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2D Structure
Also known as: 71125-38-7, Mobic, Metacam, Movalis, Movatec, Mobec
Molecular Formula
C14H13N3O4S2
Molecular Weight
351.4  g/mol
InChI Key
ZRVUJXDFFKFLMG-UHFFFAOYSA-N
FDA UNII
VG2QF83CGL

A benzothiazine and thiazole derivative that acts as a NSAID and cyclooxygenase-2 (COX-2) inhibitor. It is used in the treatment of RHEUMATOID ARTHRITIS; OSTEOARTHRITIS; and ANKYLOSING SPONDYLITIS.
Meloxicam is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of meloxicam is as a Cyclooxygenase Inhibitor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-16,2-benzothiazine-3-carboxamide
2.1.2 InChI
InChI=1S/C14H13N3O4S2/c1-8-7-15-14(22-8)16-13(19)11-12(18)9-5-3-4-6-10(9)23(20,21)17(11)2/h3-7,18H,1-2H3,(H,15,16,19)
2.1.3 InChI Key
ZRVUJXDFFKFLMG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CN=C(S1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)O
2.2 Other Identifiers
2.2.1 UNII
VG2QF83CGL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Masflex

2. Miloxicam

3. Mobec

4. Mobic

5. Mobicox

6. Movalis

7. Movicox

8. Parocin

9. Reumoxicam

10. Uticox

2.3.2 Depositor-Supplied Synonyms

1. 71125-38-7

2. Mobic

3. Metacam

4. Movalis

5. Movatec

6. Mobec

7. Mobicox

8. Meloxicam (mobic)

9. Uh-ac 62xx

10. Meloxivet

11. Coxicam

12. Melfax

13. Parocin

14. Meloxicamum [latin]

15. 4-hydroxy-2-methyl-n-(5-methylthiazol-2-yl)-2h-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide

16. 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

17. Meloxicamum

18. Meloxidolor

19. Melosus

20. Meloxoral

21. Rheumocam

22. Vivlodex

23. Revitacam

24. Acticam

25. Contacera

26. Emdocam

27. Flexicam

28. Inflacam

29. Loxicom

30. Melovem

31. Meloxidyl

32. Recocam

33. Unii-vg2qf83cgl

34. Uhac-62xx

35. Vg2qf83cgl

36. Chembl599

37. Uh-ac-62 Xx

38. 4-hydroxy-2-methyl-n-(5-methyl-2-thiazolyl)-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

39. Mls000028587

40. Chebi:6741

41. N-1539

42. Ncgc00018248-04

43. Meloxicam 100 Microg/ml In Acetonitrile

44. Smr000058994

45. Dsstox_cid_803

46. N1539

47. 2h-1,2-benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-n-(5-methyl-2-thiazolyl)-, 1,1-dioxide

48. 4-hydroxy-2-methyl-n-(5-methyl-2-thiazolyl)-2h-1,2-benzothiazine-3-carboxamide-1,1-dioxide

49. Dsstox_rid_75796

50. Dsstox_gsid_20803

51. 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2h-1$l^{6},2-benzothiazine-3-carboxamide

52. Revmoksikam

53. Coxflam

54. Melonex

55. Tenaron

56. (3e)-3-[hydroxy-[(5-methyl-1,3-thiazol-2-yl)amino]methylidene]-2-methyl-1,1-dioxo-1lambda6,2-benzothiazin-4-one

57. Cas-71125-38-7

58. Ccris 9139

59. Hsdb 7741

60. Meloxicam [usan:usp:inn:ban]

61. Meloxicam,(s)

62. 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1?^{6},2-benzothiazine-3-carboxamide

