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Also known as: 5-aminosalicylic acid, Mesalazine, 89-57-6, 5-amino-2-hydroxybenzoic acid, Asacol, Pentasa
Molecular Formula
C7H7NO3
Molecular Weight
153.14  g/mol
InChI Key
KBOPZPXVLCULAV-UHFFFAOYSA-N
FDA UNII
4Q81I59GXC

Mesalazine
An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed)
Mesalamine is an Aminosalicylate.
1 2D Structure

Mesalazine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-amino-2-hydroxybenzoic acid
2.1.2 InChI
InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
2.1.3 InChI Key
KBOPZPXVLCULAV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1N)C(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
4Q81I59GXC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5 Aminosalicylate

2. 5 Aminosalicylic Acid

3. 5-aminosalicylate

4. 5-aminosalicylic Acid

5. Asacol

6. Asacolon

7. Ascolitin

8. Canasa

9. Claversal

10. Fivasa

11. Hydrochloride, Mesalamine

12. Lixacol

13. M Aminosalicylic Acid

14. M-aminosalicylic Acid

15. Mesalamine Hydrochloride

16. Mesalamine Monosodium Salt

17. Mesalazine

18. Mesasal

19. Meta Aminosalicylic Acid

20. Meta-aminosalicylic Acid

21. Monosodium Salt, Mesalamine

22. Novo 5 Asa

23. Novo-5 Asa

24. Pentasa

25. Rowasa

26. Salofalk

2.3.2 Depositor-Supplied Synonyms

1. 5-aminosalicylic Acid

2. Mesalazine

3. 89-57-6

4. 5-amino-2-hydroxybenzoic Acid

5. Asacol

6. Pentasa

7. Canasa

8. 5-asa

9. Claversal

10. Rowasa

11. Salofalk

12. M-aminosalicylic Acid

13. Lialda

14. Mesasal

15. Benzoic Acid, 5-amino-2-hydroxy-

16. Fisalamine

17. Apriso

18. Lixacol

19. Sfrowasa

20. P-aminosalicylsaeure

21. Asacolitin

22. Mesalazina

23. Mesalazinum

24. Iialda

25. 5-amino-2-hydroxy-benzoic Acid

26. Asacol Hd

27. Mesalamine [usan]

28. 5-amino Salicylic Acid

29. Salicylic Acid, 5-amino-

30. 2-hydroxy-5-aminobenzoic Acid

31. Max-002

32. 3-carboxy-4-hydroxyaniline

33. Mfcd00007877

34. Nsc 38877

35. Nsc-38877

36. Mesalazine [inn]

37. Mls001424012

38. 4q81i59gxc

39. Chebi:6775

40. Mesalamine (usan)

41. 5-?aminosalicylic Acid (mesalazine)

42. Cas-89-57-6

43. Ncgc00016344-03

44. Mesalazinum [latin]

45. Smr000145728

46. Dsstox_cid_4506

47. Dsstox_rid_77435

48. Dsstox_gsid_24506

49. Mesalazina [spanish]

50. P-aminosalicylsaeure [german]

51. Mesavancol

52. Delzicol

53. Mesavance

54. Mezavant

55. Mesalazine Mmx

56. Mezavant Xl

57. Mesalamine (usp)

58. Pentasa (tn)

59. Salofalk Granu-stix

60. Apriso (tn)

61. Asacol (tn)

62. Canasa (tn)

63. Lialda (tn)

64. Rowasa (tn)

65. 5-as

66. Ccris 7334

67. Sr-01000763486

68. Mesalamine [usan:usp]

69. Einecs 201-919-1

70. Brn 2090421

71. Unii-4q81i59gxc

72. Ai3-15564

73. Hsdb 7512

74. Ajg-501

75. Spd 476

76. Spd-476

77. Spd-480

78. Mesalamine (tn)

79. Delzicol (tn)

80. Sfrowasa (tn)

81. Mesalamine (lialda)

82. 5-aminosalicylic_acid

83. Md-0901

84. 5-aminosalicyclic Acid

85. 5-amino-salicylic Acid

86. Mesalamine [mi]

87. Mesalazine [jan]

88. Prestwick0_001069

89. Prestwick1_001069

90. Prestwick2_001069

91. Prestwick3_001069

92. Mesalamine [hsdb]

93. Wln: Zr Dq Cvq

94. Z-206

95. Mesalamine [vandf]

96. Chembl704

97. Mesalazine (jp17/inn)

98. Ec 201-919-1

99. Cid_4075

100. Mesalazine [mart.]

101. Mesalamine [usp-rs]

102. Mesalazine [who-dd]

103. Oprea1_847633

104. Schembl31297

105. 3amino-6-hydroxybenzoic Acid

106. Bspbio_001058

107. Kbiogr_002425

108. Kbioss_002431

109. 4-14-00-02058 (beilstein Handbook Reference)

