Lonaprisan

Lonaprisan
Clinical data
Other names	ZK-230211; BAY 86-5044; ZK-PRA; 11β-(4-acetylphenyl)-17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)estra-4,9-dien-3-one
Routes of; administration	Oral
Identifiers
	IUPAC name (8S,11R,13S,14S,17S)-11-(4-acetylphenyl)-17-hydroxy-13-methyl-17-(1,1,2,2,2-pentafluoroethyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one;
CAS Number	211254-73-8;
PubChem CID	6918548;
ChemSpider	5293745;
UNII	F5Z5EL4D26;
KEGG	D10016;
ChEMBL	ChEMBL146032;
CompTox Dashboard (EPA)	DTXSID60893551 ;
ECHA InfoCard	100.190.674
Chemical and physical data
Formula	C28H29F5O3
Molar mass	508.529 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)C1=CC=C(C=C1)[C@H]2C[C@]3([C@@H](CC[C@]3(C(C(F)(F)F)(F)F)O)[C@H]4C2=C5CCC(=O)C=C5CC4)C;
	InChI InChI=1S/C28H29F5O3/c1-15(34)16-3-5-17(6-4-16)22-14-25(2)23(11-12-26(25,36)27(29,30)28(31,32)33)21-9-7-18-13-19(35)8-10-20(18)24(21)22/h3-6,13,21-23,36H,7-12,14H2,1-2H3/t21-,22+,23-,25-,26-/m0/s1; Key:VHZPUDNSVGRVMB-RXDLHWJPSA-N;

Lonaprisan (INN, USAN) (developmental code names ZK-230211, BAY 86-5044, ZK-PRA) is a synthetic, steroidal antiprogestogen which was under development by Bayer HealthCare Pharmaceuticals for the treatment of endometriosis, dysmenorrhea, and breast cancer but was discontinued.^[1]^[2]^[3] It is a potent and highly selective silent antagonist of the progesterone receptor (PR).^[2]^[3]^[4] The drug reached phase II clinical trials prior to its discontinuation.^[1]

References

Clinical data

Other names	ZK-230211; BAY 86-5044; ZK-PRA; 11β-(4-acetylphenyl)-17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)estra-4,9-dien-3-one
Routes of administration	Oral
Identifiers
IUPAC name (8S,11R,13S,14S,17S)-11-(4-acetylphenyl)-17-hydroxy-13-methyl-17-(1,1,2,2,2-pentafluoroethyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
CAS Number	211254-73-8
PubChem CID	6918548
ChemSpider	5293745
UNII	F5Z5EL4D26
KEGG	D10016
ChEMBL	ChEMBL146032
CompTox Dashboard (EPA)	DTXSID60893551
ECHA InfoCard	100.190.674
Chemical and physical data
Formula	C₂₈H₂₉F₅O₃
Molar mass	508.529 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)C1=CC=C(C=C1)[C@H]2C[C@]3([C@@H](CC[C@]3(C(C(F)(F)F)(F)F)O)[C@H]4C2=C5CCC(=O)C=C5CC4)C
InChI InChI=1S/C28H29F5O3/c1-15(34)16-3-5-17(6-4-16)22-14-25(2)23(11-12-26(25,36)27(29,30)28(31,32)33)21-9-7-18-13-19(35)8-10-20(18)24(21)22/h3-6,13,21-23,36H,7-12,14H2,1-2H3/t21-,22+,23-,25-,26-/m0/s1 Key:VHZPUDNSVGRVMB-RXDLHWJPSA-N