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11 Beta-(4-dimethylaminophenyl)-17 Alpha-hydroxy-17 Beta-(3-hydroxypropyl)-13 Alpha-methyl-4,9-gonadien-3-one

11 beta-(4-dimethylaminophenyl)-17 alpha-hydroxy-17 beta-(3-hydroxypropyl)-13 alpha-methyl-4,9-gonadien-3-one

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11 beta-(4-dimethylaminophenyl)-17 alpha-hydroxy-17 beta-(3-hydroxypropyl)-13 alpha-methyl-4,9-gonadien-3-one

Also known as: 96346-61-1, Onapristone [inn], Zk-98299, Zk-299, Zk98299, H6h7g23o3n

Molecular Formula

C₂₉H₃₉NO₃

Molecular Weight

449.6 g/mol

InChI Key

IEXUMDBQLIVNHZ-YOUGDJEHSA-N

FDA UNII

H6H7G23O3N

Onapristone is an orally bioavailable progesterone receptor (PR) antagonist, with potential antineoplastic activity. Upon oral administration, onapristone binds to the PR and inhibits both PR activation and the associated expression of PR-responsive genes. This may inhibit PR-mediated proliferative effects in cancer cells overexpressing PR. In addition, onapristone may downregulate cancer stem cell mobilization and block immune evasion. PR is expressed on certain cancer cell types and plays a key role in tumor cell proliferation and survival.

1 2D Structure

11 beta-(4-dimethylaminophenyl)-17 alpha-hydroxy-17 beta-(3-hydroxypropyl)-13 alpha-methyl-4,9-gonadien-3-one

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C29H39NO3/c1-28-18-25(19-5-8-21(9-6-19)30(2)3)27-23-12-10-22(32)17-20(23)7-11-24(27)26(28)13-15-29(28,33)14-4-16-31/h5-6,8-9,17,24-26,31,33H,4,7,10-16,18H2,1-3H3/t24-,25+,26-,28+,29+/m0/s1

2.1.3 InChI Key

IEXUMDBQLIVNHZ-YOUGDJEHSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

H6H7G23O3N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 11 Beta-(4-dimethylaminophenyl)-17 Alpha-hydroxy-17 Beta-(3-hydroxypropyl)-13 Alpha-methyl-4,9-gonadien-3-one

2. Zk 299

3. Zk 98.299

4. Zk 98299

5. Zk-299

6. Zk-98299

2.3.2 Depositor-Supplied Synonyms

1. 96346-61-1

2. Onapristone [inn]

3. Zk-98299

4. Zk-299

5. Zk98299

6. H6h7g23o3n

7. Zk299

8. Onapristone (inn)

9. Onapristonum [latin]

10. Onapristona [spanish]

11. Onapristona

12. Onapristonum

13. Zk 299

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

15. Ccris 6530

16. Zk 98299

17. Unii-h6h7g23o3n

18. Zk 98.299

19. Xe 299

20. Onapristone [mi]

21. Schembl8740

22. Onapristone [who-dd]

23. Gtpl2882

24. Tetrafluoroethylene Dimethylamine

25. Chembl1908373

26. Dtxsid90242210

27. Ivv-1001

28. Zinc3831947

29. Bdbm50366558

30. Nsc792824

31. Akos025311420

32. Db12637

33. Nsc-792824

34. (8s,11r,13r,14s,17s)-11-(4-dimethylaminophenyl)-17-hydroxy-17-(3-hydroxypropyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

35. 11beta-(p-(dimethylamino)phenyl)-17alpha-hydroxy-17-(3-hydroxypropyl)-13alpha-estra-4,9-dien-3-one

36. Bo161274

37. Estra-4,9-dien-3-one, 11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(3-hydroxypropyl)-, (11-beta,13-alpha,17-alpha)-

38. Hy-106389

39. Cs-0025702

40. D09571

41. Q27088181

42. (8s,11r,13r,14s,17s)-11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(3-hydroxypropyl)-13-methyl-6,7,8,11,12,13,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

43. (8s,11r,13r,14s,17s)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxypropyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

44. 11.beta.-(p-(dimethylamino)phenyl)-17.alpha.-hydroxy-17-(3-hydroxypropyl)-13.alpha.-estra-4,9-dien-3-one

45. Estra-4,9-dien-3-one, 11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxypropyl)-, (11.beta.,13.alpha.,17.alpha.)-

46. Estra-4,9-dien-3-one,11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxypropyl)-,(11b,13a,17a)-

2.4 Create Date

2005-12-16

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₉NO₃
Molecular Weight	449.6 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	449.29299411 g/mol
Monoisotopic Mass	449.29299411 g/mol
Topological Polar Surface Area	60.8 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	836
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

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Fertility Agents, Female

Compounds which increase the capacity to conceive in females. (See all compounds classified as Fertility Agents, Female.)

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Hormone Antagonists

Chemical substances which inhibit the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. (See all compounds classified as Hormone Antagonists.)