110. Mls000758287

111. 5-aminosalicylic Acid, 95%

112. 5-aminosalicylic Acid, Tablet

113. Bidd:gt0811

114. 3-amino-6-hydroxybenzoic Acid

115. Spbio_002969

116. Bpbio1_001164

117. Gtpl2700

118. Zinc1688

119. 5-amino 2-hydroxy Benzoic Acid

120. Dtxsid5024506

121. Mesalamine [orange Book]

122. Mesalazine [ep Impurity]

123. Schembl18038934

124. 5-aminosalicylic Acid, >=99%

125. Bdbm60918

126. Kbio2_002425

127. Kbio2_004993

128. Kbio2_007561

129. Kbio3_002904

130. Mesalazine [ep Monograph]

131. Cmap_000045

132. Hms1571e20

133. Hms2051m21

134. Hms2090i09

135. Hms2098e20

136. Hms3393m21

137. Hms3649k15

138. Hms3651m15

139. Hms3715e20

140. Mesalamine [usp Monograph]

141. Pharmakon1600-01505993

142. Bcp05326

143. Nsc38877

144. Tox21_110384

145. Tox21_201610

146. Tox21_303125

147. Ac8101

148. Bbl013046

149. Nsc759301

150. S1681

151. Stk301678

152. Akos000118959

153. Tox21_110384_1

154. Ac-2764

155. Bcp9000175

156. Ccg-100829

157. Db00244

158. Hs-0100

159. Nc00079

160. Nsc-759301

161. Ncgc00016344-01

162. Ncgc00016344-02

163. Ncgc00016344-04

164. Ncgc00016344-05

165. Ncgc00016344-07

166. Ncgc00090934-01

167. Ncgc00090934-02

168. Ncgc00257142-01

169. Ncgc00259159-01

170. 5-amino-2-hydroxobenzoic Acid Monohydrate

171. Bp-13074

172. Hy-15027

173. Sy002854

174. 5-aminosalicylic Acid, Analytical Standard

175. A0317

176. Ab00374979

177. Am20060091

178. Ft-0619950

179. Sw197303-4

180. C07138

181. D00377

182. Ab00374979-09

183. Ab00374979-10

184. Ab00374979_11

185. Ab00374979_12

186. Q412479

187. 5-amino-2-hydroxybenzoic Acid,5-aminosalicylic Acid

188. Q-201355

189. Sr-01000763486-3

190. Sr-01000763486-4

191. Sr-01000763486-9

192. Z57127471

193. F1918-0003

194. Mesalazine, European Pharmacopoeia (ep) Reference Standard

195. Mesalamine, United States Pharmacopeia (usp) Reference Standard

196. Mesalamine, Pharmaceutical Secondary Standard; Certified Reference Material

197. Mesalazine For System Suitability, European Pharmacopoeia (ep) Reference Standard

198. 51481-17-5

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 153.14 g/mol
Molecular Formula C7H7NO3
XLogP31.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass153.042593085 g/mol
Monoisotopic Mass153.042593085 g/mol
Topological Polar Surface Area83.6 Ų
Heavy Atom Count11
Formal Charge0
Complexity160
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 20  
Drug NameApriso
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach APRISO capsule is a delayed- and extended-release dosage form for oral administration. Each capsule contains 0.375 g of mesalamine USP (5-aminosalicylic acid, 5-ASA), an anti-inflammatory drug. The structural formula of mesalamine is: Molecula...
Active IngredientMesalamine
Dosage FormCapsule, extended release
RouteOral
Strength375mg
Market StatusPrescription
CompanySalix Pharms

2 of 20  
Drug NameAsacol
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach Asacol delayed release tablet for oral administration contains 400mg of mesalamine, an anti-inflammatory drug. The Asacol delayed-release tablets are coated with acrylic based resin, Eudragit S (methacrylic acid copolymer B, NF), which dissolves...
Active IngredientMesalamine
Dosage FormTablet, delayed release
RouteOral
Strength400mg
Market StatusPrescription
CompanyWarner Chilcott

3 of 20  
Drug NameAsacol hd
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach Asacol HD delayed-release tablet for oral administration contains 800 mg of mesalamine, an aminosalicylate. Asacol HD delayed-release tablets have an outer protective coat consisting of a combination of acrylic based resins, Eudragit S (methacry...
Active IngredientMesalamine
Dosage FormTablet, delayed release
RouteOral
Strength800mg
Market StatusPrescription
CompanyWarner Chilcott

