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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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    05-Jan-2021
    13-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    Fillers, Diluents & Binders

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    Coating Systems & Additives

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    Direct Compression

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    Controlled & Modified Release

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    Thickeners and Stabilizers

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    Solubilizers

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    Disintegrants & Superdisintegrants

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    Granulation

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    Topical

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    Lubricants & Glidants

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    Film Formers & Plasticizers

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    Co-Processed Excipients

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    Parenteral

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    Empty Capsules

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    Emulsifying Agents

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    API Stability Enhancers

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    Taste Masking

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    Rheology Modifiers

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    Surfactant & Foaming Agents

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    Coloring Agents

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    Vegetarian Capsules

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    Chewable & Orodispersible Aids

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    REF. STANDARDS & IMPURITIES

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