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    Rebamipide

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    2D Structure
    Also known as: 90098-04-7, Proamipide, Mucosta, 111911-87-6, Opc-12759, Rebamipide hydrate
    Molecular Formula
    C19H15ClN2O4
    Molecular Weight
    370.8  g/mol
    InChI Key
    ALLWOAVDORUJLA-UHFFFAOYSA-N
    FDA UNII
    LR583V32ZR
    Rebamipide is a quinolinone derivative with anti-ulcer and anti-inflammatory activities. Rebamipide induces cyclooxygenase 2 (COX2) synthesis which results in an increase in endogenous prostaglandin synthesis in the gastric mucosa. This agent also inhibits H. pylori-induced production of tumor necrosis factor (TNF) alpha and subsequent inflammation of the gastric mucosa. In addition, rebamipide scavenges oxygen-derived free radicals that potentially cause mucosal injury, and stimulates prostaglandin EP4 receptor gene expression followed by mucous secretion, thereby enhancing the gastric mucosal defense.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
    2.1.2 InChI
    InChI=1S/C19H15ClN2O4/c20-13-7-5-11(6-8-13)18(24)22-16(19(25)26)9-12-10-17(23)21-15-4-2-1-3-14(12)15/h1-8,10,16H,9H2,(H,21,23)(H,22,24)(H,25,26)
    2.1.3 InChI Key
    ALLWOAVDORUJLA-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C2C(=C1)C(=CC(=O)N2)CC(C(=O)O)NC(=O)C3=CC=C(C=C3)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    LR583V32ZR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(4-chlorobenzoylamino)-3-(2(1h)-quinolinon-4-yl)propionic Acid

    2. Opc 12759

    3. Opc-12759

    4. Rebamipide, (+)-isomer

    5. Rebamipide, (-)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 90098-04-7

    2. Proamipide

    3. Mucosta

    4. 111911-87-6

    5. Opc-12759

    6. Rebamipide Hydrate

    7. Pramipide

    8. Rebator

    9. 2-(4-chlorobenzoylamino)-3-(1,2-dihydro-2-oxo-4-quinolyl)propionic Acid

    10. 139344-42-6

    11. 2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1h-quinolin-4-yl)propanoic Acid

    12. Nsc-758955

    13. 2-(4-chlorobenzamido)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic Acid

    14. Lr583v32zr

    15. Mfcd00866895

    16. Ncgc00095161-01

    17. 2-(4-chlorobenzamido)-3-[2(1h)-quinolinon-4-yl]propionic Acid

    18. Dsstox_cid_25937

    19. Dsstox_rid_81235

    20. Dsstox_gsid_45937

    21. Rebamipidum

    22. Rebamipide [inn:jan]

    23. 2-[(4-chlorobenzoyl)amino]-3-(2-hydroxyquinolin-4-yl)propanoic Acid

    24. Rebamipidum [inn-latin]

    25. 2-[[(4-chlorophenyl)-oxomethyl]amino]-3-(2-oxo-1h-quinolin-4-yl)propanoic Acid

    26. Opc 12759

    27. Cas-90098-04-7

    28. Ccris 3585

    29. Sr-05000001520

    30. Unii-lr583v32zr

    31. N-[(4-chlorophenyl)carbonyl]-3-(2-oxo-1,2-dihydroquinolin-4-yl)alanine

    32. Dispersered72

    33. 2-[(4-chlorophenyl)carbonylamino]-3-(2-oxidanylidene-1h-quinolin-4-yl)propanoic Acid

    34. Rebamipide-[d4]

    35. Mucosta (tn)

    36. Rebamipide [mi]

    37. Rebamipide [inn]

    38. Rebamipide [jan]

    39. Spectrum2_000039

    40. Spectrum3_001959

    41. Rebamipide (jp17/inn)

    42. (+-)-2-(4-chlorobenzoylamino)-3-(2(1h)-quinolinon-4-yl)propionic Acid

    43. (+-)-1,2-dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo-4-quinolinepropanoic Acid

