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Prestwick3_000211
Also known as: 36322-90-4, Feldene, Piroxicamum, Pyroxycam, Roxicam, Piroftal
Molecular Formula
C15H13N3O4S
Molecular Weight
331.3  g/mol
InChI Key
QYSPLQLAKJAUJT-UHFFFAOYSA-N
FDA UNII
13T4O6VMAM

A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily.
Piroxicam is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of piroxicam is as a Cyclooxygenase Inhibitor.
1 2D Structure

Prestwick3_000211

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-yl-16,2-benzothiazine-3-carboxamide
2.1.2 InChI
InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
2.1.3 InChI Key
QYSPLQLAKJAUJT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1C(=C(C2=CC=CC=C2S1(=O)=O)O)C(=O)NC3=CC=CC=N3
2.2 Other Identifiers
2.2.1 UNII
13T4O6VMAM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cp 16171

2. Cp-16171

3. Cp16171

4. Feldene

2.3.2 Depositor-Supplied Synonyms

1. 36322-90-4

2. Feldene

3. Piroxicamum

4. Pyroxycam

5. Roxicam

6. Piroftal

7. Baxo

8. Cp-16171

9. 2h-1,2-benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-n-2-pyridinyl-, 1,1-dioxide

10. 4-hydroxy-2-methyl-n-(pyridin-2-yl)-2h-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide

11. Cp 16171

12. Chf 1251

13. Nsc 666076

14. Piroxicam (feldene)

15. 4-hydroxy-2-methyl-n-(2-pyridyl)-2h-1,2-benzothiazine-3-carboxamide-1,1-dioxide

16. Nsc-666076

17. 13t4o6vmam

18. 4-hydroxy-2-methyl-3-(pyrid-2-yl-carbamoyl)-2h-1,2-benzothiazine 1,1-dioxide

19. 4-hydroxy-2-methyl-n-(2-pyridyl)-2h-1,2-benzothiazin-3-caboxyamid-1,1-dioxid

20. 4-hydroxy-2-methyl-n-2-pyridyl-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

21. Cp-16,171

22. Mls000069644

23. Chebi:8249

24. Nsc666076

25. 4-hydroxy-2-methyl-n-pyridin-2-yl-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

26. Ncgc00015823-02

27. Artroxicam

28. Bruxicam

29. Caliment

30. Flogobene

31. Geldene

32. Improntal

33. Larapam

34. Piroflex

35. Reudene

36. Roxiden

37. Sasulen

38. Smr000035997

39. Solocalm

40. Erazon

41. Pirkam

42. Piroxicam Usp

43. Riacen

44. Zunden

45. Roxam

46. Cas-36322-90-4

47. Dsstox_cid_1170

48. 4-hydroxy-2-methyl-1,1-dioxo-n-pyridin-2-yl-1lambda6,2-benzothiazine-3-carboxamide

49. 4-hydroxy-2-methyl-n-2-pyridinyl-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

50. Dsstox_rid_75990

51. Dsstox_gsid_21170

52. Piroxicamum [inn-latin]

53. Piroxicam D3 (n-methyl D3)

54. Rosiden

55. Felden

56. Feldene Fast

57. Feldene Gel

58. 4-hydroxy-2-methyl-n-(2-pyridyl)-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

59. 4-hydroxy-2-methyl-n-2-pyridinyl-2h-1,2-benzothiazine-3-carboxamide-1,1-dioxide

60. (z)-3-(hydroxy(pyridin-2-ylamino)methylene)-2-methyl-2h-benzo[e][1,2]thiazin-4(3h)-one 1,1-dioxide

61. Feldene (tn)

62. Ccris 3719

63. Sr-01000000199

64. Einecs 252-974-3

65. Ak1015

66. Unii-13t4o6vmam

67. Brn 0627692

68. 4-hydroxy-2-methyl-1,1-dioxo-n-pyridin-2-yl-1?^{6},2-benzothiazine-3-carboxamide

69. Piroxicam,(s)

70. Prestwick_573

71. Mfcd00057317

72. 4-hydroxy-2-methyl-n-(2-pyridyl)-2h-1,2-benzothiazin-3-caboxyamid-1,1-dioxid [german]