63. Mfcd00868752

64. Anjeso

65. Mobic (tn)

66. Opera_id_2

67. Qmiiz Odt

68. Spectrum_001633

69. Meloxicam [inn]

70. Meloxicam [jan]

71. Meloxicam [mi]

72. Meloxicam [hsdb]

73. Meloxicam [usan]

74. Spectrum2_000941

75. Spectrum3_000649

76. Spectrum4_000787

77. Spectrum5_001813

78. Meloxicam [vandf]

79. Meloxicam Impurity Standard

80. Meloxicam [mart.]

81. Meloxicam [usp-rs]

82. Meloxicam [who-dd]

83. Schembl3576

84. Meloxicam (jan/usp/inn)

85. Lopac0_000766

86. Schembl33369

87. Bspbio_002257

88. Kbiogr_001234

89. Kbioss_002113

90. Mls001304725

91. Mls001306413

92. Mls006011422

93. Bidd:gt0726

94. Schembl713100

95. Spectrum1504150

96. Spbio_000902

97. Meloxicam [green Book]

98. Gtpl7220

99. Meloxicam [orange Book]

100. Chembl1741042

101. Dtxsid1020803

102. Meloxicam [ep Monograph]

103. Schembl23589638

104. Kbio2_002113

105. Kbio2_004681

106. Kbio2_007249

107. Kbio3_001477

108. Eti-511

109. Meloxicam [usp Monograph]

110. Zeleris Component Meloxicam

111. Hms1922d19

112. Hms2089b18

113. Hms2096i19

114. Hms2234p07

115. Hms2236c09

116. Hms3259h06

117. Hms3372c13

118. Hms3372p18

119. Hms3655k06

120. Hms3713i19

121. Hms3744k09

122. Hms3884g08

123. Zynrelef Component Meloxicam

124. Albb-027268

125. Amy40407

126. Bcp11928

127. Hy-b0261

128. Tox21_111734

129. Tox21_113192

130. Tox21_201689

131. Tox21_302756

132. Bbl029076

133. Bdbm50056998

134. Ccg-39098

135. Hsci1_000045

136. S1734

137. Stk620505

138. Zinc13129998

139. Meloxicam - Cas 71125-38-7

140. Meloxicam Component Of Zeleris

141. Akos000279442

142. Akos026749959

143. Meloxicam Component Of Zynrelef

144. Tox21_111734_1

145. Zinc103620661

146. Ac-1325

147. Db00814

148. Ks-1084

149. Meloxicam [ema Epar Veterinary]

150. Nc00698

151. 2h-1,2-benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-n-(5-methylthiazolyl)-, 1,1-dioxide

152. Smp2_000133

153. Ncgc00018248-01

154. Ncgc00018248-02

155. Ncgc00018248-03

156. Ncgc00018248-05

157. Ncgc00018248-06

158. Ncgc00018248-07

159. Ncgc00018248-08

160. Ncgc00018248-10

161. Ncgc00018248-23

162. Ncgc00018248-25

163. Ncgc00018248-26

164. Ncgc00022924-03

165. Ncgc00022924-04

166. Ncgc00256316-01

167. Ncgc00259238-01

168. Ncgc00263878-02

169. (e)-3-(hydroxy((5-methylthiazol-2-yl)amino)methylene)-2-methyl-2,3-dihydro-4h-benzo[e][1,2]thiazin-4-one 1,1-dioxide

170. 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1lambda6,2-benzothiazine-3-carboxamide

171. Bh164661

172. Smr000718800

173. Db-055490

174. Meloxicam 1.0 Mg/ml In Dimethyl Sulfoxide

175. Ft-0628193

176. M1959

177. Sw219562-1

178. En300-52507

179. C08169

180. D00969

181. F20356

182. Ab00383033-17

183. Ab00383033-18

184. Ab00383033_20

185. 125m387

186. A837087

187. An-668/13244001

188. Q414028

189. Sr-01000003132-10

190. F2173-0387

191. Z1695493323

192. 4-hydroxy-2-methyl-n-(5-methy-2-thiazolyl)-2h-1,2-benzothiazine-3-caboxamide-1,1-dioxide

193. (3z)-2-methyl-3-[[(5-methyl-1,3-thiazol-2-yl)amino]-oxidanyl-methylidene]-1,1-bis(oxidanylidene)-1$l^{6},2-benzothiazin-4-one

194. (3z)-3-[hydroxy-[(5-methyl-2-thiazolyl)amino]methylidene]-2-methyl-1,1-dioxo-1$l^{6},2-benzothiazin-4-one

195. 133687-22-6

196. 4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[e][1,2]thiazine-3-carboxylic Acid (5-methyl-thiazol-2-yl)-amide

197. 4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[e][1,2]thiazine-3-carboxylic Acid (5-methyl-thiazol-2-yl)-amide

198. 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide

199. 4-hydroxy-2-methyl-n-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2h-1lambda6,2-benzothiazine-3-carboxamide

200. 4-hydroxy-2-methyl-n-(5-methyl-2-thiazole)-2h-1,2-benzothiazine-3 -carboxamide 1,1-dioxide

201. 4-hydroxy-2-methyl-n-(5-methylthiazol-2-yl)-2h-benzo[e][1,2]thiazine-3-carboxamide1,1-dioxide

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 351.4 g/mol
Molecular Formula C14H13N3O4S2
XLogP33
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass351.03474825 g/mol
Monoisotopic Mass351.03474825 g/mol
Topological Polar Surface Area136 Ų
Heavy Atom Count23
Formal Charge0
Complexity628
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 4  
Drug NameMeloxicam
Drug LabelMeloxicam, USP an oxicam derivative, is a member of the enolic acid group of non-steroidal anti-inflammatory drugs (NSAIDs). Each tablet contains 7.5 mg or 15 mg meloxicam for oral administration. Meloxicam is chemically designated as 4-hydroxy-2-met...
Active IngredientMeloxicam
Dosage FormTablet
RouteOral
Strength7.5mg; 15mg
Market StatusPrescription
CompanyUnichem; Breckenridge Pharm; Lupin Pharms; Apotex; Aurobindo Pharma; Sun Pharm Inds; Taro; Cipla; Puracap Pharm; Strides Pharma; Glenmark Generics; Teva Pharms; Zydus Pharms Usa; Dr Reddys Labs; Carlsbad; Mylan

