Vilaprisan

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Also known as: 1262108-14-4, Vilaprisan [inn], Bay1002670, In59k53gi9, Bay-1002670, (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

Molecular Formula

C₂₇H₂₉F₅O₄S

Molecular Weight

544.6 g/mol

InChI Key

JUFWQQVHQFDUOD-ANRPBIDPSA-N

FDA UNII

IN59K53GI9

Vilaprisan is an orally available progestin and selective progesterone receptor modulator (SPRM), with potential anti-progesterone and antineoplastic activities. Upon oral administration, vilaprisan competitively binds to the progesterone receptor (PR) in progesterone-responsive tissue and inhibits PR-mediated gene expression. This interferes with progesterone activity in the reproductive system and may inhibit PR-mediated proliferative effects in cells overexpressing PRs. As a result, this agent may suppress ovulation and inhibit proliferation of endometrial tissue or uterine fibroid formation.

1 2D Structure

Vilaprisan

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

JUFWQQVHQFDUOD-ANRPBIDPSA-N

2.1.4 Canonical SMILES

CC12CC(C3=C4CCC(=O)C=C4CCC3C1CCC2(C(C(F)(F)F)(F)F)O)C5=CC=C(C=C5)S(=O)(=O)C

2.1.5 Isomeric 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

2.2 Other Identifiers

2.2.1 UNII

IN59K53GI9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bay 1002670

2.3.2 Depositor-Supplied Synonyms

1. 1262108-14-4

2. Vilaprisan [inn]

3. Bay1002670

4. In59k53gi9

5. Bay-1002670

6. (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

7. 19-norpregna-4,9-dien-3-one, 20,20,21,21,21-pentafluoro-17-hydroxy-11-(4-(methylsulfonyl)phenyl)-, (11beta,17alpha)-

8. 19-norpregna-4,9-dien-3-one, 20,20,21,21,21-pentafluoro-17-hydroxy-11-[4-(methylsulfonyl)phenyl]-, (11beta,17alpha)-

9. Unii-in59k53gi9

10. Bay 1002670

11. Vilaprisan [jan]

12. Vilaprisan [usan:inn]

13. Vilaprisan [usan]

14. Vilaprisan [who-dd]

15. Vilaprisan (jan/usan/inn)

16. Schembl2121854

17. Chembl3989936

18. Dtxsid201110777

19. Bcp24069

20. Db11971

21. 20,20,21,21,21-pentafluoro-17-hydroxy-11beta-(4-(methanesulfonyl)phenyl)-19-nor-17alpha-pregna-4,9-dien-3-one

22. Ac-30930

23. D11181

24. Q27280805

25. (8s,11r,13s,14s,17r)-17-hydroxy-13-methyl-11-(4-(methylsulfonyl)phenyl)-17-(perfluoroethyl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-3-one

26. 19-norpregna-4,9-dien-3-one, 20,20,21,21,21-pentafluoro-17-hydroxy-11-(4-(methylsulfonyl)phenyl)-, (11.beta.,17.alpha.)-

27. 20,20,21,21,21-pentafluoro-17-hydroxy-11.beta.-(4-(methanesulfonyl)phenyl)-19-nor-17.alpha.-pregna-4,9-dien-3-one

28. Bay1002670; Bay-1002670; Bay 1002670; Bay-10-02670; Bay10-02670; Bay 10-02670

2.4 Create Date

2011-03-14

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₉F₅O₄S
Molecular Weight	544.6 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	544.17067139 g/mol
Monoisotopic Mass	544.17067139 g/mol
Topological Polar Surface Area	79.8 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	1140
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1