73. Piroxicam [usan:usp:inn:ban:jan]

74. Piroxicam:malonic Acid

75. Spectrum_001115

76. Tocris-0960

77. Piroxicam-(methyl-d3)

78. Opera_id_442

79. Piroxicam [inn]

80. Piroxicam [jan]

81. Piroxicam: Form Alpha1

82. Piroxicam: Form Alpha2

83. Piroxicam [mi]

84. Piroxicam [usan]

85. Prestwick0_000211

86. Prestwick1_000211

87. Prestwick2_000211

88. Prestwick3_000211

89. Spectrum2_001287

90. Spectrum3_000780

91. Spectrum4_000968

92. Spectrum5_001445

93. Lopac-p-5654

94. Piroxicam [vandf]

95. Piroxicam Anhydrous

96. Chembl527

97. Piroxicam [mart.]

98. P 5654

99. Piroxicam [usp-rs]

100. Piroxicam [who-dd]

101. Bidd:pxr0154

102. Lopac0_000900

103. Oprea1_714707

104. Schembl13462

105. Schembl21350

106. Bspbio_000221

107. Bspbio_001030

108. Bspbio_002460

109. Kbiogr_000370

110. Kbiogr_001315

111. Kbioss_000370

112. Kbioss_001595

113. Mls000038002

114. Mls001148207

115. Mls001304054

116. Mls004774122

117. Divk1c_000369

118. Spectrum1500491

119. Spbio_001293

120. Spbio_002142

121. Piroxicam (jp17/usp/inn)

122. Bpbio1_000245

123. Gtpl7273

124. Piroxicam, >=98% (tlc)

125. Schembl3703617

126. Piroxicam [orange Book]

127. Piroxicam For System Suitability

128. Chembl1518938

129. Dtxsid5021170

130. Piroxicam [ep Monograph]

131. Bcbcmap01_000176

132. Bdbm85245

133. Hms501c11

134. Kbio1_000369

135. Kbio2_000370

136. Kbio2_001595

137. Kbio2_002938

138. Kbio2_004163

139. Kbio2_005506

140. Kbio2_006731

141. Kbio3_000719

142. Kbio3_000720

143. Kbio3_001680

144. Piroxicam [usp Monograph]

145. Ninds_000369

146. Piroxicam 1.0 Mg/ml In Methanol

147. Bio1_000363

148. Bio1_000852

149. Bio1_001341

150. Bio2_000355

151. Bio2_000835

152. Glxc-26155

153. Glxc-26156

154. Hms1362d11

155. Hms1568l03

156. Hms1792d11

157. Hms1920h22

158. Hms1990d11

159. Hms2089b06

160. Hms2092a05

161. Hms2095l03

162. Hms2231g03

163. Hms3262d22

164. Hms3267i03

165. Hms3369b07

166. Hms3403d11

167. Hms3414h17

168. Hms3429l03

169. Hms3655c04

170. Hms3678h15

171. Hms3712l03

172. Hms3884c08

173. Pharmakon1600-01500491

174. Bcp02919

175. Hy-b0253

176. Nsc_4856

177. Tox21_110231

178. Tox21_200151

179. Tox21_500900

180. Ccg-36403

181. Nsc757284

182. S1713

183. Stk177288

184. Zinc12466469

185. Zinc51133897

186. Zinc87724780

187. Akos000714958

188. Akos025312555

189. Akos026749939

190. Tox21_110231_1

191. Am84917

192. Db00554

193. Ks-5322

194. Lp00900

195. Nsc-757284

196. Sdccgsbi-0050875.p005

197. (4-hydroxy-2-methyl-1,1-dioxobenzo[e]1,2-thiazin-3-yl)-n-(2-pyridyl)carboxamid E

198. (4-hydroxy-2-methyl-1,1-dioxobenzo[e]1,2-thiazin-3-yl)-n-(2-pyridyl)carboxamide

199. 2h-1,2-benzothiazine-3-carboxamide,4-hydroxy-2-methyl-n-2-pyridinyl-, 1,1-dioxide

200. 3,4-dihydro-2-methyl-4-oxo-n-2-pyridyl-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

