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    Ulipristal Acetate

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    2D Structure
    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

    2D Structure

    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