4 of 20  
Drug NameCanasa
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelThe active ingredient in CANASA 1000 mg rectal suppositories is mesalamine, also known as mesalazine or 5-aminosalicylic acid (5-ASA). Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid, and is classified as an anti-inflammatory drug. Each CANAS...
Active IngredientMesalamine
Dosage FormSuppository
RouteRectal
Strength1gm
Market StatusPrescription
CompanyForest Labs

5 of 20  
Drug NameDelzicol
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach DELZICOL (mesalamine) delayed-release capsule for oral administration contains 400 mg of mesalamine, an aminosalicylate. DELZICOL (mesalamine) delayed-release capsules contain acrylic based resin, Eudragit S (methacrylic acid copolymer type B, N...
Active IngredientMesalamine
Dosage FormCapsule, delayed release
RouteOral
Strength400mg
Market StatusPrescription
CompanyWarner Chilcott

6 of 20  
Drug NameLialda
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach LIALDA delayed-release tablet for oral administration contains 1.2 g 5-aminosalicylic acid (5-ASA; mesalamine), an anti-inflammatory agent. Mesalamine also has the chemical name 5-amino-2-hydroxybenzoic acid and its structural formula is:Molecul...
Active IngredientMesalamine
Dosage FormTablet, delayed release
RouteOral
Strength1.2gm
Market StatusPrescription
CompanyShire

7 of 20  
Drug NameMesalamine
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelThe active ingredient in ROWASA (mesalamine) Rectal Suspension Enema, a disposable (60 mL) unit, is mesalamine, also known as 5-aminosalicylic acid (5-ASA). Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid.The empirical formula is C7H7NO3, r...
Active IngredientMesalamine
Dosage FormEnema
RouteRectal
Strength4gm/60ml
Market StatusPrescription
CompanyTeva; Perrigo Israel

8 of 20  
Drug NamePentasa
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelPENTASA (mesalamine) for oral administration is a controlled-release formulation of mesalamine, an aminosalicylate anti-inflammatory agent for gastrointestinal use.Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid. It has a molecular weight of...
Active IngredientMesalamine
Dosage FormCapsule, extended release
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyShire

9 of 20  
Drug NameRowasa
Drug LabelThe active ingredient in ROWASA (mesalamine) Rectal Suspension Enema, a disposable (60 mL) unit, is mesalamine, also known as 5-aminosalicylic acid (5-ASA). Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid.The empirical formula is C7H7NO3, r...
Active IngredientMesalamine
Dosage FormEnema
RouteRectal
Strength4gm/60ml
Market StatusPrescription
CompanyMeda Pharms

10 of 20  
Drug NameSfrowasa
Active IngredientMesalamine
Dosage FormEnema
RouteRectal
Strength4gm/60ml
Market StatusPrescription
CompanyMeda Pharms

11 of 20  
Drug NameApriso
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach APRISO capsule is a delayed- and extended-release dosage form for oral administration. Each capsule contains 0.375 g of mesalamine USP (5-aminosalicylic acid, 5-ASA), an anti-inflammatory drug. The structural formula of mesalamine is: Molecula...
Active IngredientMesalamine
Dosage FormCapsule, extended release
RouteOral
Strength375mg
Market StatusPrescription
CompanySalix Pharms

12 of 20  
Drug NameAsacol
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach Asacol delayed release tablet for oral administration contains 400mg of mesalamine, an anti-inflammatory drug. The Asacol delayed-release tablets are coated with acrylic based resin, Eudragit S (methacrylic acid copolymer B, NF), which dissolves...
Active IngredientMesalamine
Dosage FormTablet, delayed release
RouteOral
Strength400mg
Market StatusPrescription
CompanyWarner Chilcott

13 of 20  
Drug NameAsacol hd
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach Asacol HD delayed-release tablet for oral administration contains 800 mg of mesalamine, an aminosalicylate. Asacol HD delayed-release tablets have an outer protective coat consisting of a combination of acrylic based resins, Eudragit S (methacry...
Active IngredientMesalamine
Dosage FormTablet, delayed release
RouteOral
Strength800mg
Market StatusPrescription
CompanyWarner Chilcott

14 of 20  
Drug NameCanasa
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelThe active ingredient in CANASA 1000 mg rectal suppositories is mesalamine, also known as mesalazine or 5-aminosalicylic acid (5-ASA). Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid, and is classified as an anti-inflammatory drug. Each CANAS...
Active IngredientMesalamine
Dosage FormSuppository
RouteRectal
Strength1gm
Market StatusPrescription
CompanyForest Labs

15 of 20  
Drug NameDelzicol
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach DELZICOL (mesalamine) delayed-release capsule for oral administration contains 400 mg of mesalamine, an aminosalicylate. DELZICOL (mesalamine) delayed-release capsules contain acrylic based resin, Eudragit S (methacrylic acid copolymer type B, N...
Active IngredientMesalamine
Dosage FormCapsule, delayed release
RouteOral
Strength400mg
Market StatusPrescription
CompanyWarner Chilcott

