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(11beta)-17-(Acetyloxy)-11-(4-(dimethylamino)phenyl)-19-norpregna-4,9-diene-3,20-dione
Also known as: 126784-99-4, Cdb-2914, Ella, Ellaone, Cdb 2914, Hrp 2000
Molecular Formula
C30H37NO4
Molecular Weight
475.6  g/mol
InChI Key
OOLLAFOLCSJHRE-ZHAKMVSLSA-N
FDA UNII
YF7V70N02B

Ulipristal Acetate is an orally bioavailable, acetate salt of ulipristal, a selective progesterone receptor modulator with anti-progesterone activity. Ulipristal binds to the progesterone receptor (PR), thereby inhibiting PR-mediated gene expression, and interfering with progesterone activity in the reproductive system. As a result, this agent may suppress the growth of uterine leiomyomatosis. Furthermore, by inhibiting or delaying ovulation and effecting endometrial tissue, ulipristal can be used as an emergency contraception
1 2D Structure

(11beta)-17-(Acetyloxy)-11-(4-(dimethylamino)phenyl)-19-norpregna-4,9-diene-3,20-dione

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(8S,11R,13S,14S,17R)-17-acetyl-11-[4-(dimethylamino)phenyl]-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
2.1.2 InChI
InChI=1S/C30H37NO4/c1-18(32)30(35-19(2)33)15-14-27-25-12-8-21-16-23(34)11-13-24(21)28(25)26(17-29(27,30)3)20-6-9-22(10-7-20)31(4)5/h6-7,9-10,16,25-27H,8,11-15,17H2,1-5H3/t25-,26+,27-,29-,30-/m0/s1
2.1.3 InChI Key
OOLLAFOLCSJHRE-ZHAKMVSLSA-N
2.1.4 Canonical SMILES
CC(=O)C1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)N(C)C)C)OC(=O)C
2.1.5 Isomeric SMILES
CC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H](C3=C4CCC(=O)C=C4CC[C@@H]23)C5=CC=C(C=C5)N(C)C)C)OC(=O)C
2.2 Other Identifiers
2.2.1 UNII
YF7V70N02B
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (11beta)-17-(acetyloxy)-11-(4-(dimethylamino)phenyl)-19-norpregna-4,9-diene-3,20-dione

2. Ella Norpregnadiene

3. Esmya

2.3.2 Depositor-Supplied Synonyms

1. 126784-99-4

2. Cdb-2914

3. Ella

4. Ellaone

5. Cdb 2914

6. Hrp 2000

7. Ulipristal Acetate [usan]

8. Va2914

9. (8s,11r,13s,14s,17r)-17-acetyl-11-(4-(dimethylamino)phenyl)-13-methyl-3-oxo-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl Acetate

10. (11beta)-17-(acetyloxy)-11-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione

11. Yf7v70n02b

12. Chebi:71025

13. 17-acetoxy-11-(4-n,n-dimethylaminophenyl)pregna-4,9-diene-3,20-dione

14. Pgl-4001

15. Va-2914

16. Rti-3021-012

17. Ulipristal (acetate)

18. (11b)-17-(acetyloxy)-11-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione

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

20. (11beta,17alpha)-17-acetyl-11-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17-yl Acetate

21. 17beta-acetyl-11beta-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17alpha-yl Acetate

22. Unii-yf7v70n02b

23. Hrp-2000

24. Ulipristal Acet

25. Mfcd00899035

26. 4oar

27. Ulipristal-acetate

28. Ella Norpregnadiene

29. [(8s,11r,13s,14s,17r)-17-acetyl-11-[4-(dimethylamino)phenyl]-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] Acetate

30. Cbd 2914

31. Ella (tn)

32. Rti 3021-012

33. C17 Epi Ulipristal Acetate

34. Schembl544957

35. Chembl260538

36. Gtpl7460

37. Ulipristal Acetate [mi]

38. Ulipristal Acetate (jan/usan)

39. Ulipristal Acetate [jan]

40. Dtxsid30155294

41. Ta[a]phenanthren-17-yl] Acetate

42. Ulipristal Acetate [vandf]

43. Ulipristal Acetate [mart.]

44. Ulipristal Acetate [who-dd]

45. Zinc3920657

46. Bdbm50375424

47. Ulipristal Acetate, >=98% (hplc)

48. Akos026750526

49. Ccg-269500

50. Cs-1157

51. Ulipristal Acetate [orange Book]

52. Ncgc00378913-02

53. [(8s,11r,13s,14s,17r)-17-acetyl-11-(4-dimethylaminophenyl)-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] Acetate

54. As-73950

55. Bu161520

56. Hy-16508

57. U0102

58. C72119

59. D09687

60. Ab01566874_01

61. 784a994

62. Q975059

63. J-005436

64. Brd-k64381438-001-03-8

65. Z2216208644

66. 5-(hydroxymethyl)-alpha,alpha,alpha,alpha-tetramethyl-1,3-benzenediacetonitrile

67. (10s,11s,14r,15s,17r)-14-acetyl-17-[4-(dimethylamino)phenyl]-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-14-yl Acetate

68. (11.beta.)-17-(acetyloxy)-11-(4-(dimethylamino)phenyl)-19-norpregna-4,9-diene-3,20-dione

69. (11alpha,13alpha,17beta)-17-acetyl-11-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17-yl Acetate

70. (1r,3as,3bs,10r,11as)-1-acetyl-10-[4-(dimethylamino)phenyl]-11a-methyl-7-oxo-1h,2h,3h,3ah,3bh,4h,5h,7h,8h,9h,10h,11h,11ah-cyclopenta[a]phenanthren-1-yl Acetate

71. (8s,11r,13s,14s,17r)-17-acetyl-11-(4-(dimethylamino)phenyl)-13-methyl-3-oxo-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylacetate

72. [(8s,11r,13s,14s,17r)-17-acetyl-11-[4-(dimethylamino)phenyl]-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopen

73. 17.alpha.-acetoxy-11.beta.-(4-dimethylaminophenyl)-19-norpregna-4,9-dien-3,20-dione

74. 19-norpregna-4,9-diene-3,20-dione, 17-(acetyloxy)-11-(4-(dimethylamino)phenyl)-, (11beta)-

75. C17 Isomer Ulipristal Acetate; (10s,11s,14s,15s,17r)-14-acetyl-17-[p-(dimethylamino)phenyl]-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-1,6-dien-14-yl Acetate

76. Cbd 2914; Va 2914; (11b)-17-(acetyloxy)-11-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 475.6 g/mol
Molecular Formula C30H37NO4
XLogP33.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass475.27225866 g/mol
Monoisotopic Mass475.27225866 g/mol
Topological Polar Surface Area63.7 Ų
Heavy Atom Count35
Formal Charge0
Complexity984
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Ulipristal acetate is indicated for one treatment course of pre-operative treatment of moderate to severe symptoms of uterine fibroids in adult women of reproductive age.

Ulipristal acetate is indicated for intermittent treatment of moderate to severe symptoms of uterine fibroids in adult women of reproductive age who are not eligible for surgery.


Emergency contraception within 120 hours (five days) of unprotected sexual intercourse or contraceptive failure.


Contraception


Leiomyoma of uterus


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Contraceptive Agents, Female

Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Female.)


Contraceptive Agents, Hormonal

Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Selective Progesterone Receptor Modulators [MoA]; Progesterone Agonist/Antagonist [EPC]
5.3 ATC Code

G03XB02


G03AD02


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