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{{Short description|Nonsteroidal anti-inflammatory drug}} |
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{{Cleanup|date=February 2008}} |
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{{refimprove|date=February 2008}} |
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{{Use dmy dates|date=November 2024}} |
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{{cs1 config |name-list-style=vanc |display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 415895204 |
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| verifiedrevid = 443747089 |
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| image = Etodolac.svg |
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| IUPAC_name = (''RS'')-2-(1,8-Diethyl-4,9-dihydro-3''H''-pyranoindol-1-yl)acetic acid |
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| width = |
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| image = Etodolac.svg |
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| alt = |
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| imagename = 1 : 1 mixture (racemate) |
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| width = 200px |
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| image2 = |
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| image2 = |
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| width2 = |
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| width2 = |
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| alt2 = |
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| imagename = <!-- else may use drug_name --> |
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<!--Clinical data--> |
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| drug_name = Etodolac |
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| tradename = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Drugs.com = {{drugs.com|monograph|etodolac}} |
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| MedlinePlus = a692015 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_category = |
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| routes_of_administration = ] |
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| ATC_prefix = M01 |
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| ATC_suffix = AB08 |
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| ATC_supplemental = |
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| legal_AU = S4 |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = POM |
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| legal_US = Rx-only |
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| legal_status = |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = 100% |
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| metabolism = liver |
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| elimination_half-life = 7.3 ± 4.0 hours |
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| excretion = renal |
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<!--Identifiers--> |
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| IUPHAR_ligand = 7185 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 41340-25-4 |
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| PubChem = 3308 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00749 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 3192 |
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| ChemSpiderID = 3192 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 2M36281008 |
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| UNII = 2M36281008 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChI = 1/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) |
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| KEGG = D00315 |
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| InChIKey = NNYBQONXHNTVIJ-UHFFFAOYAL |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 4909 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 622 |
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| ChEMBL = 622 |
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<!--Chemical data--> |
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| IUPAC_name = (''RS'')-2-(1,8-Diethyl-4,9-dihydro-3''H''-pyranoindol-1-yl)acetic acid |
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| C=17 | H=21 | N=1 | O=3 |
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| smiles = CCc2cccc3c1CCOC(CC)(CC(=O)O)c1c23 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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) |
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| StdInChI = 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NNYBQONXHNTVIJ-UHFFFAOYSA-N |
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| StdInChIKey = NNYBQONXHNTVIJ-UHFFFAOYSA-N |
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| synonyms = |
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| CAS_number = 41340-25-4 |
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| density = |
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| CAS_supplemental = |
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| melting_point = 145 |
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| ATC_prefix = M01 |
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| melting_high = 148 |
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| ATC_suffix = AB08 |
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| melting_notes = |
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| ATC_supplemental = |
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| ChEBI = 4909 |
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| boiling_point = |
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| solubility = 3.92e-02 mg/mL |
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| PubChem = 3308 |