16 of 20  
Drug NameLialda
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelEach LIALDA delayed-release tablet for oral administration contains 1.2 g 5-aminosalicylic acid (5-ASA; mesalamine), an anti-inflammatory agent. Mesalamine also has the chemical name 5-amino-2-hydroxybenzoic acid and its structural formula is:Molecul...
Active IngredientMesalamine
Dosage FormTablet, delayed release
RouteOral
Strength1.2gm
Market StatusPrescription
CompanyShire

17 of 20  
Drug NameMesalamine
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelThe active ingredient in ROWASA (mesalamine) Rectal Suspension Enema, a disposable (60 mL) unit, is mesalamine, also known as 5-aminosalicylic acid (5-ASA). Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid.The empirical formula is C7H7NO3, r...
Active IngredientMesalamine
Dosage FormEnema
RouteRectal
Strength4gm/60ml
Market StatusPrescription
CompanyTeva; Perrigo Israel

18 of 20  
Drug NamePentasa
PubMed HealthMesalamine
Drug ClassesAnti-Inflammatory, Gastrointestinal Agent
Drug LabelPENTASA (mesalamine) for oral administration is a controlled-release formulation of mesalamine, an aminosalicylate anti-inflammatory agent for gastrointestinal use.Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid. It has a molecular weight of...
Active IngredientMesalamine
Dosage FormCapsule, extended release
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyShire

19 of 20  
Drug NameRowasa
Drug LabelThe active ingredient in ROWASA (mesalamine) Rectal Suspension Enema, a disposable (60 mL) unit, is mesalamine, also known as 5-aminosalicylic acid (5-ASA). Chemically, mesalamine is 5-amino-2-hydroxybenzoic acid.The empirical formula is C7H7NO3, r...
Active IngredientMesalamine
Dosage FormEnema
RouteRectal
Strength4gm/60ml
Market StatusPrescription
CompanyMeda Pharms

20 of 20  
Drug NameSfrowasa
Active IngredientMesalamine
Dosage FormEnema
RouteRectal
Strength4gm/60ml
Market StatusPrescription
CompanyMeda Pharms

4.2 Therapeutic Uses

Mesalamine rectal suspension is indicated for the treatment of mild to moderate distal ulcerative colitis, proctosigmoiditis, and proctitis. /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1934


Mesalamine rectal suspension is indicated to help maintain remission of distal ulcerative colitis. /NOT included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1934


Mesalamine suppositories are indicated for the treatment of active ulcerative proctitis. /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1934


Mesalamine is indicated to treat and to maintain remission of mild to moderate ulcerative colitis or (Crohn's disease). /Included in US product labeling/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1931


Lialda /the first oral once daily mesalamine tablet/ is indicated for the induction of remission in patients with active, mild to moderate ulcerative colitis.

FDA: Center for Drug Evaluation and Research (CDER); Label Information for Lialda (Mesalamine) Lasted updated 2007. Available from, as of March 30, 2007: https://www.fda.gov/cder/foi/label/2007/022000lbl.pdf


4.3 Drug Warning

Oral and rectal mesalamine preparations usually are well tolerated. The most common adverse effects of oral or rectal mesalamine are GI effects and headache. In clinical studies, most adverse effects associated with oral or rectal preparations were mild in severity and were transient or reversible. However, adverse effects have been severe enough to require discontinuance of the drug in less than 1% or in up to about 4-5% of patients receiving rectal or oral mesalamine, respectively, although in some studies, the rate of discontinuance of the drug was similar to or less than in those receiving placebo. Most of the adverse effects reported with the use of oral mesalamine delayed-release tablets were similar in short- and long-term studies.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3013


Exacerbation of colitis symptoms was reported in 3% of patients receiving oral mesalamine delayed-release tablets. Other adverse GI effects associated with oral mesalamine extended-release capsules and occurring in less than 1% of patients, include abdominal distention, constipation, duodenal ulcer, dysphagia, eructation, esophageal or mouth ulcer, fecal incontinence, GI bleeding (e.g., rectal bleeding), stool abnormalities (e.g., change in color or texture), oral moniliasis, and thirst, although a causal relationship to the drug of many of these adverse effects has not been established.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3013


