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    Anecortave Acetate

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
    $ API Ref.Price (USD/KG) : 155Xls

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    2D Structure
    Also known as: 7753-60-8, Retaane, Al 3789, Al-3789, Anecortave acetate [usan], Nsc 15475
    Molecular Formula
    C23H30O5
    Molecular Weight
    386.5  g/mol
    InChI Key
    YUWPMEXLKGOSBF-GACAOOTBSA-N
    FDA UNII
    Y0PC411K4T
    Anecortave acetate (Retaane) is an analog of cortisol acetate; among the modifications to the steroid are the removal of the 11 hydroxyl OH group and an addition of a 21-acetate group. As a result of these modifications, anecortave acetate lacks the typical antiinflammatory and immunosuppressive properties of glucocorticoids.Alcon Inc. is developing and marketing Retaane.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-[(8S,10S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
    2.1.2 InChI
    InChI=1S/C23H30O5/c1-14(24)28-13-20(26)23(27)11-8-19-17-5-4-15-12-16(25)6-9-21(15,2)18(17)7-10-22(19,23)3/h7,12,17,19,27H,4-6,8-11,13H2,1-3H3/t17-,19+,21+,22+,23+/m1/s1
    2.1.3 InChI Key
    YUWPMEXLKGOSBF-GACAOOTBSA-N
    2.1.4 Canonical SMILES
    CC(=O)OCC(=O)C1(CCC2C1(CC=C3C2CCC4=CC(=O)CCC43C)C)O
    2.1.5 Isomeric SMILES
    CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)CC[C@@]43C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    Y0PC411K4T
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4,9(11)-pregnadien-17alpha,21-diol-3,20-dione-21-acetate

    2.3.2 Depositor-Supplied Synonyms

    1. 7753-60-8

    2. Retaane

    3. Al 3789

    4. Al-3789

    5. Anecortave Acetate [usan]

    6. Nsc 15475

    7. Nsc 24345

    8. Anecortave [inn]

    9. Nsc-15475

    10. Nsc-24345

    11. 17,21-dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate

    12. Y0pc411k4t

    13. 21-(acetyloxy)-17-hydroxypregna-4,9(11)-diene-3,20-dione

    14. [2-[(8s,10s,13s,14s,17r)-17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Acetate

    15. 17-hydroxy-3,20-dioxopregna-4,9(11)-dien-21-yl Acetate

    16. Anecortave Acetate (200 Mg)f0e2980.997mg/mg(ai)

    17. Retaane Suspension

    18. Unii-y0pc411k4t

    19. Anecortave-acetate

    20. Ncgc00181018-01

    21. Einecs 231-812-5

    22. Anecortave [mart.]

    23. Dsstox_cid_26805

    24. Dsstox_rid_81919

    25. Dsstox_gsid_46805

    26. Schembl94110

    27. 17-hydroxy-3,20-dioxopregna-4,9(11)-dien-21-yl Acetate #

    28. Anecortave Acetate [mi]

    29. Anecortave Acetate (jan/usan)

    30. Anecortave Acetate [jan]

    31. Chembl2106613

    32. Dtxsid5046805

    33. Chebi:31215

    34. Ex-a5253

    35. Nsc15475

    36. Nsc24345

    37. Zinc3931050

    38. Tox21_112668

    39. 17-alpha,21-dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate

    40. Akos015917580

    41. Db05288

    42. Cas-7753-60-8

    43. Hy-116868

    44. Cs-0066714

    45. D01733

    46. Q4761567

    47. Hydrocortisone Acetate Impurity E [ep Impurity]

    48. 21-acetoxy-17-hydroxy-4,9(11)-pregnadiene-3,20-dione

    49. 17alpha-hydroxy-21-acetoxypregna-4,9(11)-diene-3,20-dione

    50. 4,9(11)-pregnadien-17alpha,21-diol-3,20-dione-21-acetate

    51. Pregn-4,9(11)-dien-17,21-diol-3,20-dione, Acetate(ester)

    52. 17alpha-hydroxy-21 -acetoxy-pregna-4,9(11)-diene-3,20-dione

    53. Pregna-4,9(11)-diene-3,20-dione, 21-(acetyloxy)-17-hydroxy-

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 386.5 g/mol
    Molecular Formula C23H30O5
    XLogP32.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass386.20932405 g/mol
    Monoisotopic Mass386.20932405 g/mol
    Topological Polar Surface Area80.7 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity808
    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

    Investigated for use/treatment in glaucoma and macular degeneration.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    Anecortave acetate functions as an antiangiogenic agent, inhibiting blood vessel growth by decreasing extracellular protease expression and inhibiting endothelial cell migration. Its angiostatic activity does not seem to be mediated through any of the commonly known pharmacological receptors. (Ophthalmology 2004;111:2316-7) RETAANE blocks signals from multiple growth factors because it acts downstream and independent of the initiating angiogenic stimuli and inhibits angiogenesis subsequent to the angiogenic stimulation.