2 of 4  
Drug NameMobic
PubMed HealthMeloxicam (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelMeloxicam, an oxicam derivative, is a member of the enolic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each pastel yellow MOBIC tablet contains 7.5 mg or 15 mg meloxicam for oral administration. Each bottle of MOBIC oral suspension c...
Active IngredientMeloxicam
Dosage FormTablet; Suspension
RouteOral
Strength7.5mg/5ml; 7.5mg; 15mg
Market StatusPrescription
CompanyBoehringer Ingelheim

3 of 4  
Drug NameMeloxicam
Drug LabelMeloxicam, USP an oxicam derivative, is a member of the enolic acid group of non-steroidal anti-inflammatory drugs (NSAIDs). Each tablet contains 7.5 mg or 15 mg meloxicam for oral administration. Meloxicam is chemically designated as 4-hydroxy-2-met...
Active IngredientMeloxicam
Dosage FormTablet
RouteOral
Strength7.5mg; 15mg
Market StatusPrescription
CompanyUnichem; Breckenridge Pharm; Lupin Pharms; Apotex; Aurobindo Pharma; Sun Pharm Inds; Taro; Cipla; Puracap Pharm; Strides Pharma; Glenmark Generics; Teva Pharms; Zydus Pharms Usa; Dr Reddys Labs; Carlsbad; Mylan

4 of 4  
Drug NameMobic
PubMed HealthMeloxicam (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelMeloxicam, an oxicam derivative, is a member of the enolic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each pastel yellow MOBIC tablet contains 7.5 mg or 15 mg meloxicam for oral administration. Each bottle of MOBIC oral suspension c...
Active IngredientMeloxicam
Dosage FormTablet; Suspension
RouteOral
Strength7.5mg/5ml; 7.5mg; 15mg
Market StatusPrescription
CompanyBoehringer Ingelheim

4.2 Therapeutic Uses

Thiazines, Thiazoles; Isoenzymes/antagonists & inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


Meloxicam is indicated for relief of the signs and symptoms of osteoarthritis. Use the lowest effective dose for the shortest duration consistent with individual patient treatment goals. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (September 2007). Available from, as of June 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5437


Meloxicam is used for the management of the signs and symptoms of rheumatoid arthritis in adults. In the management of rheumatoid arthritis in adults, NSAIAs may be useful for initial symptomatic treatment; however, NSAIAs do not alter the course of the disease or prevent joint destruction. /Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2161


Meloxicam is used for the management of the signs and symptoms of pauciarticular or polyarticular course juvenile rheumatoid arthritis in children 2 years of age or older. /NOT included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2161


For more Therapeutic Uses (Complete) data for Meloxicam (7 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ WARNING: Cardiovascular Risk NSAIDs may cause an increased risk of serious cardiovascular thrombotic events, myocardial infarction, and stroke, which can be fatal. This risk may increase with duration of use. Patients with cardiovascular disease or risk factors for cardiovascular disease may be at greater risk. Meloxicam is contraindicated for the treatment of peri-operative pain in the setting of coronary artery bypass graft (CABG) surgery.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (Updated: May 2010). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6513e46b-3229-685b-c83b-2209454fae71


/BOXED WARNING/ WARNING: Gastrointestinal Risk: NSAIDs cause an increased risk of serious gastrointestinal adverse events including bleeding, ulceration, and perforation of the stomach or intestines, which can be fatal. These events can occur at any time during use and without warning symptoms. Elderly patients are at greater risk for serious gastrointestinal events.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (Updated: May 2010). Available from, as of April 24, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6513e46b-3229-685b-c83b-2209454fae71


Contraindications: Known hypersensitivity to meloxicam or any ingredient in the formulation. History of urticaria, angioedema, bronchospasm, severe rhinitis, or shock precipitated by aspirin or other NSAIAs. History of aspirin triad (aspirin sensitivity, asthma, and nasal polyps). Treatment of perioperative pain in the setting of coronary artery bypass graft (CABG) surgery.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2162


Selective COX-2 inhibitors have been associated with an increased risk of serious adverse cardiovascular thrombotic events in certain situations. Several prototypical NSAIAs also have been associated with an increased risk of cardiovascular events. Findings from a recent systematic review of controlled observational studies and a meta-analysis of published and unpublished data from randomized studies of these agents suggest that use of celecoxib (dosage exceeding 200 mg daily), diclofenac, or indomethacin is associated with an increased risk of cardiovascular events. The possibility exists that meloxicam and ibuprofen also are associated with increased cardiovascular risk.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2162


For more Drug Warnings (Complete) data for Meloxicam (25 total), please visit the HSDB record page.