In controlled clinical trials in patients receiving oral mesalamine delayed-release tablets, abdominal pain, eructation, nausea, diarrhea, dyspepsia, vomiting, constipation, flatulence, exacerbation of colitis, abdominal enlargement, gastroenteritis, GI hemorrhage, rectal disorder (e.g., hemorrhage, tenesmus), and stool abnormalities, were the most common adverse GI effects, occurring in about 2-18% of patients; dry mouth, indigestion, stomatitis, and cramping were reported rarely. Frequency of these GI effects did not seem to increase with increased dosages, although in uncontrolled studies, the incidence of abdominal pain, flatulence, and GI bleeding were dose related. The most common adverse GI effects of oral mesalamine extended-released capsules were diarrhea (including melena), nausea, abdominal pain, dyspepsia, vomiting, anorexia, worsening of ulcerative colitis, and rectal urgency, occurring in greater than 0.4-3% of patients.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3013


An acute intolerance syndrome (sensitivity reaction), characterized by cramping, abdominal pain, bloody diarrhea, and, occasionally, fever, headache, malaise, conjunctivitis, pruritus, and rash, has occurred in a few patients receiving mesalamine and required prompt discontinuance of the drug. In patients manifesting such intolerance, a history of sulfasalazine intolerance, if any, should be reevaluated.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3014


For more Drug Warnings (Complete) data for MESALAMINE (26 total), please visit the HSDB record page.


4.4 Drug Indication

Mesalazine is indicated for the induction of remission in patients with active or mild to moderate acute exacerbations of ulcerative colitis and for the maintenance of remission of ulcerative colitis,. Prescribing information for mesalazine in the UK also indicates the medication for the maintenance of remission of Crohn's ileo-colitis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Mesalazine is one of the two components of sulphasalazine, the other being sulphapyridine. It is the latter which is responsible for the majority of the side effects associated with sulphasalazine therapy whilst mesalazine is known to be the active moiety in the treatment of ulcerative colitis. The pharmacodynamic actions of mesalazine occur in the colonic/rectal mucosae local to the delivery of drug from mesalazine tablets into the lumen. There is information suggesting that the severity of colonic inflammation in ulcerative colitis patients treated with mesalazine is inversely correlated with mucosal concentrations of mesalazine. Plasma concentrations representing systemically absorbed mesalazine are not believed to contribute extensively to efficacy.


5.2 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
MESALAMINE
5.3.2 FDA UNII
4Q81I59GXC
5.3.3 Pharmacological Classes
Aminosalicylic Acids [CS]; Aminosalicylate [EPC]
5.4 ATC Code

A07EC02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


A - Alimentary tract and metabolism

A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

A07E - Intestinal antiinflammatory agents

A07EC - Aminosalicylic acid and similar agents

A07EC02 - Mesalazine


5.5 Absorption, Distribution and Excretion

Absorption

Depending on the formulation administered, prescribing information for orally administered delayed-released tablets of 2.4g or 4.8g of mesalazine given once daily for 14 days to healthy volunteers was to found to be about 21% to 22% of the administered dose while prescribing information for an orally administered controlled-release capsule formulation suggests 20% to 30% of the mesalazine in the formulation is absorbed. In contrast, when mesalamine is administered orally as an unformulated 1-g aqueous suspension, mesalazine is approximately 80% absorbed.


Route of Elimination

Elimination of mesalazine is mainly via the renal route following metabolism to N-acetyl-5-aminosalicylic acid (acetylation). However, there is also limited excretion of the parent mesalazine drug in the urine. After the oral administration of the extended-release formulation of mesalazine, of the approximately 21% to 22% of the drug absorbed, less than 8% of the dose was excreted unchanged in the urine after 24 hours, compared with greater than 13% for N-acetyl-5-aminosalicylic acid. When given the controlled-release formulation, about 130 mg free mesalazine was recovered in the feces following a single 1-g dose, which was comparable to the 140 mg of mesalazine recovered from the molar equivalent sulfasalazine tablet dose of 2.5 g F3001]. Elimination of free mesalazine and salicylates in feces increased proportionately with the dose given. N-acetylmesalazine was the primary compound excreted in the urine (19% to 30%) following the controlled-release dosing.


Volume of Distribution

The apparent volume of distribution (Vd) of the drug in adults is approximately 0.2 L/kg.


Clearance

The mean (SD) renal clearance in L/h for mesalazine following the single dose administration of mesalazine delayed-release tablets 4.8g under fasting conditions to young and elderly subjects was documented as 2.05 (1.33) in young subjects aged 18 to 35 years old, 2.04 (1.16) in elderly subjects aged 65 to 75 years old, and 2.13 (1.20) in elderly subjects older than 75 years.