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| specific_rotation = |
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| DrugBank = DB00749 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00315 |
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| chemical_formula = | C=17 | H=21 | N=1 | O=3 |
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| molecular_weight = 287.35 g/mol |
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| smiles = O=C(O)CC3(OCCc2c3nc1c(cccc12)CC)CC |
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| synonyms = |
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| density = |
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| melting_point = 145 |
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| melting_high = 148 |
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| melting_notes = |
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| boiling_point = |
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| boiling_notes = |
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| solubility = 3.92e-02 mg/mL |
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| specific_rotation = |
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| sec_combustion = |
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| bioavailability = |
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| protein_bound = 100% |
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| metabolism = liver |
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| elimination_half-life = 7.3 ± 4.0 hours |
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| excretion = renal |
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| licence_EU = <!-- EMEA requires brand name --> |
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| licence_US = <!-- FDA may use generic name --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category= C |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = POM |
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| legal_US = Rx-only |
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| legal_status = |
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| dependency_liability = |
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| routes_of_administration = oral |
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}} |
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}} |
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] |
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'''Etodolac''': Etodolac belongs to a class of drugs called nonsteroidal anti-inflammatory drugs (]s). Other members of this class include ], ] (Motrin, Advil, Nuprin, etc.), ] (Aleve, Naprosyn), ] (Indocin), ] (Relafen) and numerous others. These drugs are used for the management of mild to moderate pain, fever, and ]. They work by reducing the levels of ]s, which are chemicals that are responsible for pain and the fever and tenderness that occur with inflammation. Etodolac blocks the enzyme that makes ]s (cyclooxygenase), resulting in lower concentrations of prostaglandins. As a consequence, inflammation, pain and fever are reduced. The ] approved etodolac in January 1991.<ref name="medicinenet.com">http://www.medicinenet.com/etodolac/article.htm</ref> |
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<!-- Definition and medical uses --> |
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Post-marketing studies demonstrated that etodolac inhibition of ] is somewhat COX-2 selective <ref>http://www.pnas.org/content/96/13/7563.short</ref> similar to ] and other "]s." Unlike ], both etodolac and celecoxib can fully inhibit COX-1 and are designated as having "preferential selectivity" toward COX-2. Interestingly, the (inactive against COX) r-enantiomer of etodolac inhibits ] levels in ] cells.<ref>http://www.ncbi.nlm.nih.gov/pubmed/17275129</ref> |
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'''Etodolac''' is a ] (NSAID). |
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{{main|NSAIDs}} |
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<!-- Society and culture --> |
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==Preparations== |
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It was patented in 1971 and approved for medical use in 1985.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=517 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA517 |language=en}}</ref> It was approved in the U.S. in 1991.<ref name="medicinenet.com">{{cite web |url= http://www.medicinenet.com/etodolac/article.htm |title=etodolac, Lodine (Discontinued): Drug Facts, Side Effects and Dosing| vauthors = Ogbru O |work=MedicineNet }}</ref> |
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==Medical uses== |
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Etodolac is manufactured by Almirall Limited under the trade name '''Lodine SR'''<ref name="SPC1"></ref> and by Meda Pharmaceuticals under the name '''Eccoxolac'''.<ref name ="SPC2"></ref> Non-proprietary etodolac is also available <ref name="BNF Etodolac"></ref> |
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{{See also|NSAIDs}} |
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] |
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NSAIDs are used for the management of mild to moderate pain, fever, and ]. They work by reducing the levels of ]s, which are chemicals that are responsible for pain and the fever and tenderness that occur with inflammation. Etodolac blocks the ] (abbrev. COX) enzymes which form ]s, resulting in lower concentrations of ]s. As a consequence, inflammation, pain and fever are reduced. |