4.4 Drug Indication

Meloxicam is indicated for the symptomatic treatment of arthritis and osteoarthritis. In addition, it is indicated for the pauciarticular and polyarticular course of Juvenile Rheumatoid Arthritis (JRA) in patients aged 2 years old or above. Off-label uses include the treatment of dental or post-surgical pain. In addition to the above, meloxicam has also been studied in the treatment of neuropathic pain. Meloxicam, together with the local anesthetic [bupivacaine], is indicated for the production of postsurgical analgesia in adult patients for up to 72 hours following bunionectomy, open inguinal herniorrhaphy or total knee arthroplasty.


FDA Label


* Cattle:

For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs. For use in diarrhoea in combination with oral re-hydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle. For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy. For the relief of post-operative pain following dehorning in calves.

* Pigs:

For the reduction of symptoms of lameness and inflammation in non-infectious locomotor disorders and for adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Horses:

For use in the alleviation of inflammation and relief of pain in both acute and chronic musculo-skeletal disorders. For the relief of pain associated with equine colic.


* Cattle:

For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs. For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle. For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

* Pigs:

For use in noninfectious locomotor disorders to reduce the symptoms of lameness and inflammation. For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitits-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Horses:

For use in the alleviation of inflammation and relief of pain in both acute and chronic musculoskeletal disorders. For the relief of pain associated with equine colic.

* Dogs: :

Alleviation of inflammation and pain in both acute and chronic musculo-skeletal disorders. Reduction of post-operative pain and inflammation following orthopaedic and soft tissue surgery.

* Cats: :

Reduction of post-operative pain after ovariohysterectomy and minor soft tissue surgery.


* Dogs: : alleviation of inflammation and pain in both acute and chronic musculo-skeletal disorders.

To reduce post-operative pain and inflammation following orthopaedic and soft tissue surgery.

* Cats: : to reduce post-operative pain after ovariohysterectomy and minor soft tissue surgery.

Alleviation of mild to moderate post-operative pain and inflammation following surgical procedures in cats, e. g. orthopaedic and soft tissue surgery.

Alleviation of pain and inflammation in acute and chronic musculo-skeletal disorders in cats.

* Cattle: : for use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs.

For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle.

For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

For the relief of post-operative pain following dehorning in calves.

* Pigs: : for use in non-infectious locomotor disorders to reduce the symptoms of lameness and inflammation.

For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

For the relief of post operative pain associated with minor soft tissue such as castration.

* Horses: : alleviation of inflammation and relief of pain in both acute and chronic musculo-skeletal disorders.

For the relief of pain associated with equine colic.


* Dogs:

Alleviation of inflammation and pain in both acute and chronic musculo-skeletal disorders in dogs. To reduce post-operative pain and inflammation following orthopaedic and soft tissue surgery.

* Cats:

Reduction of post-operative pain after ovariohysterectomy and minor soft tissue surgery.

Alleviation of mild to moderate post-operative pain and inflammation following surgical procedures in cats, e. g. orthopaedic and soft tissue surgery.

Alleviation of pain and inflammation in acute and chronic musculo-skeletal disorders in cats.

* Cattle:

For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs. For use in diarrhoea in combination with oral re-hydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle. For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

* Pigs:

For use in non-infectious locomotor disorders to reduce the symptoms of lameness and inflammation. For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy. For the relief of post operative pain associated with minor soft tissue such as castration.

* Horses:

Alleviation of inflammation and relief of pain in both acute and chronic musculo-skeletal disorders in horses. .

For the relief of pain associated with equine colic.


* Cats:

Alleviation of inflammation and pain in chronic musculoskeletal disorders.

* Dogs:

Alleviation of inflammation and pain in both acute and chronic musculoskeletal disorders.


Alleviation of inflammation and relief of pain in both acute and chronic musculo-skeletal disorders in horses.


* Dogs:

- Alleviation of inflammation and pain in both acute and chronic musculoskeletal disorders.

- Reduction of postoperative pain and inflammation following orthopaedic and soft-tissue surgery.

* Cats:

- Reduction of postoperative pain after ovariohysterectomy and minor soft-tissue surgery.

* Cattle:

- For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs.

- For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle.

- For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

* Pigs:

- For use in noninfectious locomotor disorders to reduce the symptoms of lameness and inflammation.

- For the relief of postoperative pain associated with minor soft-tissue surgery such as castration.

- For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Horses:

- For use in the alleviation of inflammation and relief of pain in both acute and chronic musculoskeletal disorders.

- For the relief of pain associated with equine colic.


* Cattle:

- For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs in cattle.

- For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle.

- For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

* Pigs:

- For use in noninfectious locomotor disorders to reduce the symptoms of lameness and inflammation.

