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

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2D Structure
Also known as: 117976-90-6, Rebeprazole sodium, Pariet, Aciphex, Rabeprazole sodium salt, Dexrabeprazole sodium
Molecular Formula
C18H20N3NaO3S
Molecular Weight
381.4  g/mol
InChI Key
KRCQSTCYZUOBHN-UHFFFAOYSA-N
FDA UNII
3L36P16U4R

A 4-(3-methoxypropoxy)-3-methylpyridinyl derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]benzimidazol-1-ide
2.1.2 InChI
InChI=1S/C18H20N3O3S.Na/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18;/h3-4,6-9H,5,10-12H2,1-2H3;/q-1;+1
2.1.3 InChI Key
KRCQSTCYZUOBHN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C=CN=C1CS(=O)C2=NC3=CC=CC=C3[N-]2)OCCCOC.[Na+]
2.2 Other Identifiers
2.2.1 UNII
3L36P16U4R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1h-benzimidazole, 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methyl)sulfinyl)-, Sodium Salt

2. 2-((4-(3-methoxypropoxy)-3-methylpyridin-2-yl)methylsulfinyl)-1h-benzimidazole

3. Aciphex

4. Dexrabeprazole

5. E 3810

6. E3810

7. Ly 307640

8. Ly-307640

9. Ly307640

10. Pariet

11. Rabeprazole

12. Sodium, Rabeprazole

2.3.2 Depositor-Supplied Synonyms

1. 117976-90-6

2. Rebeprazole Sodium

3. Pariet

4. Aciphex

5. Rabeprazole Sodium Salt

6. Dexrabeprazole Sodium

7. Rabeprazole (sodium)

8. (s)-rabeprazole Sodium Salt

9. Aciphex Sprinkle

10. Ly307640 Sodium

11. Sodium Rabeprazole

12. Rabeprazole Sodium [usan]

13. Idiazole

14. Rabeprazole Na

15. Chebi:8769

16. 171440-19-0

17. Ly-307640

18. E3810

19. E-3810 Sodium

20. Sodium;2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]benzimidazol-1-ide

21. Ly-307640 Sodium

22. 3l36p16u4r

23. 1h-benzimidazole, 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridinyl)methyl)sulfinyl)-, Sodium Salt

24. 2-(((4-(3-methoxypropoxy)-3-methyl-2-pyridyl)methyl)sulfinyl)benzimidazole Sodium Salt

25. Nsc-759270

26. Dsstox_cid_24205

27. Dsstox_rid_80118

28. Dsstox_gsid_44205

29. 1h-benzimidazole, 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-, Sodium Salt (1:1)

