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    Bezisterim

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
    Xls

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    2D Structure
    Also known as: He3286, 1001100-69-1, He 3286, Bezisterim, He-3286, Unii-ph8858757i
    Molecular Formula
    C21H30O3
    Molecular Weight
    330.5  g/mol
    InChI Key
    JJKOQZHWYLMASZ-FJWDNACWSA-N
    FDA UNII
    PH8858757I
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3S,7R,8R,9S,10R,13S,14S,17R)-17-ethynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,7,17-triol
    2.1.2 InChI
    InChI=1S/C21H30O3/c1-4-21(24)10-7-16-18-15(6-9-20(16,21)3)19(2)8-5-14(22)11-13(19)12-17(18)23/h1,12,14-18,22-24H,5-11H2,2-3H3/t14-,15-,16-,17-,18+,19-,20-,21-/m0/s1
    2.1.3 InChI Key
    JJKOQZHWYLMASZ-FJWDNACWSA-N
    2.1.4 Canonical SMILES
    CC12CCC(CC1=CC(C3C2CCC4(C3CCC4(C#C)O)C)O)O
    2.1.5 Isomeric SMILES
    C[C@]12CC[C@@H](CC1=C[C@@H]([C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    PH8858757I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 17-ethynyl-5-androstene-3, 7, 17-triol

    2. 17-ethynyl-5-androstene-3,7,17-triol

    3. He-3286

    4. He3286

    2.3.2 Depositor-Supplied Synonyms

    1. He3286

    2. 1001100-69-1

    3. He 3286

    4. Bezisterim

    5. He-3286

    6. Unii-ph8858757i

    7. Pregn-5-en-20-yne-3,7,17-triol, (3beta,7beta,17alpha)-

    8. Ph8858757i

    9. 3beta,7beta,17beta-trihydroxy-17alpha-ethynylandrost-5-ene

    10. (3s,7r,8r,9s,10r,13s,14s,17r)-17-ethynyl-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,7,17-triol

    11. Bezisterim [inn]

    12. 17-ethynyl-5-androstene-3, 7, 17-triol

    13. Schembl512549

    14. Chembl4297284

    15. Dtxsid501267252

    16. Akos040749677

    17. Db05212

    18. Hy-108039

    19. Cs-0027210

    20. Ns00072554

    21. G13918

    22. 17alpha-pregn-5-en-20-yne-3beta,7beta,17-triol

    23. Q27286562

    24. 17.alpha.-ethynyl-5-androstene-3.beta.,7.beta.,17.beta.-triol

    25. Pregn-5-en-20-yne-3,7,17-triol, (3.beta.,7.beta.,17.alpha.)-

    2.4 Create Date
    2007-10-01
    3 Chemical and Physical Properties
    Molecular Weight 330.5 g/mol
    Molecular Formula C21H30O3
    XLogP32.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count1
    Exact Mass g/mol
    Monoisotopic Mass g/mol
    Topological Polar Surface Area60.7
    Heavy Atom Count24
    Formal Charge0
    Complexity630
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    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

    For the treatment of rheumatoid arthritis and type 2 diabetes.

    5 Pharmacology and Biochemistry
    5.1 Absorption, Distribution and Excretion

    Absorption

    Up to 25% oral bioavailability in mice.

    5.2 Mechanism of Action

    Potential mechanisms of action for HE3286 include regulation of NF-kB and increasing the production of regulatory T cells (Treg cells). NF-kB is a well-known transcription factor that controls the production of inflammatory cytokines such as TNF-a and interferon-g. Treg cells are referred to in the scientific literature as the peacekeepers of the body. Their role is to keep the immune system from attacking the body itself. Recent studies of Treg cells indicate that they may play a broader role than simply preventing autoimmune conditions. Manipulation of these cells may offer new treatments for conditions ranging from diabetes and organ rejection to cancer and infectious diseases. In type II diabetes, moderate inhibition of NF-kB improves glucose tolerance. [Press Release - Hollis-Eden Pharmaceuticals]