- For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Horses:

- For use in the alleviation of inflammation and relief of pain in both acute and chronic musculoskeletal disorders.

- For the relief of pain associated with equine colic.


Dogs:

- Alleviation of inflammation and pain in both acute and chronic musculo-skeletal disorders in dogs.

Cats:

- Alleviation of mild to moderate post-operative pain and inflammation following surgical procedures in cats, e. g. orthopaedic and soft tissue surgery.

- Alleviation of pain and inflammation in chronic musculo-skeletal disorders in cats.

Guinea pigs:

- Alleviation of mild to moderate post-operative pain associated with soft tissue surgery such as male castration.


* Dogs:

Alleviation of inflammation and pain in both acute and chronic musculoskeletal disorders. To reduce postoperative pain and inflammation following orthopaedic and soft-tissue surgery.

* Cats:

Alleviation of inflammation and pain in chronic musculoskeletal disorders in cats. To reduce postoperative pain after ovariohysterectomy and minor soft-tissue surgery.

* Cattle:

For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs in cattle. For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle. For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

* Pigs:

For use in noninfectious locomotor disorders to reduce the symptoms of lameness and inflammation. For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Horses:

For use in the alleviation of inflammation and relief of pain in both acute and chronic musculoskeletal disorders.

For the relief of pain associated with equine colic.


* Oral suspension: :

Dogs:

Alleviation of inflammation and pain in both acute and chronic musculoskeletal disorders.

* Solution for injection: :

Dogs:

Alleviation of inflammation and pain in both acute and chronic musculoskeletal disorders.

Reduction of postoperative pain and inflammation following orthopaedic and soft-tissue surgery.

Cats:

Reduction of postoperative pain after ovariohysterectomy and minor soft-tissue surgery.


* Dogs:

Alleviation of inflammation and pain in both acute and chronic musculoskeletal disorders.

Reduction of post-operative pain and inflammation following orthopaedic and soft-tissue surgery.

* Cats:

Reduction of post-operative pain after ovariohysterectomy and minor soft-tissue surgery.

* Cattle:

For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs in cattle.

For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle.

For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

* Pigs:

For use in non-infectious locomotor disorders to reduce the symptoms of lameness and inflammation.

For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Horses:

For use in the alleviation of inflammation and relief of pain in both acute and chronic musculoskeletal disorders.

For the relief of pain associated with equine colic.


* Cats: :

- Alleviation of mild to moderate post-operative pain and inflammation following surgical procedures, e. g. orthopaedic and soft tissue surgery.

- Alleviation of pain and inflammation in acute and chronic musculo-skeletal disorders.

- Reduction of post-operative pain after ovariohysterectomy and minor soft tissue surgery.

* Cattle: :

- For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs.

- For use in diarrhoea in combination with oral re-hydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle.

- For the relief of post-operative pain following dehorning in calves.

- For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

* Dogs: :

- Alleviation of inflammation and pain in both acute and chronic musculo-skeletal disorders.

- Reduction of post-operative pain and inflammation following orthopaedic and soft tissue surgery.

* Horses: :

- For use in the alleviation of inflammation and relief of pain in both acute and chronic musculo-skeletal disorders.

- For the relief of pain associated with equine colic.

- Alleviation of inflammation and relief of pain in both acute and chronic musculo-skeletal disorders.

* Pigs: :

- For use in non-infectious locomotor disorders to reduce the symptoms of lameness and inflammation.

- For the relief of post-operative pain associated with minor soft tissue surgery such as castration.

- For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Guinea pigs: :

- Alleviation of mild to moderate post-operative pain associated with soft tissues surgery such as male castration.


* Novem 5-mg/ml solution for injection for cattle and pigs: :

Cattle

- For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs in cattle.

- For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle.

- For the relief of postoperative pain following dehorning in calves.

Pigs

- For use in noninfectious locomotor disorders to reduce the symptoms of lameness and inflammation.

- For the relief of postoperative pain associated with minor soft-tissue surgery such as castration.

* Novem 20-mg/ml solution for injection for cattle and pigs: :

Cattle

- For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs in cattle.

- For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle.

- For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

- For the relief of postoperative pain following dehorning in calves.

Pigs

- For use in noninfectious locomotor disorders to reduce the symptoms of lameness and inflammation.

- For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Novem 40 mg/ml solution for injection for cattle: :

- For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs in cattle.

- For use in diarrhoea in combination with oral re-hydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle.

- For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.


Alleviation of inflammation and pain in both acute and chronic musculoskeletal disorders in dogs.


* Cattle:

For use in acute respiratory infection with appropriate antibiotic therapy to reduce clinical signs in cattle. For use in diarrhoea in combination with oral rehydration therapy to reduce clinical signs in calves of over one week of age and young, non-lactating cattle. For adjunctive therapy in the treatment of acute mastitis, in combination with antibiotic therapy.

