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    CAS 734-32-7

    BUILDING BLOCK

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Estr-4-ene-3,17-dione, 19-norandrost-4-ene-3,17-dione, 734-32-7, 19-nor-4-androstene-3,17-dione, Nordione, Delta4-estrene-3,17-dione
    Molecular Formula
    C18H24O2
    Molecular Weight
    272.4  g/mol
    InChI Key
    JRIZOGLBRPZBLQ-QXUSFIETSA-N
    FDA UNII
    U90987PVU5
    19-Norandrostenedione refers to two steroid isomers that were once marketed as dietary supplements and mainly used by body builders. After 2005, 19-Norandrostenedione was regulated in the United States as a schedule III controlled substance, as well as banned from use in competitive sports by the World Anti-Doping Agency. In the body 19-norandrostenedione is rapidly metabolized into [nandrolone], also known as nortestosterone.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8R,9S,10R,13S,14S)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione
    2.1.2 InChI
    InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-16H,2-9H2,1H3/t13-,14+,15+,16-,18-/m0/s1
    2.1.3 InChI Key
    JRIZOGLBRPZBLQ-QXUSFIETSA-N
    2.1.4 Canonical SMILES
    CC12CCC3C(C1CCC2=O)CCC4=CC(=O)CCC34
    2.1.5 Isomeric SMILES
    C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=O)CC[C@H]34
    2.2 Other Identifiers
    2.2.1 UNII
    U90987PVU5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 19-nor-4-androstene-3,17-dione

    2. 19-nor-a-dione

    3. 19-norandrost-4-ene-3,17-dione

    2.3.2 Depositor-Supplied Synonyms

    1. Estr-4-ene-3,17-dione

    2. 19-norandrost-4-ene-3,17-dione

    3. 734-32-7

    4. 19-nor-4-androstene-3,17-dione

    5. Nordione

    6. Delta4-estrene-3,17-dione

    7. Norandrostenedione

    8. Delta,4-estrene-3,17-dione

    9. 19-nor-4-androstenedione

    10. (+)-19-norandrost-4-ene-3,17-dione

    11. .delta.4-estrene-3,17-dione

    12. U90987pvu5

    13. Nsc-12164

    14. (8r,9s,10r,13s,14s)-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

    15. Unii-u90987pvu5

    16. (+)-estr-4-ene-3,17-dione

    17. 3,17-dioxo-19-norandrost-4-ene

    18. Einecs 211-995-8

    19. Nsc 12164

    20. D-19-norandrost-4-ene-3,17-dione

    21. 4-oestrendione

    22. 4-norendione

    23. 4-norendion

    24. Estra4-ene-3,17-dione

    25. Estra-4-ene-3,17-dione

    26. Schembl868884

    27. Chebi:34187

    28. 4-oestren-3,17-dione

    29. Dtxsid50862392

    30. 19-norandrost-4-en-3,17-dione

    31. Nsc12164

    32. Zinc4428372

    33. Akos015896166

    34. Db01434

    35. 19-nor-androstene-4-ene-3,17-dione

    36. Estra-4-en-3,17-dione(19-nor Ad)

    37. 19-nor-4-androstene-3,17-dion

    38. Norethisterone Impurity B [ep Impurity]

    39. (+)-19-norandrost-4-en-3,17-dione

    40. 734n327

    41. Norethindrone Related Compound B [usp-rs]

    42. Q-102802

    43. Q4557695

    44. Norandrostenedione (19-norandrost-4-ene-3,17-dione)

    45. Norethisterone Acetate Impurity J [ep Impurity]

    46. 19-norandrost-4-ene-3,17-dione 100 Microg/ml In Methanol

    47. 19-norandrost-4-en-3,17-dione (8.beta.,9.alpha.,10.beta.)

    48. 19-norandrost-4-ene-3,17-dione 100 Microg/ml In Acetonitrile

    49. Norandrostenedione (19-norandrost-4-ene-3,17-dione) 1.0 Mg/ml In Acetonitrile

    50. (3as,3br,9ar,9bs,11as)-11a-methyl-1h,2h,3h,3ah,3bh,4h,5h,7h,8h,9h,9ah,9bh,10h,11h,11ah-cyclopenta[a]phenanthrene-1,7-dione

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 272.4 g/mol
    Molecular Formula C18H24O2
    XLogP32.5
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count0
    Exact Mass272.177630004 g/mol
    Monoisotopic Mass272.177630004 g/mol
    Topological Polar Surface Area34.1 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity504
    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

    The claim that supplemental 19-norandrostenedione has anabolic effects is unsubstantiated.

    5 Pharmacology and Biochemistry
    5.1 Absorption, Distribution and Excretion

    Absorption

    Absorption appears variable, but some absorption does occur.

    5.2 Metabolism/Metabolites

    Specific metabolites of 19-nor-5-androstene-3, 17-dione are 19-nordehydroandrosterone and 19-nordehydroepiandrosterone.

    5.3 Mechanism of Action

    19-Norandrostenedione may be metabolized to 19-nortestosterone in both men and women. 19-Norandrostenedione, also known as nandrolone, is the basic substance of some very popular injectable anabolic steroids, however 19-norandrostenedione is not metabolized to testosterone. Whether or not increases in 19-nortestosterone levels would be sustained long enough by taking 19-norandrostenedione to show an increase in nitrogen retention and muscle strength and mass is unknown. 19-Norandrostenedione has also been shown to bind to androgen receptors with high selectivity. Transactivation of androgen receptor dependent reporter gene expression was 10 times lower than that produced by dihydrotestosterone. [1]