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Chemistry

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Also known as: 41340-25-4, Etodolic acid, Lodine, Ultradol, Lodine xl, Ay-24236
Molecular Formula
C17H21NO3
Molecular Weight
287.35  g/mol
InChI Key
NNYBQONXHNTVIJ-UHFFFAOYSA-N
FDA UNII
2M36281008

Etodolac
A non-steroidal anti-inflammatory agent and cyclooxygenase-2 (COX-2) inhibitor with potent analgesic and anti-arthritic properties. It has been shown to be effective in the treatment of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; ANKYLOSING SPONDYLITIS; and in the alleviation of postoperative pain (PAIN, POSTOPERATIVE).
Etodolac is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of etodolac is as a Cyclooxygenase Inhibitor.
1 2D Structure

Etodolac

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(1,8-diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetic acid
2.1.2 InChI
InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)
2.1.3 InChI Key
NNYBQONXHNTVIJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC1=C2C(=CC=C1)C3=C(N2)C(OCC3)(CC)CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
2M36281008
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ay 24,236

2. Ay 24236

3. Ay-24,236

4. Ay-24236

5. Etodolac, (+-)-isomer

6. Etodolac, (-)-isomer

7. Etodolac, (s)-isomer

8. Etodolac, Monosodium Salt

9. Etodolac, Monosodium Salt, (+-) Isomer

10. Etodolac, Monosodium Salt, (s)-isomer

11. Etodolic Acid

12. Lodine

13. Ramodar

14. Ultradol

2.3.2 Depositor-Supplied Synonyms

1. 41340-25-4

2. Etodolic Acid

3. Lodine

4. Ultradol

5. Lodine Xl

6. Ay-24236

7. Edolan

8. Ramodar

9. Ay-24,236

10. Etodolaco

11. Etodolacum

12. Tedolan

13. Zedolac

14. Rac-etodolac

15. Ay 24236

16. Eccoxolac

17. Flancox

18. Napilac

19. 2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic Acid

20. Lodin Xl

21. 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic Acid

22. Pyrano[3,4-b]indole-1-acetic Acid, 1,8-diethyl-1,3,4,9-tetrahydro-

23. (rs)-etodolic Acid

24. 1,3,4,9-tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic Acid

25. 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic Acid

26. 2-(1,8-diethyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)acetic Acid

27. Chembl622

28. Nsc-282126

29. (1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic Acid

30. Pyrano(3,4-b)indole-1-acetic Acid, 1,8-diethyl-1,3,4,9-tetrahydro-

31. Mls000028474

32. Chebi:4909

33. Rak-591

34. 2-{1,8-diethyl-1h,3h,4h,9h-pyrano[3,4-b]indol-1-yl}acetic Acid

35. (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic Acid

36. Nih-9918

37. Nsc282126

38. Smr000058443

39. Ay-24-236

40. Dsstox_cid_615

41. (+-)-1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic Acid

42. (rs)-2-(1,8-diethyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)acetic Acid

