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ACTIVE PHARMA INGREDIENTS

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Also known as: 198414-30-1, Telapristone [inn], 65703mv349, (8s,11r,13s,14s,17r)-11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(2-methoxyacetyl)-13-methyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-3-one, Unii-65703mv349, Telapristone [who-dd]

Molecular Formula

C₂₉H₃₇NO₄

Molecular Weight

463.6 g/mol

InChI Key

BHERMCLNVOVDPU-DQFOBABISA-N

FDA UNII

65703MV349

Telapristone is an orally available 21-substituted-19-nor-progestin and selective progesterone receptor modulator (SPRM), with potential anti-progesterone and antineoplastic activities. Upon oral administration, telapristone 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. As a result, this agent may suppress ovulation and inhibit proliferation of endometrial tissue. Also, this agent may prevent cell growth and induce apoptosis in estrogen receptor (ER) and PR-positive breast cancer cells through a reduction in progesterone levels, ER downregulation and a suppression of the expression of cyclin-dependent kinases (CDK) 2 and 4, ultimately leading to G1/S cell cycle arrest. Unlike some other SPRMs, this agent does not exert any estrogenic, androgenic, anti-estrogenic, and anti-androgenic activities.

1 2D Structure

Telapristone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8S,11R,13S,14S,17R)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(2-methoxyacetyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

2.1.2 InChI

InChI=1S/C29H37NO4/c1-28-16-24(18-5-8-20(9-6-18)30(2)3)27-22-12-10-21(31)15-19(22)7-11-23(27)25(28)13-14-29(28,33)26(32)17-34-4/h5-6,8-9,15,23-25,33H,7,10-14,16-17H2,1-4H3/t23-,24+,25-,28-,29-/m0/s1

2.1.3 InChI Key

BHERMCLNVOVDPU-DQFOBABISA-N

2.1.4 Canonical SMILES

CC12CC(C3=C4CCC(=O)C=C4CCC3C1CCC2(C(=O)COC)O)C5=CC=C(C=C5)N(C)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(=O)COC)O)C5=CC=C(C=C5)N(C)C

2.2 Other Identifiers

2.2.1 UNII

65703MV349

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 198414-30-1

2. Telapristone [inn]

3. 65703mv349

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

5. Unii-65703mv349

6. Telapristone [who-dd]

7. Schembl2168441

8. Dtxsid00173586

9. 11beta-(4-(dimethylamino)phenyl)-17-hydroxy-21-methoxy-19-norpregna-4,9-diene-3,20-dione

10. 19-norpregna-4,9-diene-3,20-dione, 17-hydroxy-11-(4-(dimethylamino)phenyl)-21-methoxy-, (11beta)-

11. Q27263837

12. (8s,11r,13s,14s,17r)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(2-methoxyacetyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

13. 11.beta.-(4-(dimethylamino)phenyl)-17-hydroxy-21-methoxy-19-norpregna-4,9-diene-3,20-dione

14. 19-norpregna-4,9-diene-3,20-dione, 17-hydroxy-11-(4-(dimethylamino)phenyl)-21-methoxy-, (11.beta.)-

2.4 Create Date

2007-12-05

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₇NO₄
Molecular Weight	463.6 g/mol
XLogP3	2.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	463.27225866 g/mol
Monoisotopic Mass	463.27225866 g/mol
Topological Polar Surface Area	66.8 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	911
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