    44. Rebamipide [who-dd]

    45. Bspbio_003559

    46. Gtpl871

    47. Mls006011883

    48. Schembl221527

    49. Spectrum1505310

    50. Spbio_000137

    51. Rebamipide 111911-87-6

    52. Chembl1697771

    53. Dtxsid8045937

    54. Chebi:93814

    55. Kbio3_002880

    56. Opc-759

    57. Hms1922b20

    58. Hms2090l13

    59. Hms3655l11

    60. Hms3714a15

    61. Pharmakon1600-01505310

    62. Bcp07230

    63. Hy-b0360

    64. Opc12759

    65. Tox21_111460

    66. Bbl011328

    67. Ccg-39619

    68. Nsc758955

    69. S2032

    70. Stk577121

    71. Stl146407

    72. 2-(4-chlorobenzamido)-3-(2-oxo-1,2-dihydro-4-quinolyl)propanoic Acid

    73. Akos005501649

    74. Akos005721106

    75. Tox21_111460_1

    76. Ac-6841

    77. Ac-7588

    78. Db11656

    79. Nsc 758955

    80. 2-(4-chloro-benzoylamino)-3-(2-oxo-1,2-dihydro-quinolin-4-yl)-propionic Acid

    81. 4-quinolinepropanoic Acid, 1,2-dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo-, (+-)-

    82. Ncgc00095161-02

    83. Ncgc00095161-03

    84. Ncgc00095161-04

    85. Ncgc00095161-05

    86. Bc164330

    87. Smr003309276

    88. Sy057250

    89. Vs-02924

    90. Sbi-0207054.p001

    91. Ft-0630971

    92. Ft-0655225

    93. R0085

    94. Sw199113-2

    95. D01121

    96. Ab01275518-01

    97. Ab01275518_02

    98. Ab01275518_03

    99. 911r876

    100. A802443

    101. A843443

    102. A900081

    103. Q-201660

    104. Q7301602

    105. Sr-05000001520-1

    106. Sr-05000001520-2

    107. Sr-05000001520-3

    108. Brd-a15909516-001-02-5

    109. Brd-a15909516-001-03-3

    110. 2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic Acid

    111. 2-(4-chlorobenzoylamino)-3-[2(1h)-quinolinon-4-yl] Propionic Acid

    112. 2-(4-chlorobenzoylamino)-3-[2(1h)-quinolinon-4-yl]propionic Acid

    113. N-[(4-chlorophenyl)carbonyl]-3-(2-hydroxyquinolin-4-yl)alanine

    114. 2-(4-chlorobenzamido)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoicacid

    115. 2-(4-chlorobenzoylamino)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionic Acid

    116. 4-quinolinepropanoicacid,a-[(4-chlorobenzoyl)amino]-1,2-dihydro-2-oxo-

    117. (+/-)-.alpha.-(p-chlorobenzamido)-1,2-dihydro-2-oxo-4-quinolinepropionic Acid

    118. (+/-)-2-(4-chlorobenzoylamino)-3-(2(1h)-quinolinon-4-yl)-propionic Acid

    119. 2-[(4-chlorophenyl)formamido]-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic Acid

    120. 4-quinolinepropanoic Acid, .alpha.-((4-chlorobenzoyl)amino)-1,2-dihydro-2-oxo-

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 370.8 g/mol
    Molecular Formula C19H15ClN2O4
    XLogP32.4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass370.0720347 g/mol
    Monoisotopic Mass370.0720347 g/mol
    Topological Polar Surface Area95.5 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity598
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Antioxidants

    Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

    Anti-Ulcer Agents

    Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

    4.2 ATC Code

    A - Alimentary tract and metabolism

    A02 - Drugs for acid related disorders

    A02B - Drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

    A02BX - Other drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

    A02BX14 - Rebamipide