43. Etodolacum [inn-latin]

44. Dsstox_rid_75691

45. Dsstox_gsid_20615

46. Etodolaco [inn-spanish]

47. 2m36281008

48. Hypen

49. 1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indole-1-acetic Acid

50. 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetic Acid

51. (+/-)-1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic Acid

52. Ccris 3923

53. Sr-01000000100

54. Nsc 282126

55. Etogesic

56. Osteluc

57. Etodolac O

58. Etodlic Acid

59. Lodine Sr

60. Etodolac [usan:usp:inn:ban]

61. Etodolac- Bio-x

62. Ncgc00016849-01

63. Etodolac,(s)

64. Prestwick_209

65. Cas-41340-25-4

66. Lodine (tn)

67. Mfcd00133313

68. Unii-2m36281008

69. Etodolac Assay Standard

70. Spectrum_001244

71. Etodolac [usan]

72. Etodolac [inn]

73. Etodolac [jan]

74. Etodolac [mi]

75. Etodolac [vandf]

76. Opera_id_1774

77. Prestwick0_000231

78. Prestwick1_000231

79. Prestwick2_000231

80. Prestwick3_000231

81. Spectrum2_001387

82. Spectrum3_001429

83. Spectrum4_000410

84. Spectrum5_001347

85. Etodolac [mart.]

86. Etodolac [usp-rs]

87. Etodolac [who-dd]

88. Schembl3903

89. Lopac0_000479

90. (+/-)-etodolac

91. Bspbio_000301

92. Bspbio_003138

93. Kbiogr_000680

94. Kbioss_001724

95. Mls001077315

96. Mls006011566

97. Divk1c_000147

98. Etodolac [green Book]

99. Spectrum1501005

100. Etodolac (jp17/usp/inn)

101. Spbio_001374

102. Spbio_002222

103. Etodolac [orange Book]

104. Bpbio1_000333

105. Gtpl7185

106. Etodolac [ep Monograph]

107. Etodolac For Peak Identification

108. Dtxsid9020615

109. Etodolac [usp Monograph]

110. Hms500h09

111. Kbio1_000147

112. Kbio2_001724

113. Kbio2_004292

114. Kbio2_006860

115. Kbio3_002358

116. Ninds_000147

117. Hms1568p03

118. Hms1921b09

119. Hms2092o20

120. Hms2095p03

121. Hms2231d04

122. Hms3259p10

123. Hms3261o20

124. Hms3374g09

125. Hms3712p03

126. Pharmakon1600-01501005

127. Bcp28411

128. Tox21_110644

129. Tox21_202218

130. Tox21_500479

131. Bdbm50016799

132. Ccg-39005

133. Nsc757821

134. Pyrano(3,4-b)indole-1-acetic Acid, 1,3,4,9-tetrahydro-1,8-diethyl-

135. Akos015838610

136. Pyrano(3,4-b)indole-1-acetic Acid, 1,8-diethyl-1,3,4,9-tetrahydro-(+-)-

137. Tox21_110644_1

138. Ac-4231

139. Cs-0832

140. Db00749

141. Lp00479

142. Nc00718

143. Nsc-757821

144. Sdccgsbi-0050463.p004

145. Etodolac 100 Microg/ml In Acetonitrile

146. Idi1_000147

147. Ncgc00015399-03

148. Ncgc00015399-04

149. Ncgc00015399-05

150. Ncgc00015399-06

151. Ncgc00015399-07

152. Ncgc00015399-08

153. Ncgc00015399-09

154. Ncgc00015399-11

155. Ncgc00015399-12

156. Ncgc00015399-13

157. Ncgc00015399-15

158. Ncgc00015399-16

159. Ncgc00015399-26

160. Ncgc00089769-02

161. Ncgc00089769-03

162. Ncgc00089769-04

163. Ncgc00089769-05

164. Ncgc00089769-06

165. Ncgc00089769-07

166. Ncgc00259767-01

167. Ncgc00261164-01

168. Br164431

169. Hy-76251

170. Sbi-0050463.p003

171. Ab00052194

172. E0858

173. Eu-0100479

174. Ft-0607046

175. Ft-0668424

176. Ft-0668425

177. C06991

178. D00315

179. E 0516

180. Pyrano[3, 1,8-diethyl-1,3,4,9-tetrahydro-

181. Ab00052194_17

182. 340e254

183. Q-201099

184. Q2465218

185. Sr-01000000100-2

186. Sr-01000000100-4

187. Sr-01000000100-7

188. Brd-a74667430-001-05-3

189. Brd-a74667430-001-15-2

190. 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic Acid

191. Etodolac, European Pharmacopoeia (ep) Reference Standard

192. F2173-0681

193. Z1820178466

194. Etodolac, United States Pharmacopeia (usp) Reference Standard

195. 1,8-diethyl-1,3,4,9-tetrahydropyranol[3,4-b]indole-1-acetic Acid

196. 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indol-1-acetic Acid

197. 2-(1,8-diethyl-4,9-dihydro-3h-pyrano[3,4-b]indol-1-yl)acetic Acid.

198. Pyrano(3,4,b)indole-1-acetic Acid, 1,3,4,9-tetrahydro-1,8-diethyl-

199. Ay 24,236; Ay 24236;ay-24,236; Ay-24236; Ay24,236; Ay24236

200. Etodolac For Peak Identification, European Pharmacopoeia (ep) Reference Standard

201. Pyrano(3,4-b)indole-1-acetic Acid, 1,8-diethyl-1,3,4,9-tetrahydro-(+/-)-

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 287.35 g/mol
Molecular Formula C17H21NO3
XLogP32.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass287.15214353 g/mol
Monoisotopic Mass287.15214353 g/mol
Topological Polar Surface Area62.3 Ų
Heavy Atom Count21
Formal Charge0
Complexity400
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameEtodolac
PubMed HealthEtodolac (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelEtodolac capsules and tablets, USP are members of the pyranocarboxylic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each tablet and capsule contains etodolac for oral administration. Etodolac is a racemic mixture of [+]S and [-]R-enan...
Active IngredientEtodolac
Dosage FormTablet, extended release; Tablet; Capsule
RouteOral
Strength300mg; 200mg; 600mg; 500mg; 400mg
Market StatusPrescription
CompanyAni Pharms; Teva; Apotex; Taro; Taro Pharm Inds; Zydus Pharms Usa; Sandoz; Mylan