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Etodolac is 179 times more selective at blocking COX-2 than COX-1.<ref>{{Cite journal |last=Jones |first=Richard A. |date=1999-09-01 |title=Etodolac: An overview of a selective COX-2 inhibitor |url=https://link.springer.com/article/10.1007/s10787-999-0010-3 |journal=InflammoPharmacology |language=en |volume=7 |issue=3 |pages=269–275 |doi=10.1007/s10787-999-0010-3 |pmid=17638098 |issn=1568-5608}}</ref> Unlike ], both etodolac and celecoxib can fully inhibit ] and are designated as having "preferential selectivity" toward COX-2. The R-] of etodolac is inactive against COX enzymes, but inhibits ] levels in ] cells.<ref>{{cite journal | vauthors = Behari J, Zeng G, Otruba W, Thompson MD, Muller P, Micsenyi A, Sekhon SS, Leoni L, Monga SP | display-authors = 6 | title = R-Etodolac decreases beta-catenin levels along with survival and proliferation of hepatoma cells | journal = Journal of Hepatology | volume = 46 | issue = 5 | pages = 849–57 | date = May 2007 | pmid = 17275129 | pmc = 1924913 | doi = 10.1016/j.jhep.2006.11.017 }}</ref> |
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==Indications== |
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Etodolac is licensed for the ] of ] and pain caused by ] and ].<ref></ref> |
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In the UK, Etodolac is licensed for the ] of inflammation and pain caused by ] and ].<ref></ref> |
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==Dosing== |
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== Interactions == |
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Capsules: 200 and 300 mg; |
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Tablets: 400 and 500 mg; |
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Extended Release: 400, 500 and 600 mg. |
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The maximum recommended daily dosage of etodolac is 1000 mg. However, some patients have been found to benefit from daily dosage of 1200 mg. Daily dosages of Etodolac exceeding 1200 mg have not been evaluated. |
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<ref name="medicinenet.com"/> |
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Etodolac should be avoided by patients with a history of ] attacks, ], or other ] to ] or other NSAIDs. Rare but severe allergic reactions have been reported in such individuals. It also should be avoided by patients with ] disease or poor ], since this medication can worsen both conditions. Etodolac is used with caution in patients taking blood thinning medications (]s), such as ] (Coumadin), because it increases the risk of ]. Patients taking both ] and etodolac may develop toxic blood lithium levels. Additionally, etodolac has been found to interact with certain anti-depressant medications, such as ] or ], which can increase risks of stroke, heart attack, and other cardiovascular conditions. Patients also taking ] (Sandimmune) can develop kidney toxicity. Use in children has not been adequately studied. Etodolac is not habit-forming. NSAIDs should be discontinued prior to ] because of a mild interference with ] that is characteristic of this group of medicines. Etodolac is best discontinued at least four days in advance of surgery. Etodolac metabolites may also cause a false positive bilirubin result on a urinalysis test. <ref>{{cite journal | vauthors = Sho Y, Ishiodori T, Oketani M, Kubozono O, Nakamura A, Takeuchi A, Morino A, Arima T | display-authors = 6 | title = Effects of urinary metabolites of etodolac on diagnostic tests of bilirubin in urine | journal = Arzneimittel-Forschung | volume = 49 | issue = 7 | pages = 572–6 | date = July 1999 | pmid = 10442203 | doi = 10.1055/s-0031-1300464 | s2cid = 31642564 }}</ref> |
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==Interactions== |
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Etodolac should be avoided by patients with a history of ] attacks, ], or other ] to ] or other NSAIDs. Rare but severe allergic reactions have been reported in such individuals. It also should be avoided by patients with ] disease or poor ], since this medication can worsen both conditions. Etodolac is used with caution in patients taking blood thinning medications (]s), such as ] (Coumadin), because it increases the risk of ]. Patients taking both ] and Etodolac may develop toxic blood lithium levels. Additionally, Etodolac has been found to interact with certain anti-depressant medications, such as ] or ], can increase risks of stroke, heart attack, and other cardiovascular conditions. Patients also taking ] (Sandimmune) can develop kidney toxicity. Use in ] has not been adequately studied. Etodolac is not habit-forming. NSAIDs should be discontinued prior to elective surgery because of a mild interference with clotting that is characteristic of this group of medicines. Etodolac is best discontinued at least four days in advance of surgery. |
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Persons who have more than 3 alcoholic beverages per day are at increased risk of developing stomach ulcers when taking etodolac or other NSAIDs. |
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] |
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==Pregnancy and Nursing== |
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==Pregnancy and nursing== |
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Etodolac is generally avoided during ] and ]. ] may cause adverse cardiovascular effects in the fetus during pregnancy. |
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Etodolac is generally avoided during ] and ]. NSAIDs may cause adverse cardiovascular effects in the ] during pregnancy. |
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<ref name="medicinenet.com"/> |
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<ref name="medicinenet.com"/> |
