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Naproxen Sodium
Also known as: 26159-34-2, Naprelan, Anaprox, Naproxen sodium salt, Miranax, (-)-naproxen sodium
Molecular Formula
C14H13NaO3
Molecular Weight
252.24  g/mol
InChI Key
CDBRNDSHEYLDJV-FVGYRXGTSA-M
FDA UNII
9TN87S3A3C

An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout.
1 2D Structure

Naproxen Sodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(2S)-2-(6-methoxynaphthalen-2-yl)propanoate
2.1.2 InChI
InChI=1S/C14H14O3.Na/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10;/h3-9H,1-2H3,(H,15,16);/q;+1/p-1/t9-;/m0./s1
2.1.3 InChI Key
CDBRNDSHEYLDJV-FVGYRXGTSA-M
2.1.4 Canonical SMILES
CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)[O-].[Na+]
2.1.5 Isomeric SMILES
C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)[O-].[Na+]
2.2 Other Identifiers
2.2.1 UNII
9TN87S3A3C
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aleve

2. Anaprox

3. Methoxypropiocin

4. Naprosin

5. Naprosyn

6. Naproxen

7. Naproxenate, Sodium

8. Proxen

9. Sodium Naproxenate

10. Sodium, Naproxen

11. Synflex

2.3.2 Depositor-Supplied Synonyms

1. 26159-34-2

2. Naprelan

3. Anaprox

4. Naproxen Sodium Salt

5. Miranax

6. (-)-naproxen Sodium

7. Aleve

8. Naproxen (sodium)

9. Naprium

10. Naprux

11. Proxen

12. Sodium (s)-2-(6-methoxynaphthalen-2-yl)propanoate

13. Bayh6689

14. Apo-napro-na

15. (s)-naproxen Sodium Salt

16. Sodium Naproxen

17. Rs-3650

18. Naproxen Sodium Anhydrous

19. Mls000069555

20. 9tn87s3a3c

21. Chebi:7477

22. (-)-sodium (s)-6-methoxy-alpha-methyl-2-naphthaleneacetate

23. 2-naphthaleneacetic Acid, 6-methoxy-alpha-methyl-, Sodium Salt, (s)-

24. Bay117031

25. Sodium;(2s)-2-(6-methoxynaphthalen-2-yl)propanoate

26. Bay-117031

27. Ncgc00017097-01

28. Anapran

29. Anaprotab

30. Aprowell

31. Floginex

32. Flogogin

33. Floneks

34. Floxalin

35. Gibinap

36. Gibixen

37. Karoksen

38. Leniartril

39. Monarit

40. Naprodil

41. Naprodol

42. Naprovite

43. Natrioxen

44. Pactens

45. Primeral

46. Smr000058746

47. Sodimax

48. Synflex

49. Flogen

50. Kapnax

51. Opraks

52. Tandax

53. (s)-6-methoxy-alpha-methyl-2-naphthaleneacetic Acid Sodium Salt

54. Aprol

55. Nixal

56. Cas-26159-34-2

57. Causalon Pro

58. Naproxen Natrium

59. Naprux Gesic

60. Axer Alfa

61. Dsstox_cid_25576

62. Dsstox_rid_80973

63. Dsstox_gsid_45576

64. Sodium (2s)-2-(6-methoxy-2-naphthyl)propanoate

65. A-nox

66. Anaprox Ds

67. Naproxensodium

68. Sunprox

69. Flanax

70. Naproxen Sodium [usan]

71. Einecs 247-486-2

72. Mfcd00058507

73. Unm-0000306098

74. Rs 3650

75. Topcare All Day Pain Relief

76. Unii-9tn87s3a3c

77. Naproxen Sodium [usan:usp]

78. Bay H6689

79. Naproxen (aleve)

80. Sodium (-)-2-(6-methoxy-2-naphthyl)propionate

81. Anaprox (tn)

82. Naproxen Sodium,(s)

83. Naproxen Sodium (usp)

84. L-(-)-6-methoxy-alpha-methyl-2-naphthaleneacetic Acid Sodium Salt

85. Opera_id_1200

86. Lopac-m-1275

87. Schembl7361

88. Mls001076076

89. Mls001424214

90. Naproxen Sodium [vandf]

91. Chembl1200806

92. Dtxsid7045576

93. Naproxen Sodium [mart.]

94. Naproxen Sodium [usp-rs]

95. Naproxen Sodium [who-dd]

96. Naproxen Sodium Salt [mi]

97. Hms1570o04

98. Hms2052g05

99. Hms2230d08

100. Hms3262o06

101. Hms3269j19

102. Hms3413p03

103. Hms3884g04

104. Tox21_110774

105. Tox21_500792

106. Hy-15030a

107. Naproxen Sodium, 98.0-102.0%

108. Naproxen Sodium [ep Impurity]

109. Naproxen Sodium [orange Book]

