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    N-Acetylcysteine Amide

    DEVELOPMENTS

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    2D Structure
    Also known as: 38520-57-9, (r)-2-acetamido-3-mercaptopropanamide, Acetylcysteine amide, Nac amide, N-acetyl-l-cysteinamide, Naca
    Molecular Formula
    C5H10N2O2S
    Molecular Weight
    162.21  g/mol
    InChI Key
    UJCHIZDEQZMODR-BYPYZUCNSA-N
    FDA UNII
    4N69717RKW
    N-Acetylcysteine Amide is the amide form of N-acetylcysteine (NAC), a synthetic N-acetyl derivative and prodrug of the endogenous amino acid and antioxidant glutathione (GSH) precursor L-cysteine, with potential antioxidant and anti-inflammatory activities. Upon administration, N-acetylcysteine amide (NACA) increases GSH levels. GSH scavenges reactive oxygen species (ROS), reduces oxidative stress and prevents ROS-mediated cell damage and apoptosis. NACA has enhanced lipophilicity and membrane permeability compared with NAC.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R)-2-acetamido-3-sulfanylpropanamide
    2.1.2 InChI
    InChI=1S/C5H10N2O2S/c1-3(8)7-4(2-10)5(6)9/h4,10H,2H2,1H3,(H2,6,9)(H,7,8)/t4-/m0/s1
    2.1.3 InChI Key
    UJCHIZDEQZMODR-BYPYZUCNSA-N
    2.2 Other Identifiers
    2.2.1 UNII
    4N69717RKW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-acetamido-3-mercapto-l-propionamide

    2. N-acetylcysteinamide

    2.3.2 Depositor-Supplied Synonyms

    1. 38520-57-9

    2. (r)-2-acetamido-3-mercaptopropanamide

    3. Acetylcysteine Amide

    4. Nac Amide

    5. N-acetyl-l-cysteinamide

    6. Naca

    7. Acetylcysteinamide

    8. N-acetyl-l-cysteine Amide

    9. N-acetyl Cysteine Amide

    10. N-acetyl-cysteine-amide

    11. N-acetylcysteinamide

    12. Propanamide, 2-(acetylamino)-3-mercapto-, (2r)-

    13. Mfcd01696115

    14. 4n69717rkw

    15. Propanamide, 2-(acetylamino)-3-mercapto-, (r)-

    16. (2r)-2-acetamido-3-sulfanylpropanamide

    17. (2r)-2-(acetylamino)-3-mercaptopropanamide;

    18. Unii-4n69717rkw

    19. N-acetylcysteine Amide [who-dd]

    20. Ac-cys-nh2

    21. (r)- 2-(acetylamino)-3-mercapto-propanamide

    22. N-acetylcysteine Amide;(r)-2-acetamido-3-mercaptopropanamide

    23. Schembl377413

    24. Dtxsid30436398

    25. Chebi:231847

    26. Ujchizdeqzmodr-bypyzucnsa-n

    27. Hms3886b05

    28. S5804

    29. Akos006373417

    30. Db14480

    31. Da-55966

    32. N-acetylcysteine Amide, >=98% (hplc)

    33. Hy-110256

    34. Cs-0033121

    35. Q15408428

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 162.21 g/mol
    Molecular Formula C5H10N2O2S
    XLogP3-0.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area73.2
    Heavy Atom Count10
    Formal Charge0
    Complexity149
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1