201. 4-hydroxy-2-methyl-n-(pyridin-2-yl)-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

202. Idi1_000369

203. Idi1_002110

204. Ncgc00015823-01

205. Ncgc00015823-03

206. Ncgc00015823-04

207. Ncgc00015823-05

208. Ncgc00015823-06

209. Ncgc00015823-07

210. Ncgc00015823-08

211. Ncgc00015823-09

212. Ncgc00015823-10

213. Ncgc00015823-11

214. Ncgc00015823-12

215. Ncgc00015823-13

216. Ncgc00015823-14

217. Ncgc00015823-15

218. Ncgc00015823-17

219. Ncgc00015823-18

220. Ncgc00015823-20

221. Ncgc00015823-29

222. Ncgc00021244-03

223. Ncgc00021244-05

224. Ncgc00021244-06

225. Ncgc00021244-07

226. Ncgc00021244-08

227. Ncgc00021244-09

228. Ncgc00188982-01

229. Ncgc00257705-01

230. Ncgc00261585-01

231. Piroxicam 100 Microg/ml In Acetonitrile

232. 1488516-58-0

233. Ac-24190

234. Nci60_022912

235. Bcp0726000299

236. Sbi-0050875.p004

237. Cas_36322-90-4

238. Piroxicam, Meets Usp Testing Specifications

239. Eu-0100900

240. Ft-0630590

241. Ft-0673949

242. P1905

243. Sw219862-1

244. En300-70724

245. A19556

246. C01608

247. D00127

248. D70554

249. Ab00052074-21

250. Ab00052074-22

251. Ab00052074_23

252. Ab00052074_24

253. 322p904

254. Q408676

255. Sr-01000000199-3

256. Sr-01000000199-5

257. Sr-01000000199-9

258. W-106626

259. Sr-01000000199-12

260. F0001-2399

261. Piroxicam, British Pharmacopoeia (bp) Reference Standard

262. Z1259192069

263. Piroxicam, European Pharmacopoeia (ep) Reference Standard

264. Piroxicam, United States Pharmacopeia (usp) Reference Standard

265. Piroxicam, Pharmaceutical Secondary Standard; Certified Reference Material

266. 4-hydroxy-2-methyl-1,1-dioxo-n-(2-pyridyl)-1$l^{6},2-benzothiazine-3-carboxamide

267. 4-hydroxy-2-methyl-1,1-dioxo-n-(pyridin-2-yl)-2h-1$l^{6},2-benzothiazine-3-carboxamide

268. 4-hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2h-1,2-benzothiazine 1,1-dioxide

269. 4-hydroxy-2-methyl-n-(2-pyridyl)-2h-1,2-benzo-thiazine-3-carboxamide1,1-dioxide

270. 4-hydroxy-2-methyl-n-(pyridin-2-yl)-2h-benzo[e][1,2]thiazine-3-carboxamide1,1-dioxide

271. 4-hydroxy-2-methyl-n-2-pyridinyl-2h-1,2-benzothiazine-3-carboxamide1,1-dioxide

272. N-(2-pyridyl)-4-hydroxy-2-methyl-2h-1,2-benzothiazine-3-carboxamide 1,1-dioxide

273. 1044566-76-8

274. 3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-3,4-dihydro-2h-1$l^{6},2-benzothiazine-1,1,4-trione

275. 3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-3,4-dihydro-2h-1lambda6,2-benzothiazine-1,1,4-trione

276. 4-hydroxy-2-methyl-1,1-dioxo-n-(2-pyridyl)-1,2-dihydro-1lambda,2-benzothiazine-3-carboxamide

277. 4-hydroxy-2-methyl-n-(2-pyridyl)-2h-1,2-benzothiazine -3-carboxamide-1,1-dioxide Malonic Acid

2.4 Create Date
2011-12-26
3 Chemical and Physical Properties
Molecular Weight 331.3 g/mol
Molecular Formula C15H13N3O4S
XLogP33.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass331.06267708 g/mol
Monoisotopic Mass331.06267708 g/mol
Topological Polar Surface Area108 Ų
Heavy Atom Count23
Formal Charge0
Complexity611
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 6  
Drug NameAkten
PubMed HealthLidocaine (Into the eye)
Drug ClassesAnesthetic, Local
Active IngredientLidocaine hydrochloride
Dosage FormGel
RouteOphthalmic
Strength3.5%
Market StatusPrescription
CompanyAkorn