Following oral administration, low concentrations of mesalamine and higher concentrations of its metabolite, N-acetyl-5-aminosalicylic acid, have been detected in human breast milk. It is not known whether mesalamine or its metabolites are distributed into milk in humans following rectal administration.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3017


Mesalamine and N-acetyl-5-aminosalicylic acid cross the placenta following oral administration; however, serum concentrations of mesalamine in umbilical cord and amniotic fluid are very low. It is not known whether mesalamine crosses the placenta following rectal administration.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3017


In vitro, mesalamine and N-acetyl-5-aminosalicylic acid are approximately 44-55 and 80% bound, respectively, to plasma proteins. Protein binding of N-acetyl-5-aminosalicylic acid does not appear to be concentration dependent at concentrations ranging from 1-10 ug/mL.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3017


It is generally accepted that 5-aminosalicylate (5-ASA; mesalamine), widely used in inflammatory bowel disease therapy, exerts its action from the intraluminal site of the intestine. In addition to local metabolism of 5-ASA, it has been assumed that therapeutic mucosal concentrations of 5-ASA depend on transporter-mediated secretion back to the lumen. ... The hypothesis that 5-ASA represents a substrate of P-glycoprotein (P-gp) and/or multidrug resistance-associated protein 2 (MRP2), thereby possibly contributing to variable therapeutic effects /was tested/. Polarized, basal-to-apical transport of [(3)H]5-ASA was studied in monolayers of Caco-2 and L-MDR cells, both of which express P-gp in their apical membrane, as well as in MDCK cells transfected with human MRP2. Moreover, we investigated the influence of 5-ASA on transport of digoxin in Caco-2 cells. In Caco-2 cells a P-gp-mediated efflux of 5-ASA (5-500 muM) could be excluded. Likewise, in L-MDR1 and MRP2 cells no transport differences in either the basal-to-apical or apical-to-basal direction were measurable. 5-ASA (50 muM to 5 mM) had no effect on the transport of digoxin. ...

PMID:16944117 Xin HW et al; Eur J Clin Pharmacol 62 (10): 871-875 (2006)


For more Absorption, Distribution and Excretion (Complete) data for MESALAMINE (15 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

The primary metabolite of mesalazine (5-aminosalicylic acid) is predominantly N-acetyl-5-aminosalicylic acid (Ac-5-ASA). This metabolite is generated via N-acetyltransferase (NAT) activity in the liver and intestinal mucosa cells, largely by NAT-1, in particular.


Mesalazine (5-aminosalicylic acid, 5-ASA), an anti-inflammatory agent for the treatment of inflammatory bowel diseases, is metabolized in organism to the principal biotransformation product, N-acetyl-5-ASA. Some other phase II metabolites (N-formyl-5-ASA, N-butyryl-5-ASA, N-beta-d-glucopyranosyl-5-ASA) have also been described. 5-ASA is a polar compound and besides it exhibits amphoteric properties. ...

PMID:16466733 Nobilis M et al; J Chromatogr A 1119 (1-2): 299-308 (2006)


The exact metabolic fate of mesalamine has not been clearly established. The drug undergoes rapid N-acetylation, probably in the liver, to form N-acetyl-5-aminosalicylic acid; mesalamine and N-acetyl-5-aminosalicylic acid also may undergo conjugation with glucuronic acid. Several other, unidentified metabolites also may be formed. It has been suggested that N-acetylation also may occur (to a limited extent) in the intestinal wall and/or the lumen. The intestinal flora probably are involved in this acetylation, and extensive floral acetylation may adversely affect clinical efficacy of the drug. Correlation between acetylator phenotype of patients receiving mesalamine and the degree of N-acetylation does not appear to exist. Although it has been suggested that N-acetyl-5-aminosalicylic acid may be pharmacologically active, therapeutic response has been poor in some patients treated rectally with this metabolite, and the relative contribution of this metabolite to the therapeutic effect of mesalamine remains questionable. N-Acetyl-5-aminosalicylic acid did not inhibit lipoxygenase in vitro.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2007., p. 3017


Mesalazine has known human metabolites that include mesalazine, N-acetyl.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

The apparent elimination half-life documented for oral delayed-release mesalazine tablets is 7 to 12 hours. The elimination half-life recorded for the active N-acetyl-5-aminosalicylic acid metabolite generated from the administration of oral delayed-release mesalazine tablets is 12 to 23 hours.


Elimination of metabolite: 5 to 10 hr /N-acetyl-5-aminosalicylci acid/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1934


Elimination: 0.5-1.5 hours

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1934


5.8 Mechanism of Action

Although the mechanism of action of mesalazine is not fully understood, it is believed to possess a topical anti-inflammatory effect on colonic epithelial cells. Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase pathways, i.e., prostanoids, and through the lipoxygenase pathways, i.e., leukotrienes and hydroxyeicosatetraenoic acids, is increased in patients with chronic inflammatory bowel disease, and it is possible that mesalazine diminishes inflammation by blocking cyclooxygenase and inhibiting prostaglandin production in the colon. Furthermore, mesalazine also has the potential to inhibit the activation of Nuclear Factor kappa B (NKkB) and consequently the production of key of pro-inflammatory cytokines. It has been proposed that reduced expression of PPAR gamma nuclear receptors (gamma form of peroxisome proliferator-activated receptors) may be implicated in ulcerative colitis. There is evidence that mesalazine produces pharmacodynamic effects through direct activation of PPAR gamma receptors in the colonic/rectal epithelium as well. Moreover, since increased leukocyte migration, abnormal cytokine production, increased production of arachidonic acid metabolites, particularly leukotriene B4, and increased free radical formation in the inflamed intestinal tissue are all present in patients with inflammatory bowel disease it is also believed that mesalazine has in-vitro and in-vivo pharmacological effects that inhibit leukocyte chemotaxis, decrease cytokine and leukotriene production and scavenge for free radicals.