* Pigs:

For use in noninfectious locomotor disorders to reduce the symptoms of lameness and inflammation. For the relief of postoperative pain associated with minor soft-tissue surgery such as castration. For adjunctive therapy in the treatment of puerperal septicaemia and toxaemia (mastitis-metritis-agalactia syndrome) with appropriate antibiotic therapy.

* Horses:

For use in the alleviation of inflammation and relief of pain in both acute and chronic musculoskeletal disorders. For the relief of pain associated with equine colic.


Alleviation of inflammation and pain in both acute and chronic musculoskeletal disorders.


* Oral suspension: :

Dogs:

Alleviation of inflammation and pain in both acute and chronic musculo-skeletal disorders.

* Solution for injection: :

Dogs:

Alleviation of inflammation and pain in both acute and chronic musculo-skeletal disorders.

Reduction of post-operative pain and inflammation following orthopaedic and soft tissue surgery.

Cats:

Reduction of postoperative pain after ovariohysterectomy and minor soft tissue surgery


5 Pharmacology and Biochemistry
5.1 Pharmacology

Meloxicam is an anti-inflammatory, analgesic analgesic with antipyretic effects in fever. Prostaglandins are substances that contribute to inflammation. This drug also exerts preferential actions against COX-2, which may reduce the possible gastrointestinal effects of this drug. In humans, meloxicam has demonstrated the ability to decrease erythrocyte sedimentation rate(ESR) in patients with rheumatoid arthritis, and to decrease ESR, C-reactive protein (CRP), as well as aquaporin-1 expression. As with other NSAIDS, prolonged use of meloxicum can result in renal or cardiovascular impairment or thrombotic cardiovascular events. A note on gastrointestinal effects As meloxicam preferentially inhibits COX-2, it is thought to cause less gastrointestinal irritation compared to other NSAIDS. Despite this, it still carries a risk of gastric inflammation, bleeding and ulceration. In one study, patients on meloxicam suffered from gastrointestinal symptoms at a rate of 13% compared to 19% of those on [diclofenac]. GI events were found to be less severe in the meloxicam-treated patients.


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.)


Cyclooxygenase 2 Inhibitors

A subclass of cyclooxygenase inhibitors with specificity for CYCLOOXYGENASE-2. (See all compounds classified as Cyclooxygenase 2 Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
MELOXICAM
5.3.2 FDA UNII
VG2QF83CGL
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


QM01AC06


M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AC - Oxicams

M01AC06 - Meloxicam


5.5 Absorption, Distribution and Excretion

Absorption

The absolute bioavailability oral capsules after a dose was 89% in one pharmacokinetic study. Cmax was reached 56 hours after administration of a single dose given after the first meal of the day. The Cmax doubled when the drug was administered in the fasting state. Despite this, meloxicam can be taken without regard to food, unlike many other NSAIDS. Meloxicam formulated for instillation with [bupivacaine] produced varied systemic measures following a single dose of varying strength. In patients undergoing bunionectomy, 1.8 mg of meloxicam produced a Cmax of 26 14 ng/mL, a median Tmax of 18 h, and an AUC of 2079 1631 ng\*h/mL. For a 9 mg dose used in herniorrhaphy, the corresponding values were 225 96 ng/mL, 54 h, and the AUC was not reported. Lastly, a 12 mg dose used in total knee arthroplasty produced values of 275 134 ng/mL, 36 h, and 25,673 17,666 ng\*h/mL.


Route of Elimination

Meloxicam is mainly eliminated through metabolism. Its metabolites are cleared through renal and fecal elimination. Less than <0.25% of a dose is eliminated in the urine as unchanged drug. About 1.6% of the parent drug is excreted in the feces.


Volume of Distribution

The volume of distribution of meloxicam is 10-15L. Because of its high binding to albumin, it is likely to be distributed in highly perfused tissues, such as the liver and kidney. Meloxicam concentrations in synovial fluid, measured after an oral dose, is estimated at 40% to 50% of the concentrations measured in the plasma. This drug is known to cross the placenta in humans.


Clearance

After an oral dose, the total clearance of meloxicam is 0.420.48 L/h. The FDA label indicates a plasma clearance from 7 to 9 mL/min. No dose changes are required in mild to moderate renal or hepatic impairment. The use of meloxicam in patients with severe renal or hepatic impairment has not been studied. FDA prescribing information advises against it.