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In October 2020, the U.S. ] (FDA) required the ] to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.<ref name="FDA PR 20201015" /><ref name="FDA safety 20201015" /> They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.<ref name="FDA PR 20201015">{{cite press release | title=FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications | website=U.S. ] (FDA) | date=15 October 2020 | url=https://www.fda.gov/news-events/press-announcements/fda-warns-using-type-pain-and-fever-medication-second-half-pregnancy-could-lead-complications | access-date=15 October 2020}} {{PD-notice}}</ref><ref name="FDA safety 20201015">{{cite web | title=NSAIDs may cause rare kidney problems in unborn babies | website=U.S. Food and Drug Administration | date=21 July 2017 | url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-recommends-avoiding-use-nsaids-pregnancy-20-weeks-or-later-because-they-can-result-low-amniotic | access-date=15 October 2020}} {{PD-notice}}</ref> |
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==Side Effects== |
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Etodolac may cause ], or ]s. It is advised to contact a physician if any of these ]s are severe or persistent: |
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], ], ] or ], ], ], ], ], ], ], ]. |
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Some side effects can be ''serious''. It is advised if any of the following symptoms occur to imediately contact a physician, and to discontinue use until such a time: |
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Unexplained ], ] of the ]s, ], ]s, ], ], ]s, ], ]s, or ]s, ] or ], ]s, ], ]ing, ], ], difficulty ]ing or ], yellowing of the skin or eyes, excessive ], unusual ] or ], lack of energy, ], pain in the upper right part of the ], ]-like symptoms, pale skin, fast ], cloudy, discolored, or ], difficult or painful ], ]. |
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== Brand names == |
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== Brand names == |
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Etodolac is manufactured by Almirall Limited under the brand name Lodine SR<ref name="SPC1">{{cite web|url=http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=3581|title=Lodine SR|work=medicines.org.uk|access-date=2008-08-07|archive-url=https://web.archive.org/web/20080318220946/http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=3581|archive-date=2008-03-18|url-status=dead}}</ref> and by Meda Pharmaceuticals under the name Eccoxolac.<ref name ="SPC2">{{cite web |url= http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=12573|archive-url= https://archive.today/20121224023132/http://emc.medicines.org.uk/emc/assets/c/html/displaydoc.asp?documentid=12573 |url-status=dead |archive-date=2012-12-24 |title=Eccoxolac |work=medicines.org.uk}}</ref> Generic etodolac is also available.<ref name="BNF Etodolac">{{cite web | url = http://www.bnf.org/bnf/bnf/current/127971.htm#this | work = BNF 55 | title = Etodolac preparations }}{{Dead link|date=March 2024 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> |
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The drug is sold under several brand names, including: |
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* '''Etopan''' (Turkey) |
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* '''Lodine''' (France) |
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Etodolac is also sold under several brand names, including: |
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==References== |
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* Etogesic (India) |
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* Etova (India) |
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* Dualgan / Sodolac (Portugal) |
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* Etodin (South Korea) |
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* Etofree (India) |
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* Etopan (Israel) |
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* Flancox<ref name="Flancox">{{cite web|url=http://www.apsen.com.br/bula.php?id_bula=5|title= Flancox |work=apsen.com.br|date= 2 April 2020 }}</ref> (Brazil) |
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* Haipen (Japan) |
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* Lodine (France, Switzerland, United States) |
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* Proxym (S Etodolac) (India) |
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* Dolarit, Edolar, Etol (Turkey) |
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* Lonine (Taiwan) |
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* Etodine (Egypt) |
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* Etodin Fort (Bulgaria) |
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== References == |
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{{reflist|2}} |
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{{reflist}} |
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==External links== |
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== External links == |
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{{Commons category}} |
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{{Commons category}} |
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* |
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* |
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{{Anti-inflammatory and antirheumatic products}} |
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{{Anti-inflammatory and antirheumatic products}} |
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{{NSAIDs}} |
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{{Analgesics}} |
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{{Analgesics}} |
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{{Prostanoidergics}} |
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{{Portal bar | Medicine}} |
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{{Authority control}} |
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