ChEMBL	ChEMBL2105533;
CompTox Dashboard (EPA)	DTXSID50238795 ;
Chemical and physical data
Formula	C31H39NO2
Molar mass	457.658 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC#C[C@@]1(CC[C@@H]2[C@@]1(C[C@@H](C3=C4CCC(=O)C=C4CC[C@@H]23)C5=CC=C(C=C5)N(C)C(C)C)C)O;
	InChI InChI=1S/C31H39NO2/c1-6-16-31(34)17-15-28-26-13-9-22-18-24(33)12-14-25(22)29(26)27(19-30(28,31)4)21-7-10-23(11-8-21)32(5)20(2)3/h7-8,10-11,18,20,26-28,34H,9,12-15,17,19H2,1-5H3/t26-,27+,28-,30-,31-/m0/s1; Key:LOIYXTZQBQVHSF-PABOLRIOSA-N;

Toripristone (INN; developmental code name RU-40555) is a synthetic, steroidal antiglucocorticoid as well as antiprogestogen which was never marketed.^[1]^[2] It is reported as a potent and highly selective antagonist of the glucocorticoid receptor (GR) (K_i = 2.4 nM),^[3]^[4] though it also acts as an antagonist of the progesterone receptor (PR).^[5]^[6] The pharmacological profile of toripristone is said to be very similar to that of mifepristone, except that toripristone does not bind to orosomucoid (α1-acid glycoprotein).^[5] The drug has been used to study the hypothalamic-pituitary-adrenal axis and has been used as a radiotracer for the GR.^[4]^[3] Its INN was given in 1990.^[2]

References