The absolute bioavailability of meloxicam capsules was 89% following a single oral dose of 30 mg compared with 30 mg iv bolus injection. Following single intravenous doses, dose-proportional pharmacokinetics were shown in the range of 5 mg to 60 mg. After multiple oral doses the pharmacokinetics of meloxicam capsules were dose-proportional over the range of 7.5 mg to 15 mg. Mean Cmax was achieved within four to five hours after a 7.5 mg meloxicam tablet was taken under fasted conditions, indicating a prolonged drug absorption. With multiple dosing, steady state concentrations were reached by Day 5. A second meloxicam concentration peak occurs around 12 to 14 hours post-dose suggesting biliary recycling.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (September 2007). Available from, as of June 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5437


Administration of meloxicam capsules following a high fat breakfast (75 g of fat) resulted in mean peak drug levels (ie, Cmax) being increased by approximately 22% while the extent of absorption (AUC) was unchanged. The time to maximum concentration (Tmax) was achieved between 5 and 6 hours.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (September 2007). Available from, as of June 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5437


The mean volume of distribution (Vss) of meloxicam is approximately 10 L. Meloxicam is about 99.4% bound to human plasma proteins (primarily albumin) within the therapeutic dose range. The fraction of protein binding is independent of drug concentration, over the clinically relevant concentration range, but decreases to about 99% in patients with renal disease.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (September 2007). Available from, as of June 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5437


Meloxicam penetration into human red blood cells, after oral dosing, is less than 10%. Following a radiolabeled dose, over 90% of the radioactivity detected in the plasma was present as unchanged meloxicam.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (September 2007). Available from, as of June 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5437


For more Absorption, Distribution and Excretion (Complete) data for Meloxicam (14 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Meloxicam is almost completely metabolized. CYP2C9 is the main enzyme responsible for the metabolism of meloxicam with minor contributions from CYP3A4. Meloxicam has 4 major metabolites with no activity determined. About 60% of the ingested dose is metabolized to 5'-carboxy meloxicam from hepatic cytochrome enzyme oxidation of an intermediate metabolite, 5-hydroxymethylmeloxicam. Two other metabolites are likely produced via peroxidation.


Meloxicam is almost completely metabolized to four pharmacologically inactive metabolites. The major metabolite, 5'-carboxy meloxicam (60% of dose), from P-450 mediated metabolism was formed by oxidation of an intermediate metabolite 5'-hydroxymethyl meloxicam which is also excreted to a lesser extent (9% of dose). In vitro studies indicate that cytochrome P-450 2C9 plays an important role in this metabolic pathway with a minor contribution of the CYP 3A4 isozyme.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (September 2007). Available from, as of June 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5437


Patients' peroxidase activity is probably responsible for /two other/ metabolites which account for 16% and 4% of the administered dose, respectively.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (September 2007). Available from, as of June 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5437


Meloxicam is extensively metabolized to inactive metabolites in the liver, principally via the cytochrome P-450 (CYP) 2C9 isoenzyme, with minor contribution by CYP3A4. The drug and its metabolites are excreted in urine and feces, and meloxicam undergoes substantial biliary secretion and enterohepatic recirculation.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2163


The metabolism of Meloxicam (ME) and the cytochrome(s) P450 (CYPs) involved were analysed by using primary human hepatocytes, human liver microsomes and microsomes from recombinant human B-lymphoblastoid cell lines. While human hepatocytes were capable of converting ME to a 5-hydroxymethyl metabolite (M7) and then to a 5-carboxyderivative (M5), human liver microsomes formed mostly only the 5-hydroxymethylderivative. The kinetics of the formation of M7 by human liver microsomes were biphasic with Km = 13.6 +/- 9.5 and 381 +/- 55.2 uM respectively. The corresponding Vmax were 33.7 +/- 24.2 and 143 +/- 83.9 pmol/min/mg protein respectively. CYP2C9 and, to a much lesser extent, CYP3A4 were found to convert ME to M7. The involvement of 2C9 was demonstrated by inhibition of tolbutamide hydroxylase activity in the presence of ME, inhibition of ME metabolism by sulphaphenazole, correlation between ME metabolism and tolbutamide hydroxylase activity and active metabolism of ME by recombinant 2C9. The involvement of 3A4 was shown by inhibition of ME metabolism by ketoconazole, correlation between ME metabolism and nifedipine oxidase activity and metabolism of ME by recombinant 3A4. Kinetics of the formation of M7 by the individual enzymes resulted in a Km = 9.6 uM and Vmax = 8.4 pmol/min/mg protein for 2C9 and a Km = 475 uM and Vmax = 23 pmol/min/mg protein for 3A4.

PMID:9493314 Chesne C et al; Xenobiotica 28 (1): 1-13 (1998).


For more Metabolism/Metabolites (Complete) data for Meloxicam (6 total), please visit the HSDB record page.


Meloxicam has known human metabolites that include 5-Hydroxymethyl meloxicam.

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


5.7 Biological Half-Life

The half-life of meloxicam is approximately 20 hours, which is considerably longer than most other NSAIDS. It can therefore be dosed without the need for slow-release formulations. Meloxicam applied together with [bupivacaine] for postsurgical analgesia had a median half-life of 33-42 hours, depending on dose and application site.


The mean elimination half-life (t1/2) ranges from 15 hours to 20 hours. The elimination half-life is constant across dose levels indicating linear metabolism within the therapeutic dose range.

