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    Chemistry

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    Also known as: 13209-41-1, Vamorolone [usan], Vbp-15 free alcohol, 17,21-dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione, 16alpha-methyl-9,11-dehydro prednisolone, 8xp29xmb43
    Molecular Formula
    C22H28O4
    Molecular Weight
    356.5  g/mol
    InChI Key
    ZYTXTXAMMDTYDQ-DGEXFFLYSA-N
    FDA UNII
    8XP29XMB43
    Vamorolone
    Vamorolone is under investigation in clinical trial NCT03439670 (A Study to Assess the Efficacy and Safety of Vamorolone in Boys With Duchenne Muscular Dystrophy (DMD)).
    1 2D Structure

    Vamorolone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one
    2.1.2 InChI
    InChI=1S/C22H28O4/c1-13-10-18-16-5-4-14-11-15(24)6-8-20(14,2)17(16)7-9-21(18,3)22(13,26)19(25)12-23/h6-8,11,13,16,18,23,26H,4-5,9-10,12H2,1-3H3/t13-,16-,18+,20+,21+,22+/m1/s1
    2.1.3 InChI Key
    ZYTXTXAMMDTYDQ-DGEXFFLYSA-N
    2.1.4 Canonical SMILES
    CC1CC2C3CCC4=CC(=O)C=CC4(C3=CCC2(C1(C(=O)CO)O)C)C
    2.1.5 Isomeric SMILES
    C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4(C3=CC[C@@]2([C@]1(C(=O)CO)O)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    8XP29XMB43
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Vbp15 Compound

    2.3.2 Depositor-Supplied Synonyms

    1. 13209-41-1

    2. Vamorolone [usan]

    3. Vbp-15 Free Alcohol

    4. 17,21-dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione

    5. 16alpha-methyl-9,11-dehydro Prednisolone

    6. 8xp29xmb43

    7. (8s,10s,13s,14s,16r,17r)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6h-cyclopenta[a]phenanthren-3-one

    8. Chembl2348780

    9. Vbp15

    10. (8s,10s,13s,14s,16r,17r)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthren-3-one

    11. Unii-8xp29xmb43

    12. Vbp 15

    13. Einecs 236-177-8

    14. 16

    15. A-methyl-9,11-dehydro Prednisolone

    16. Vamorolone [inn]

    17. Vamorolone (usan/inn)

    18. Vamorolone [who-dd]

    19. Vbp15vbp15

    20. Schembl143459

    21. Gtpl9247

    22. Amy7535

    23. Dtxsid60927527

    24. Bdbm50432396

    25. Zinc33650317

    26. Db15114

    27. Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16-methyl-, (16.alpha.)-

    28. Hy-109017

    29. Cs-0030515

    30. Dexamethasone Impurity E [ep Impurity]

    31. D11000

    32. 16.alpha.-methyl-9,11-dehydroprednisolone

    33. J-006120

    34. Q27089127

    35. 17,21-dihydroxy-16.alpha.-methylpregna-1,4,9(11)-triene- 3,20-dione

    36. 17.alpha.,21-dihydroxy-16.alpha.-methylpregna-1,4,9(11)-triene-3,20-dione

    37. Delta-1,4,9(11)-pregnatriene-17-alpha,21-dihydroxy-16-alpha-methyl-3,20-dione

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 356.5 g/mol
    Molecular Formula C22H28O4
    XLogP32.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass356.19875937 g/mol
    Monoisotopic Mass356.19875937 g/mol
    Topological Polar Surface Area74.6 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity775
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    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

    Treatment of Duchenne muscular dystrophy

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