2 of 6  
Drug NameFeldene
PubMed HealthPiroxicam (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelFELDENEcontains piroxicam which is a member of the oxicam group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each maroon and blue capsule contains 10 mg piroxicam, each maroon capsule contains 20 mg piroxicam for oral administration. The chemica...
Active IngredientPiroxicam
Dosage FormCapsule
RouteOral
Strength10mg; 20mg
Market StatusPrescription
CompanyPfizer

3 of 6  
Drug NamePiroxicam
PubMed HealthPiroxicam (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelPiroxicam capsules USP contain piroxicam which is a member of the oxicam group of non-steroidal anti-inflammatory drugs (NSAIDs). Each dark green and olive capsule contains 10 mg piroxicam, each dark green capsule contains 20 mg piroxicam for oral ad...
Active IngredientPiroxicam
Dosage FormCapsule
RouteOral
Strength10mg; 20mg
Market StatusPrescription
CompanyTeva; Nostrum Labs; Mutual Pharm; Mylan

4 of 6  
Drug NameAkten
PubMed HealthLidocaine (Into the eye)
Drug ClassesAnesthetic, Local
Active IngredientLidocaine hydrochloride
Dosage FormGel
RouteOphthalmic
Strength3.5%
Market StatusPrescription
CompanyAkorn

5 of 6  
Drug NameFeldene
PubMed HealthPiroxicam (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelFELDENEcontains piroxicam which is a member of the oxicam group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each maroon and blue capsule contains 10 mg piroxicam, each maroon capsule contains 20 mg piroxicam for oral administration. The chemica...
Active IngredientPiroxicam
Dosage FormCapsule
RouteOral
Strength10mg; 20mg
Market StatusPrescription
CompanyPfizer

6 of 6  
Drug NamePiroxicam
PubMed HealthPiroxicam (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelPiroxicam capsules USP contain piroxicam which is a member of the oxicam group of non-steroidal anti-inflammatory drugs (NSAIDs). Each dark green and olive capsule contains 10 mg piroxicam, each dark green capsule contains 20 mg piroxicam for oral ad...
Active IngredientPiroxicam
Dosage FormCapsule
RouteOral
Strength10mg; 20mg
Market StatusPrescription
CompanyTeva; Nostrum Labs; Mutual Pharm; Mylan

4.2 Drug Indication

For treatment of osteoarthritis and rheumatoid arthritis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Piroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). Piroxicam works by reducing hormones that cause inflammation and pain in the body. Piroxicam is used to reduce the pain, inflammation, and stiffness caused by rheumatoid arthritis and osteoarthritis.


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 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PIROXICAM
5.3.2 FDA UNII
13T4O6VMAM
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

M01AC01

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


M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AC - Oxicams

M01AC01 - Piroxicam


M - Musculo-skeletal system

M02 - Topical products for joint and muscular pain

M02A - Topical products for joint and muscular pain

M02AA - Antiinflammatory preparations, non-steroids for topical use

M02AA07 - Piroxicam


S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BC - Antiinflammatory agents, non-steroids

S01BC06 - Piroxicam


5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed following oral administration.


Route of Elimination

Piroxicam and its biotransformation products are excreted in urine and feces, with about twice as much appearing in the urine as in the feces. Approximately 5% of a piroxicam dose is excreted unchanged. However, a substantial portion of piroxicam elimination occurs by hepatic metabolism. Piroxicam is excreted into human milk.


Volume of Distribution

0.14 L/kg


5.6 Metabolism/Metabolites

Renal


Piroxicam has known human metabolites that include 5'-Hydroxypiroxicam.

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


5.7 Biological Half-Life

30 to 86 hours


5.8 Mechanism of Action

The antiinflammatory effect of Piroxicam may result from the reversible inhibition of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. The prostaglandins are produced by an enzyme called Cox-1. Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets.


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  • CAPSULE;ORAL - 10MG
  • CAPSULE;ORAL - 20MG
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