US Natl Inst Health; DailyMed. Current Medication Information for Meloxicam (meloxicam) tablets (September 2007). Available from, as of June 29, 2009: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5437


... The twenty volunteers can be classified into extensive metabolizers and poor metabolizers according to pharmacokinetic parameters. The main parameters in the two groups obtained were as follows: T 1/2 were 21 +/- 4 and 38 +/- 9 hr, respectively. ...

PMID:12579866 Xu HY et al; Yao Xue Xue Bao 36 (1): 71-3 (2001).


5.8 Mechanism of Action

Meloxicam inhibits prostaglandin synthetase (cylooxygenase 1 and 2) enzymes leading to a decreased synthesis of prostaglandins, which normally mediate painful inflammatory symptoms. As prostaglandins sensitize neuronal pain receptors, inhibition of their synthesis leads to analgesic and inflammatory effects. Meloxicam preferentially inhibits COX-2, but also exerts some activity against COX-1, causing gastrointestinal irritation.


Meloxicam, an oxicam derivative that is structurally related to piroxicam, is a nonsteroidal anti-inflammatory agent (NSAIA) exhibiting analgesic, antipyretic, and anti-inflammatory actions. In vitro and in vivo studies indicate that meloxicam inhibits the cyclooxygenase-2 (COX-2) isoform of prostaglandin endoperoxide synthase (prostaglandin G/H synthase [PGHS]) to a greater extent than the COX-1 isoform. However, meloxicam's COX-2 selectivity is dose dependent and is diminished at higher dosages. Therefore meloxicam sometimes has been referred to as a "preferential" rather than "selective" COX-2 inhibitor.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 2162


To investigate the effect of meloxicam on human polymorphonuclear leukocyte (PMN) adhesion to human synovial cell (HSC), and to explore its mechanism. MTT colorimetry was used to determine the adhesion effect of PMN to HSC. Cell-ELISA and RT-PCR methods were used to determine the expression of ICAM-1 and VCAM-1. Nuclear transcription factor-kappa B (NF-kappa B) was measured by electrophoretic mobility shift assay (EMSA) method. Meloxicam was found to effectively inhibit TNF-alpha (50 u.mL-1 for 12 hr) and IL-1 beta (50 u.mL-1 for 12 hr)-induced adhesion of PMN to HSC (IC50 3.38 X 10(-7) mol.L-1 and 3.56 X 10(-6) mol.L-1, respectively) in a concentration-dependent manner. ICAM-1 protein and mRNA expression induced by TNF-alpha (50 u.mL-1) were inhibited by meloxicam at 1 X 10(-6)-1 X 10(-5) mol.L-1. The activation of NF-kappa B was also inhibited by meloxicam at 1 X 10(-6)-1 X 10(-5) mol.L-1. These results suggest that meloxicam inhibit TNF-alpha stimulated PMN-HSC adhesion and expression of ICAM-1 by suppressing the activity of NF-kappa B.

PMID:12579952 Li LC et al; Yao Xue Xue Bao 37 (2): 103-7 (2002).


/Investigators/ compared the effects of therapeutically equivalent doses of meloxicam and indomethacin, a preferential inhibitor of the constitutive cyclooxygenase (COX-1), on platelet aggregation and platelet thromboxane formation, which are exclusively COX-1 dependent, physiological renal, and total body prostaglandin E2 (PGE2) production. In a randomized cross-over design, 14 healthy female volunteers received meloxicam 7.5 mg per day for 6 days or indomethacin 25 mg three times per day for 3 days; the wash-out period was 5 days, and drug intake was adapted to the menstrual cycle. On the day before treatment and on the last day of each treatment period the following parameters were evaluated: maximum platelet aggregation and thromboxane B2 (TXB2) formation in response to 1.0 mmol/L arachidonic acid; 24-hour urinary excretion of PGE2 and 7 alpha-hydroxy-5, 11-diketo-tetranor-prosta-1, 16-dionic acid (PGE-M), the index metabolites of renal and total body PGE2 synthesis, respectively, were assessed by gas chromatography/tandem mass spectrometry. Maximum platelet aggregation and TXB2 formation were almost completely inhibited by indomethacin (-87% and -99%, respectively; p < 0.001, each) as compared to control (100%), but remained unaffected by meloxicam (-1% and +4%, respectively). Meloxicam showed no significant effects on urinary PGE2 excretion (-13%) and only slight effects on PGE-M excretion (-22%; p < 0.05), whereas indomethacin reduced urinary PGE2 excretion (-43%; p < 0.05) as well as PGE-M excretion (-36%; p < 0.001). /This/ data shows, that meloxicam 7.5 mg per day is COX-1 sparing in humans in vivo.

PMID:9084574 Stichtenoth DO et al; J Investig Med 45 (2): 44-9 (1997).