Mesalamine is effective in the treatment of inflammatory bowel diseases. However, the mechanisms of action of mesalamine remain unclear. IEC-6 and IRD-98, nontransformed rat small intestinal epithelial cell lines, were used to examine the effect of mesalamine on the expression of manganese superoxide dismutase (MnSOD). Rats were given mesalamine enemas to determine the effect on colonic MnSOD expression. Treatment with mesalamine at 0.02 or 2 mg/mL induced MnSOD mRNA levels 2.67-fold or 5.66-fold, respectively. Inhibition of 5-lipoxygenase activating protein with MK-886 or cyclooxygenase with indomethacin did not influence the level of MnSOD mRNA. Nuclear run-on experiments demonstrated an increase in de novo transcription following treatment with mesalamine. MnSOD protein levels were induced 2-fold at 24 hr and 4.23-fold at 48 hr following treatment with 1 mg/mL mesalamine. Mesalamine increased MnSOD 1.7-fold in vivo. Pretreatment with mesalamine significantly protected IRD-98 cells from tumor necrosis factor-alpha cytotoxicity. This is the first example of transcriptional gene regulation by mesalamine. The induction of MnSOD by mesalamine may contribute to the therapeutic mechanism of mesalamine.

PMID:11557525 Valentine JF; Am J Physiol Gastrointest Liver Physiol 281 (4): G1044-50 (2001)


Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase and lipoxygenase pathways, is increased in patients with inflammatory bowel disease. Mesalamine appears to diminish inflammation by inhibiting cyclooxygenase and lipoxygenase, thereby decreasing the production of prostaglandins, and leukotrienes and hydroxyeicosatetraenoic acids (HETs), respectively. It is also believed that mesalamine acts aas a scavenger of oxygen-derived free radicals, which are produced in greater numbers in patients with inflammatory bowel disease.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 1931


Derivatives of 5-aminosalicylic acid (mesalamine) represent a mainstay in inflammatory bowel disease therapy, yet the precise mechanism of their therapeutic action is unknown. Because tumor necrosis factor (TNF)-alpha is important in the pathogenesis of inflammatory bowel disease, we investigated the effect of mesalamine on TNF-alpha-regulated signal transduction and proliferation in intestinal epithelial cells. Young adult mouse colon cells were studied with TNF-alpha, epidermal growth factor, or ceramide in the presence or absence of mesalamine. Proliferation was studied by hemocytometry. Mitogen-activated protein (MAP) kinase activation and IkappaBalpha expression were determined by Western blot analysis. Nuclear transcription factor kappaB (NF-kappaB) nuclear translocation was determined by confocal laser immunofluorescent microscopy. The antiproliferative effects of TNF-alpha were blocked by mesalamine. TNF-alpha and ceramide activation of MAP kinase were inhibited by mesalamine, whereas epidermal growth factor activation of MAP kinase was unaffected. TNF-alpha-stimulated NF-kappaB activation and nuclear translocation and the degradation of Ikappa-Balpha were blocked by mesalamine. Mesalamine inhibits TNF-alpha-mediated effects on intestinal epithelial cell proliferation and activation of MAP kinase and NF-kappaB. Therefore, it may function as a therapeutic agent based on its ability to disrupt critical signal transduction events in the intestinal cell necessary for perpetuation of the chronic inflammatory state.

PMID:10029619 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3606885 Kaiser GC et al; Gastroenterology 116 (3): 602-9 (1999)


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07-Jan-2021
30-Nov-2024
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Drugs in Development

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Details:

The acquisition will enable Ethypharm a full portfolio of Mesalazine forms, including a suppository form of Etiasa (mesalazine), used to treat IBD such as ulcerative colitis and Crohn's disease.


Lead Product(s): Mesalazine

Therapeutic Area: Gastroenterology Brand Name: Etiasa

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Ethypharm

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Acquisition June 13, 2024

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01

Anbison

China
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Pharma, Lab & Chemical Expo
Not Confirmed

Anbison

China
arrow
Pharma, Lab & Chemical Expo
Not Confirmed

Details : The acquisition will enable Ethypharm a full portfolio of Mesalazine forms, including a suppository form of Etiasa (mesalazine), used to treat IBD such as ulcerative colitis and Crohn's disease.