30. Rabicip

31. Pepcia

32. Aciphex Sodium

33. Ly 307640 Sodium

34. Habeprazole Sodium

35. Sodium 2-((4-(3-methoxypropoxy)-3-methylpyridin-2-yl)methylsulfinyl)benzo[d]imidazol-1-ide

36. Sodium 2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)benzimidazol-1-ide

37. Smr000550493

38. Cas-117976-90-6

39. Ncgc00159518-02

40. E 3810

41. Pariete

42. Unii-3l36p16u4r

43. Pariprazole Sodium

44. Dexrabeprazolesodium

45. Rebeprazole Sodium;

46. Aciphex (tn)

47. Pariet (tn)

48. Rebeprazole Sodium Salt

49. Rabeprazole Sodium- Bio-x

50. Mls001165734

51. Mls006010621

52. Schembl140494

53. Rabeprazole Na [vandf]

54. Chembl1200930

55. Dtxsid3044205

56. Rabeprazole Sodium [jan]

57. Hy-b0656a

58. Rabeprazole Sodium (jp17/usp)

59. Ex-a176

60. Hms2093h10

61. Hms2231e04

62. Hms3373b05

63. Rabeprazole Sodium [mart.]

64. Bcp06639

65. Rabeprazole Sodium [usp-rs]

66. Rabeprazole Sodium [who-dd]

67. Tox21_111736

68. Tox21_302317

69. Ac-715

70. Bdbm50247881

71. Mfcd02092688

72. Rabeprazole Sodium Salt [mi]

73. S4665

74. Rabeprazole Sodium, >=98% (hplc)

75. Akos015895734

76. Akos015962116

77. Akos025310160

78. Tox21_111736_1

79. Am81231

80. Ccg-213574

81. Ccg-268423

82. Nsc 759270

83. Rabeprazole Sodium [orange Book]

84. Ncgc00159518-05

85. Ncgc00255838-01

86. Rabeprazole Sodium [ep Monograph]

87. As-13338

88. Br167318

89. Rabeprazole Sodium [usp Monograph]

90. Ft-0631090

91. Ft-0689461

92. R0115

93. C07865

94. D00724

95. F17418

96. 976r906

97. Sr-01000799133

98. J-010726

99. Q-201655

100. Sr-01000799133-2

101. Q27108142

102. [2-[[4-(3-methoxypropoxy)-3-methyl-2-pyridyl]methylsulfinyl]benzimidazol-1-yl]sodium

103. Sodium;2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]-1h-benzimidazole

104. 1h-benzimidazole,2-[[[4-(3-methoxypropoxy)- 3-methyl-2-pyridinyl]methyl]sulfinyl]-,sodium Salt

105. 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1h-benzimidazole, Sodium Salt

106. Sodium 2-(((4-(3-methoxypropoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)benzo[d]imidazol-1-ide

2.4 Create Date
2007-02-09
3 Chemical and Physical Properties
Molecular Weight 381.4 g/mol
Molecular Formula C18H20N3NaO3S
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count8
Exact Mass381.11230696 g/mol
Monoisotopic Mass381.11230696 g/mol
Topological Polar Surface Area81.5 Ų
Heavy Atom Count26
Formal Charge0
Complexity446
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameAciphex
PubMed HealthRabeprazole (By mouth)
Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
Drug LabelThe active ingredient in ACIPHEX Delayed-Release Tablets is rabeprazole sodium, a substituted benzimidazole that inhibits gastric acid secretion. Rabeprazole sodium is known chemically as 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]-methyl]sulfiny...
Active IngredientRabeprazole sodium
Dosage FormTablet, delayed release
Routeoral; Oral
Strength20mg
Market StatusPrescription
CompanyEisai; Eisai Medcl Res

2 of 4  
Drug NameRabeprazole sodium
Drug LabelThe active ingredient in ACIPHEX Delayed-Release Tablets is rabeprazole sodium, a substituted benzimidazole that inhibits gastric acid secretion. Rabeprazole sodium is known chemically as 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]-methyl]sulfiny...
Active IngredientRabeprazole sodium
Dosage FormTablet, delayed release
RouteOral
Strength20mg
Market StatusPrescription
CompanyMylan Pharms; Kremers Urban Dev; Teva Pharms Usa; Torrent Pharms; Lupin; Dr Reddys Labs

3 of 4  
Drug NameAciphex
PubMed HealthRabeprazole (By mouth)
Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
Drug LabelThe active ingredient in ACIPHEX Delayed-Release Tablets is rabeprazole sodium, a substituted benzimidazole that inhibits gastric acid secretion. Rabeprazole sodium is known chemically as 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]-methyl]sulfiny...
Active IngredientRabeprazole sodium
Dosage FormTablet, delayed release
Routeoral; Oral
Strength20mg
Market StatusPrescription
CompanyEisai; Eisai Medcl Res

4 of 4  
Drug NameRabeprazole sodium
Drug LabelThe active ingredient in ACIPHEX Delayed-Release Tablets is rabeprazole sodium, a substituted benzimidazole that inhibits gastric acid secretion. Rabeprazole sodium is known chemically as 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]-methyl]sulfiny...
Active IngredientRabeprazole sodium
Dosage FormTablet, delayed release
RouteOral
Strength20mg
Market StatusPrescription
CompanyMylan Pharms; Kremers Urban Dev; Teva Pharms Usa; Torrent Pharms; Lupin; Dr Reddys Labs

4.2 Drug Indication

Treatment of duodenal ulcer, Treatment of gastric ulcer, Treatment of gastro-oesophageal reflux disease, Treatment of Helicobacter pylori in patients with peptic ulcer disease, Treatment of Zollinger-Ellison syndrome


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


Proton Pump Inhibitors

Compounds that inhibit H(+)-K(+)-EXCHANGING ATPASE. They are used as ANTI-ULCER AGENTS and sometimes in place of HISTAMINE H2 ANTAGONISTS for GASTROESOPHAGEAL REFLUX. (See all compounds classified as Proton Pump Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Proton Pump Inhibitors [MoA]; Proton Pump Inhibitor [EPC]
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