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Technical details about Rebamipide, learn more about the structure, uses, toxicity, action, side effects and more

Rebamipide

Synopsis, Chemistry

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Rebamipide
Chemistry
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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 Formula	C₁₉H₁₅ClN₂O₄
Molecular Weight	370.8 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	370.0720347 g/mol
Monoisotopic Mass	370.0720347 g/mol
Topological Polar Surface Area	95.5 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	598
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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

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