110. 2-naphthaleneacetic Acid, 6-methoxy-.alpha.-methyl-, Sodium Salt, (s)-

111. Akos015895696

112. Akos015994759

113. Naproxen Sodium [ep Monograph]

114. Naproxen Sodium [usp Impurity]

115. Tox21_110774_1

116. Bcp9000977

117. Ccg-101082

118. Ks-5141

119. Lp00792

120. Naproxen Sodium [usp Monograph]

121. 2-naphthaleneacetic Acid, 6-methoxy-alpha-methyl-, Sodium Salt, L-(-)-

122. Aleve-d Component Naproxen Sodium

123. Ncgc00016166-01

124. Ncgc00016759-04

125. Ncgc00017097-02

126. Ncgc00094127-01

127. Ncgc00261477-01

128. Treximet Component Naproxen Sodium

129. Bcp0726000300

130. Naproxen Sodium Component Of Aleve-d

131. Eu-0100792

132. M3406

133. Naproxen Sodium Component Of Treximet

134. S1626

135. Sw197105-3

136. 59n342

137. Bim-0050769.0001

138. D00970

139. M 1275

140. Sodium (s)-2-(6-methoxy-2-naphthyl)propionate

141. A818221

142. Naproxen Sodium, Meets Usp Testing Specifications

143. Sodium(s)-2-(6-methoxynaphthalen-2-yl)propanoate

144. W-107195

145. Q27107504

146. (2s)-2-(6-methoxy(2-naphthyl))propanoic Acid Sodium Salt

147. (2s)-2-(6-methoxy-2-naphthyl)propanoic Acid Sodium Salt

148. (s)-6-methoxy-alpha-methyl-2-naphthaleneacetic Acid Sodium

149. Naproxen Sodium, United States Pharmacopeia (usp) Reference Standard

150. 2-naphthaleneacetic Acid, 6-methoxy-.alpha.-methyl-, Sodium Salt, (.alpha.s)- (1:1)

151. Naproxen Sodium, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 252.24 g/mol
Molecular Formula C14H13NaO3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass252.07623855 g/mol
Monoisotopic Mass252.07623855 g/mol
Topological Polar Surface Area49.4 Ų
Heavy Atom Count18
Formal Charge0
Complexity282
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 12  
Drug NameAleve
Active IngredientNaproxen sodium
Dosage FormTablet
RouteOral
Strengtheq 200mg base
Market StatusOver the Counter
CompanyBayer

2 of 12  
Drug NameAnaprox
Drug LabelNaproxen is a proprionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs.The chemical names for naproxen and naproxen sodium are (S)-6-methoxy--methyl-2-naphthaleneacetic acid and (S)-6-methoxy--methyl...
Active IngredientNaproxen sodium
Dosage FormTablet
RouteOral
Strengtheq 250mg base
Market StatusPrescription
CompanyHoffmann La Roche

3 of 12  
Drug NameAnaprox ds
Drug LabelNaproxen is a proprionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs.The chemical names for naproxen and naproxen sodium are (S)-6-methoxy--methyl-2-naphthaleneacetic acid and (S)-6-methoxy--methyl...
Active IngredientNaproxen sodium
Dosage FormTablet
RouteOral
Strengtheq 500mg base
Market StatusPrescription
CompanyHoffmann La Roche

4 of 12  
Drug NameNaprelan
Drug LabelNAPRELAN* Tablets contain naproxen sodium, a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). NAPRELAN Tablets use the proprietary IPDAS** (Intestinal Protective Drug Absorption System) technology. It is a r...
Active IngredientNaproxen sodium
Dosage FormTablet, extended release
RouteOral
Strengtheq 750mg base; eq 500mg base; eq 375mg base
Market StatusPrescription
CompanyAlmatica Pharma

5 of 12  
Drug NameNaprosyn
Drug LabelNaproxen is a proprionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs.The chemical names for naproxen and naproxen sodium are (S)-6-methoxy--methyl-2-naphthaleneacetic acid and (S)-6-methoxy--methyl...
Active IngredientNaproxen
Dosage FormTablet; Suspension
RouteOral
Strength250mg; 375mg; 500mg; 25mg/ml
Market StatusPrescription
CompanyRoche Palo

