1262108-37-1

Basic information

• Product Name: (5R,8S,11R,13S,14S,17S)-5',5',13-trimethyl-11-[4-(methylsulfanyl)phenyl]-17-(pentafluoroethyl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxane]-5,17(4H)-diol
• Synonyms: (5R,8S,11R,13S,14S,17S)-5',5',13-trimethyl-11-[4-(methylsulfanyl)phenyl]-17-(pentafluoroethyl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxane]-5,17(4H)-diol
• CAS NO: 1262108-37-1
• Molecular Weight: 616.733
• Mol File: 1262108-37-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (5R,8S,11R,13S,14S,17S)-5',5',13-trimethyl-11-[4-(methylsulfanyl)phenyl]-17-(pentafluoroethyl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxane]-5,17(4H)-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,8S,11R,13S,14S,17S)-5',5',13-trimethyl-11-[4-(methylsulfanyl)phenyl]-17-(pentafluoroethyl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxane]-5,17(4H)-diol(1262108-37-1)
• EPA Substance Registry System: (5R,8S,11R,13S,14S,17S)-5',5',13-trimethyl-11-[4-(methylsulfanyl)phenyl]-17-(pentafluoroethyl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxane]-5,17(4H)-diol(1262108-37-1)

Safety Data

• Hazardous Substances Data: 1262108-37-1(Hazardous Substances Data)

Upstream product

• 91175-93-8 (5′R,8′S,10′R,13′S,14′S)-5,5,13′-trimethyl-1′,2′,6′,7′,8′,12′,13′,14′,15′,16′-decahydro-17′H-spiro[1,3-dioxane-2,3′-[5,10]epoxycyclopenta[a]phenanthren]-17′-one 
• 1026668-61-0 (5′R,8′S,10′R,13′S,14′S,17′S)-5,5,13′-trimethyl-17′-(pentafluoroethyl)-1′,2′,7′,8′,12′,13′,14′,15′,16′,17′-decahydro-6′H-spiro[1,3-dioxane-2,3′-[5,10]epoxycyclopenta[a]phenanthren]-17′-ol 
• 104-95-0 (4-bromophenyl)thioanisole 

Downstream Products

• 1262108-41-7 N-[{4-[(5R,8S,11R,13S,14S,17S)-5,17-dihydroxy-5',5',13-trimethyl-17-(pentafluoroethyl)-1,2,4,5,6,7,8,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxan]-11-yl]phenyl}(methyl)- λ⁴-sulfanylidene]-4-methylbenzenesulfonamide 
• 1262108-42-8 N-[{4-[(5R,8S,11R,13S,14S,17S)-5,17-dihydroxy-5',5',13-trimethyl-17-(pentafluoroethyl)-1,2,4,5,6,7,8,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxan]-11-yl]phenyl}(methyl)oxido-λ⁶-sulfanylidene]-4-methylbenzenesulfonamide 
• 1262108-14-4 (11β,17β)-20,20,21,21,21-pentafluoro-17-hydroxy-11-[4-(methylsulfonyl)phenyl]-19-norpregna-4,9-dien-3-one 
• 1262108-10-0 (11β,17β)-17-Hydroxy-11-{4-[(RS)-methylsulphinyl]phenyl}-17-(pentafluoroethyl)estra-4,9-dien-3-one 
• 1262108-06-4 (11β,17β)-20,20,21,21,21-pentafluoro-17-hydroxy-11-[4-(methylsulfanyl)phenyl]-19-norpregna-4,9-dien-3-one 
• 1262108-18-8 4-methyl-N-[methyl(oxido){4-[(11β,17β)-20,20,21,21,21-pentafluoro-17-hydroxy-3-oxo-19-norpregna-4,9-dien-11-yl]phenyl}-λ⁶-sulfanylidene]benzenesulfonamide 
• 1262108-21-3 (11β,17β)-20,20,21,21,21-pentafluoro-17-hydroxy-11-[4-(S-methylsulfonimidoyl)phenyl]-19-norpregna-4,9-dien-3-one 

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Progesterone plays an important role in the female reproductive system. However, there is also evidence that gynecologic disorders/diseases such as uterine fibroids and endometriosis are progesterone-dependent. Steroidal and non-steroidal selective progesterone receptor modulators (SPRMs) have shown potential for the treatment of such diseases. Steroidal SPRMs, including mifepristone and ulipristal acetate, have proven effective in clinical trials. However, several steroidal SPRMs containing a dimethylamino substituent have been associated with elevated liver enzymes in patients. An earlier drug discovery program identified lonaprisan as a highly selective SPRM that did not show drug-related change in liver enzyme activity. Building on data obtained from that work, here we describe the research program that culminated in the discovery of a novel steroidal SPRM, vilaprisan, which combines an extremely high potency with very favorable drug metabolism and pharmacokinetic properties. Vilaprisan has entered clinical development and is currently undergoing phase 3 clinical trials.