Brand Name : Etiasa

Molecule Type : Small molecule

Upfront Cash : Undisclosed

June 13, 2024

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Details:

Mesalamine, also known as 5-aminosalicylic acid extended-release capsule is a small molecule, which is indicated for the maintenance of remission of ulcerative colitis in adults.


Lead Product(s): Mesalazine

Therapeutic Area: Gastroenterology Brand Name: Apriso-Generic

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable August 21, 2023

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02

Pharma, Lab & Chemical Expo
Not Confirmed
Pharma, Lab & Chemical Expo
Not Confirmed

Details : Mesalamine, also known as 5-aminosalicylic acid extended-release capsule is a small molecule, which is indicated for the maintenance of remission of ulcerative colitis in adults.

Brand Name : Apriso-Generic

Molecule Type : Small molecule

Upfront Cash : Not Applicable

August 21, 2023

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Details:

Mesalamine Extended-Release capsules are indicated for the maintenance of remission of ulcerative colitis in adults. The drug will be manufactured at the group’s formulation manufacturing facility at the SEZ, Ahmedabad.


Lead Product(s): Mesalazine

Therapeutic Area: Gastroenterology Brand Name: Undisclosed

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable August 13, 2021

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03

Pharma, Lab & Chemical Expo
Not Confirmed
Pharma, Lab & Chemical Expo
Not Confirmed

Details : Mesalamine Extended-Release capsules are indicated for the maintenance of remission of ulcerative colitis in adults. The drug will be manufactured at the group’s formulation manufacturing facility at the SEZ, Ahmedabad.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

August 13, 2021

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Details:

Kyowa Kirin will finish its commercialization activity for ASACOL on March 31, 2020, and Zeria will obtain the full rights of the commercialization activities for ASACOL from April 1, 2020.


Lead Product(s): Mesalazine

Therapeutic Area: Gastroenterology Brand Name: Undisclosed

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Kyowa Kirin

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Agreement February 03, 2020

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04

Pharma, Lab & Chemical Expo
Not Confirmed
Pharma, Lab & Chemical Expo
Not Confirmed

Details : Kyowa Kirin will finish its commercialization activity for ASACOL on March 31, 2020, and Zeria will obtain the full rights of the commercialization activities for ASACOL from April 1, 2020.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Undisclosed

February 03, 2020

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - ENEMA;RECTAL - 4GM/60ML

USFDA APPLICATION NUMBER - 19618

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 250...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 250MG

USFDA APPLICATION NUMBER - 20049

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 500...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 500MG

USFDA APPLICATION NUMBER - 20049

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DOSAGE - CAPSULE, DELAYED RELEASE;ORAL - 400M...DOSAGE - CAPSULE, DELAYED RELEASE;ORAL - 400MG

USFDA APPLICATION NUMBER - 204412

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DOSAGE - SUPPOSITORY;RECTAL - 1GM

USFDA APPLICATION NUMBER - 21252

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DOSAGE - TABLET, DELAYED RELEASE;ORAL - 800MG...DOSAGE - TABLET, DELAYED RELEASE;ORAL - 800MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21830

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DOSAGE - TABLET, DELAYED RELEASE;ORAL - 1.2GM

USFDA APPLICATION NUMBER - 22000

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 375...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 375MG

USFDA APPLICATION NUMBER - 22301

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Patents & EXCLUSIVITIES

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US Patents

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01

ABBVIE

U.S.A
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Pharma, Lab & Chemical Expo
Not Confirmed

MESALAMINE

US Patent Number : 8436051

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 21252

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2028-06-06

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02

ABBVIE

U.S.A
arrow
Pharma, Lab & Chemical Expo
Not Confirmed

MESALAMINE

US Patent Number : 8217083

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 21252

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2028-06-06

Abbvie Company Banner

03

arrow
Pharma, Lab & Chemical Expo
Not Confirmed

SALIX

U.S.A
arrow
Pharma, Lab & Chemical Expo
Not Confirmed

MESALAMINE

US Patent Number : 8865688

Drug Substance Claim :

Drug Product Claim :

Application Number : 22301

Patent Use Code : U-1310

Delist Requested :

Patent Use Description : FOR THE MAINTENANCE OF...

Patent Expiration Date : 2030-05-01

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04

arrow
Pharma, Lab & Chemical Expo
Not Confirmed
arrow
Pharma, Lab & Chemical Expo
Not Confirmed

MESALAMINE

US Patent Number : 7645801

Drug Substance Claim : Y

Drug Product Claim : Y

Application Number : 19618

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2027-07-24

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