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    CAS-537-55-3

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    PharmaCompass
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    2D Structure
    Also known as: 537-55-3, Ac-tyr-oh, N-acetyl-tyrosine, Acetyl tyrosine, Acetyl-l-tyrosine, L-tyrosine, n-acetyl-
    Molecular Formula
    C11H13NO4
    Molecular Weight
    223.22  g/mol
    InChI Key
    CAHKINHBCWCHCF-JTQLQIEISA-N
    FDA UNII
    DA8G610ZO5
    N-acetyltyrosine, also referred to as N-acetyl-L-tyrosine, is used in place of as a tyrosine precursor. [DB00135] is a non-essential amino acid with a polar side group. N-acetyltyrosine is administered as parenteral nutrition or intravenous infusion due to its enhanced solubility compared to tyrosine. It is typically administered as a source of nutritional support where oral nutrition is inadequate or cannot be tolerated.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid
    2.1.2 InChI
    InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1
    2.1.3 InChI Key
    CAHKINHBCWCHCF-JTQLQIEISA-N
    2.1.4 Canonical SMILES
    CC(=O)NC(CC1=CC=C(C=C1)O)C(=O)O
    2.1.5 Isomeric SMILES
    CC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    DA8G610ZO5
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Acetyl-l-tyrosine

    2. N-acetyltyrosine

    3. N-acetyltyrosine, (d)-isomer

    4. N-acetyltyrosine, (dl)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 537-55-3

    2. Ac-tyr-oh

    3. N-acetyl-tyrosine

    4. Acetyl Tyrosine

    5. Acetyl-l-tyrosine

    6. L-tyrosine, N-acetyl-

    7. L-n-acetyltyrosine

    8. N-acetyltyrosin

    9. Melanowhite-a

    10. (2s)-2-acetamido-3-(4-hydroxyphenyl)propanoic Acid

    11. Tyrosine, N-acetyl-

    12. Chembl65543

    13. Da8g610zo5

    14. Chebi:21563

    15. (s)-2-acetamido-3-(4-hydroxyphenyl)propanoic Acid

    16. (2s)-2-acetylamino-3-(4-hydroxyphenyl)propanoic Acid

    17. N-acetyltyrosine (n-acetyl-l-tyrosine)

    18. Ncgc00159393-02

    19. Ncgc00159393-03

    20. Dsstox_cid_26045

    21. Dsstox_rid_81305

    22. Dsstox_gsid_46045

    23. (+)-(2s)-2-(acetylamino)-3-(4-hydroxyphenyl)propanoic Acid

    24. Mfcd00037190

    25. Cas-537-55-3

    26. N-aceyl-l-tyrosine

    27. L-tyrosine, Acetyl-

    28. Tyrosine, N-acetyl-, L-

    29. N-acetyltyrosine (van)

    30. Unii-da8g610zo5

    31. Nsc-10853

    32. N-acetyl Tyrosine

    33. Einecs 208-671-3

    34. Nsc 10853

    35. L-n-acetyl-tyrosine

    36. Tanogen Hb

    37. Tyr-excel

    38. Acetyl L-tyrosine

    39. N-acetyl-l-tyrosine,(s)

    40. L-tyrosine, N-acetyl

    41. Schembl321220

    42. Acetyl Tyrosine [inci]

    43. (2s)-2-(acetylamino)-3-(4-hydroxyphenyl)propanoic Acid

    44. Dtxsid7046045

    45. N-acetyltyrosin [who-dd]

    46. Zinc156395

    47. Tox21_111630

    48. Ac7826

    49. Bdbm50043802

    50. S6316

    51. Akos010396311

    52. Akos015841008

    53. N-acetyl-l-tyrosine [usp-rs]

    54. N-acetyl-l-tyrosine, >99% (tlc)

    55. Tox21_111630_1

    56. Am82306

    57. Cs-w013098

    58. Db11102

    59. Hy-w012382

    60. N-acetyltyrosine [ep Monograph]

    61. Ac-13390

    62. Ds-15166

    63. (2s)-2-acetylamino-3-(4-hydroxyphenyl)propanoate

    64. (s)-2-acetamido-3-(4-hydroxyphenyl)propanoicacid

    65. 537a553

    66. A829762

    67. J-300276

    68. N-acetyl-l-tyrosine 100 Microg/ml In Acetonitrile

    69. Q-201443

    70. A53ee723-a216-4295-8abe-c8c9ee26bbfc

    71. Q27109405

    72. (s)-2-acetylamino-3-(4-hydroxy-phenyl)-propionic Acid

    73. 2-(s)-acetylamino-3-(4-hydroxy-phenyl)-propionic Acid

    74. N-acetyltyrosine, European Pharmacopoeia (ep) Reference Standard

    75. N-acetyl-l-tyrosine, United States Pharmacopeia (usp) Reference Standard

    76. N-acetyl-l-tyrosine, Pharmaceutical Secondary Standard; Certified Reference Material

    77. 3nf

    78. N-acetyl-l-tyrosine, Pharmagrade, Ajinomoto, Ep, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

    2.4 Create Date
    2005-07-08
    3 Chemical and Physical Properties
    Molecular Weight 223.22 g/mol
    Molecular Formula C11H13NO4
    XLogP3-0.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass223.08445790 g/mol
    Monoisotopic Mass223.08445790 g/mol
    Topological Polar Surface Area86.6 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity259
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    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

    N-acetyltyrosine is indicated, in combination with several other amino acids and dextrose, as a peripherally administered source of nitrogen for nutritional support in patients with adequate stores of body fat in whom, for short periods, oral administration cannot be tolerated, is undesirable, or inadequate. It is also indicated, with other amino acids, 5-10% dextrose, and fat emulsion, for parenteral nutrition to preserve protein and reduce catabolism in stress conditions where oral administration is inadequate. When administered with other amino acids and concentrated dextrose, it is indicated for central vein infusion to prevent or reverse negative nitrogen balance in patients where the alimentary tract by the oral, gastrostomy, or jejestomy routes cannot or should not be used or in patients in which gastrointestinal absorption of protein is impaired, metabolic requirements for protein are substantially increased, or morbidity and mortality may be reduced by replacing amino acids lost from tissue breakdown

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    N-acetyltyrosine is used as a high solubility precursor to [DB00135] used due to [DB00135]'s poor solubility. It is deacetylated to form [DB00135].

    5.2 Absorption, Distribution and Excretion

    Route of Elimination

    N-acetyltyrosine is eliminated in the urine. The extent of urinary elimination versus utilization in the tissues appears to be related to the rapidity of infusion. When infused slowly in standard doses as in the clinical setting, about 35% is excreted unchanged in the urine. When larger doses are infused rapidly, much higher amounts are excreted reaching values up to 56%. In rat studies it was found that of the drug eliminated in the urine about 74% is present as unchanged N-acetyltyrosine and 23% is present as tyrosine.

    5.3 Mechanism of Action

    Used as a source of [DB00135]. See [DB00135] for more information on its role and pharmacology.