2 of 2  
Drug NameEtodolac
PubMed HealthEtodolac (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelEtodolac capsules and tablets, USP are members of the pyranocarboxylic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). Each tablet and capsule contains etodolac for oral administration. Etodolac is a racemic mixture of [+]S and [-]R-enan...
Active IngredientEtodolac
Dosage FormTablet, extended release; Tablet; Capsule
RouteOral
Strength300mg; 200mg; 600mg; 500mg; 400mg
Market StatusPrescription
CompanyAni Pharms; Teva; Apotex; Taro; Taro Pharm Inds; Zydus Pharms Usa; Sandoz; Mylan

4.2 Drug Indication

For acute and long-term management of signs and symptoms of osteoarthritis and rheumatoid arthritis, as well as for the management of pain.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Etodolac is an anti-inflammatory agent with analgesic and antipyretic properties. It is used to treat osteoarthritis, rheumatoid arthritis and control acute pain. The therapeutic effects of etodolac are achieved via inhibition of the synthesis of prostaglandins involved in fever, pain, swelling and inflammation. Etodolac is administered as a racemate. As with other NSAIDs, the S-form has been shown to be active while the R-form is inactive. Both enantiomers are stable and there is no evidence of R- to S- conversion _in vivo_.


5.2 MeSH Pharmacological Classification

Cyclooxygenase 2 Inhibitors

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


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
ETODOLAC
5.3.2 FDA UNII
2M36281008
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AB - Acetic acid derivatives and related substances

M01AB08 - Etodolac


5.5 Absorption, Distribution and Excretion

Absorption

Based on mass balance studies, the systemic bioavailability of etodolac from either the tablet or capsule formulation is at least 80%.


Route of Elimination

It is not known whether etodolac is excreted in human milk; however, based on its physical-chemical properties, excretion into breast milk is expected. Etodolac is extensively metabolized in the liver. The hydroxylated-etodolac metabolites undergo further glucuronidation followed by renal excretion and partial elimination in the feces (16% of dose). Approximately 1% of a etodolac dose is excreted unchanged in the urine with 72% of the dose excreted into urine as parent drug plus metabolite.


Volume of Distribution

390 mL/kg


Clearance

Oral cl=49.1 mL/h/kg [Normal healthy adults]

Oral cl=49.4 mL/h/kg [Healthy males (18-65 years)]

Oral cl=35.7 mL/h/kg [Healthy females (27-65 years)]

Oral cl=45.7 mL/h/kg [Eldery (>65 years)]

Oral cl=58.3 mL/h/kg [Renal impairement (46-73 years)]

Oral cl=42.0 mL/h/kg [Hepatic impairement (34-60 years)]


5.6 Metabolism/Metabolites

Etodolac is extensively metabolized in the liver. Renal elimination of etodolac and its metabolites is the primary route of excretion (72%). Metabolites found in urine (with percents of the administered dose) are: unchanged etodolac (1%), etodolac glucuronide (13%), hydroxylated metabolites (6-, 7-, and 8-OH; 5%), hydroxylated metabolite glucuronides (20%), and unidentified metabolites (33%). Fecal excretion accounts for 16% of its elimination.


Etodolac has known human metabolites that include (2S,3S,4S,5R)-6-[2-(1,8-Diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

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


5.7 Biological Half-Life

Terminal t1/2, 7.3 ± 4.0 hours. Distribution t1/2, 0.71 ± 0.50 hours


5.8 Mechanism of Action

Similar to other NSAIDs, the anti-inflammatory effects of etodolac result from inhibition of the enzyme cycooxygenase (COX). This decreases the synthesis of peripheral prostaglandins involved in mediating inflammation. Etodolac binds to the upper portion of the COX enzyme active site and prevents its substrate, arachidonic acid, from entering the active site. Etodolac was previously thought to be a non-selective COX inhibitor, but it is now known to be 5 50 times more selective for COX-2 than COX-1. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.


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08-Jan-2021
28-Aug-2024
KGS
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