Vilaprisan

Vilaprisan
Clinical data
Other names	BAY-1002670; 17β-Hydroxy-11β-[4-(methylsulfonyl)phenyl]-17α-(1,1,2,2,2-pentafluoroethyl)estra-4,9-dien-3-one
Routes of; administration	By mouth
Drug class	Selective progesterone receptor modulator
Identifiers
	IUPAC name (8S,11R,13S,14S,17S)-17-Hydroxy-13-methyl-11-(4-methylsulfonylphenyl)-17-(1,1,2,2,2-pentafluoroethyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one;
CAS Number	1262108-14-4;
PubChem CID	50915138;
ChemSpider	32699892;
UNII	IN59K53GI9;
KEGG	D11181;
CompTox Dashboard (EPA)	DTXSID201110777 ;
Chemical and physical data
Formula	C27H29F5O4S
Molar mass	544.58 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12C[C@@H](C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(C(C(F)(F)F)(F)F)O)C5=CC=C(C=C5)S(=O)(=O)C;
	InChI InChI=1S/C27H29F5O4S/c1-24-14-21(15-3-7-18(8-4-15)37(2,35)36)23-19-10-6-17(33)13-16(19)5-9-20(23)22(24)11-12-25(24,34)26(28,29)27(30,31)32/h3-4,7-8,13,20-22,34H,5-6,9-12,14H2,1-2H3/t20-,21+,22-,24-,25-/m0/s1; Key:JUFWQQVHQFDUOD-ANRPBIDPSA-N;

Vilaprisan (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (developmental code name BAY-1002670) is a synthetic and steroidal selective progesterone receptor modulator (SPRM) which is under development by Bayer HealthCare Pharmaceuticals for the treatment of endometriosis and uterine fibroids.^[1]^[2]^[3] It is a potent and highly selective partial agonist of the progesterone receptor (PR).^[4]^[2]^[3] As of 2017, the drug is in phase II clinical trials for the aforementioned indications.^[1]

References

^ ^a ^b "Vilaprisan - Bayer HealthCare Pharmaceuticals - AdisInsight".
^ ^a ^b Whitaker LH, Williams AR, Critchley HO (2014). "Selective progesterone receptor modulators". Curr. Opin. Obstet. Gynecol. 26 (4): 237–42. doi:10.1097/GCO.0000000000000082. PMID 24950125. S2CID 37474964.
^ ^a ^b Pluchino N, Freschi L, Wenger JM, Streuli I (2016). "Innovations in classical hormonal targets for endometriosis". Expert Rev Clin Pharmacol. 9 (2): 317–27. doi:10.1586/17512433.2016.1129895. PMID 26645363. S2CID 8624056.
^ Schütt B, Kaiser A, Schultze-Mosgau MH, Seitz C, Bell D, Koch M, Rohde B (2016). "Pharmacodynamics and safety of the novel selective progesterone receptor modulator vilaprisan: a double-blind, randomized, placebo-controlled phase 1 trial in healthy women". Hum. Reprod. 31 (8): 1703–12. doi:10.1093/humrep/dew140. PMID 27288475.

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Clinical data

Other names	BAY-1002670; 17β-Hydroxy-11β-[4-(methylsulfonyl)phenyl]-17α-(1,1,2,2,2-pentafluoroethyl)estra-4,9-dien-3-one
Routes of administration	By mouth
Drug class	Selective progesterone receptor modulator
Identifiers
IUPAC name (8S,11R,13S,14S,17S)-17-Hydroxy-13-methyl-11-(4-methylsulfonylphenyl)-17-(1,1,2,2,2-pentafluoroethyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
CAS Number	1262108-14-4
PubChem CID	50915138
ChemSpider	32699892
UNII	IN59K53GI9
KEGG	D11181
CompTox Dashboard (EPA)	DTXSID201110777
Chemical and physical data
Formula	C₂₇H₂₉F₅O₄S
Molar mass	544.58 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@]12C[C@@H](C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(C(C(F)(F)F)(F)F)O)C5=CC=C(C=C5)S(=O)(=O)C
InChI InChI=1S/C27H29F5O4S/c1-24-14-21(15-3-7-18(8-4-15)37(2,35)36)23-19-10-6-17(33)13-16(19)5-9-20(23)22(24)11-12-25(24,34)26(28,29)27(30,31)32/h3-4,7-8,13,20-22,34H,5-6,9-12,14H2,1-2H3/t20-,21+,22-,24-,25-/m0/s1 Key:JUFWQQVHQFDUOD-ANRPBIDPSA-N