6 of 12  
Drug NameNaproxen sodium
Drug LabelNAPRELAN* Tablets contain naproxen sodium, a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). NAPRELAN Tablets use the proprietary IPDAS** (Intestinal Protective Drug Absorption System) technology. It is a r...
Active IngredientNaproxen sodium
Dosage FormTablet, extended release; Tablet; Capsule
RouteOral
Strengtheq 500mg base; eq 250mg base; eq 200mg base; eq 375mg base
Market StatusOver the Counter; Prescription
CompanyMarksans Pharma; Actavis Labs Fl; Teva; Aurobindo Pharma; Banner Pharmacaps; Granules India; Hikma; Amneal Pharms Ny; Glenmark Generics; Perrigo; Contract Pharmacal; Ranbaxy Labs; Dr Reddys Labs

7 of 12  
Drug NameAleve
Active IngredientNaproxen sodium
Dosage FormTablet
RouteOral
Strengtheq 200mg base
Market StatusOver the Counter
CompanyBayer

8 of 12  
Drug NameAnaprox
Drug LabelNaproxen is a proprionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs.The chemical names for naproxen and naproxen sodium are (S)-6-methoxy--methyl-2-naphthaleneacetic acid and (S)-6-methoxy--methyl...
Active IngredientNaproxen sodium
Dosage FormTablet
RouteOral
Strengtheq 250mg base
Market StatusPrescription
CompanyHoffmann La Roche

9 of 12  
Drug NameAnaprox ds
Drug LabelNaproxen is a proprionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs.The chemical names for naproxen and naproxen sodium are (S)-6-methoxy--methyl-2-naphthaleneacetic acid and (S)-6-methoxy--methyl...
Active IngredientNaproxen sodium
Dosage FormTablet
RouteOral
Strengtheq 500mg base
Market StatusPrescription
CompanyHoffmann La Roche

10 of 12  
Drug NameNaprelan
Drug LabelNAPRELAN* Tablets contain naproxen sodium, a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). NAPRELAN Tablets use the proprietary IPDAS** (Intestinal Protective Drug Absorption System) technology. It is a r...
Active IngredientNaproxen sodium
Dosage FormTablet, extended release
RouteOral
Strengtheq 750mg base; eq 500mg base; eq 375mg base
Market StatusPrescription
CompanyAlmatica Pharma

11 of 12  
Drug NameNaprosyn
Drug LabelNaproxen is a proprionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs.The chemical names for naproxen and naproxen sodium are (S)-6-methoxy--methyl-2-naphthaleneacetic acid and (S)-6-methoxy--methyl...
Active IngredientNaproxen
Dosage FormTablet; Suspension
RouteOral
Strength250mg; 375mg; 500mg; 25mg/ml
Market StatusPrescription
CompanyRoche Palo

12 of 12  
Drug NameNaproxen sodium
Drug LabelNAPRELAN* Tablets contain naproxen sodium, a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). NAPRELAN Tablets use the proprietary IPDAS** (Intestinal Protective Drug Absorption System) technology. It is a r...
Active IngredientNaproxen sodium
Dosage FormTablet, extended release; Tablet; Capsule
RouteOral
Strengtheq 500mg base; eq 250mg base; eq 200mg base; eq 375mg base
Market StatusOver the Counter; Prescription
CompanyMarksans Pharma; Actavis Labs Fl; Teva; Aurobindo Pharma; Banner Pharmacaps; Granules India; Hikma; Amneal Pharms Ny; Glenmark Generics; Perrigo; Contract Pharmacal; Ranbaxy Labs; Dr Reddys Labs

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)


Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)


Gout Suppressants

Agents that increase uric acid excretion by the kidney (URICOSURIC AGENTS), decrease uric acid production (antihyperuricemics), or alleviate the pain and inflammation of acute attacks of gout. (See all compounds classified as Gout Suppressants.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Histamine H1 Receptor Antagonists [MoA]; Histamine-1 Receptor Antagonist [EPC]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
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  • TABLET;ORAL - EQ 250MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
  • TABLET;ORAL - EQ 500MG BASE
  • TABLET;ORAL - 220MG
  • TABLET, EXTENDED RELEASE;ORAL - EQ 375MG BASE
  • TABLET, EXTENDED RELEASE;ORAL - EQ 500MG BASE
  • TABLET, EXTENDED RELEASE;ORAL - EQ 750MG BASE
  • CAPSULE;ORAL - EQ 200MG BASE
  • TABLET;ORAL - 500MG;EQ 85MG BASE
  • TABLET;ORAL - 60MG;EQ 10MG BASE
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