Etodolac
{{Short description|Nonsteroidal anti-inflammatory drug}}
{{Use dmy dates|date=November 2024}}
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{{Drugbox
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| image = Etodolac.svg
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| Drugs.com = {{drugs.com|monograph|etodolac}}
| MedlinePlus = a692015
| pregnancy_AU =
| pregnancy_category =
| routes_of_administration = By mouth
| ATC_prefix = M01
| ATC_suffix = AB08
| ATC_supplemental =
| legal_AU = S4
| legal_CA =
| legal_UK = POM
| legal_US = Rx-only
| legal_status =
| bioavailability =
| protein_bound = 100%
| metabolism = liver
| elimination_half-life = 7.3 ± 4.0 hours
| excretion = renal
| IUPHAR_ligand = 7185
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 41340-25-4
| PubChem = 3308
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00749
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3192
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2M36281008
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00315
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 4909
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 622
| IUPAC_name = (RS)-2-(1,8-Diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetic acid
| C=17 | H=21 | N=1 | O=3
| smiles = CCc2cccc3c1CCOC(CC)(CC(=O)O)c1[nH]c23
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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 = NNYBQONXHNTVIJ-UHFFFAOYSA-N
| synonyms =
| density =
| melting_point = 145
| melting_high = 148
| melting_notes =
| boiling_point =
| solubility = 3.92e-02 mg/mL [ALOGPS]
| specific_rotation =
}}
Etodolac is a nonsteroidal anti-inflammatory drug (NSAID).
It was patented in 1971 and approved for medical use in 1985.{{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}} It was approved in the U.S. in 1991.{{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 }}
Medical uses
{{See also|NSAIDs}}
File:Etopen 200mg by Towa Pharmaceutical.jpg
NSAIDs are used for the management of mild to moderate pain, fever, and inflammation. They work by reducing the levels of prostaglandins, which are chemicals that are responsible for pain and the fever and tenderness that occur with inflammation. Etodolac blocks the cyclooxygenase (abbrev. COX) enzymes which form prostanoids, resulting in lower concentrations of prostaglandins. As a consequence, inflammation, pain and fever are reduced.
Etodolac is 179 times more selective at blocking COX-2 than COX-1.{{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}} Unlike rofecoxib, both etodolac and celecoxib can fully inhibit COX-1 and are designated as having "preferential selectivity" toward COX-2. The R-enantiomer of etodolac is inactive against COX enzymes, but inhibits beta-catenin levels in hepatoma cells.{{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 }}
In the UK, Etodolac is licensed for the treatment of inflammation and pain caused by osteoarthritis and rheumatoid arthritis.[http://www.bnf.org/bnf/bnf/current/5216.htm BNF 55 - Etodolac]
Interactions
Etodolac should be avoided by patients with a history of asthma attacks, hives, or other allergic reactions to aspirin or other NSAIDs. Rare but severe allergic reactions have been reported in such individuals. It also should be avoided by patients with peptic ulcer disease or poor kidney function, since this medication can worsen both conditions. Etodolac is used with caution in patients taking blood thinning medications (anticoagulants), such as warfarin (Coumadin), because it increases the risk of bleeding. Patients taking both lithium and etodolac may develop toxic blood lithium levels. Additionally, etodolac has been found to interact with certain anti-depressant medications, such as sertraline or fluoxetine, which can increase risks of stroke, heart attack, and other cardiovascular conditions. Patients also taking ciclosporin (Sandimmune) can develop kidney toxicity. Use in children 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. Etodolac metabolites may also cause a false positive bilirubin result on a urinalysis test. [https://www.ncbi.nlm.nih.gov/pubmed/10442203]{{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 }}
Pregnancy and nursing
Etodolac is generally avoided during pregnancy and nursing. NSAIDs may cause adverse cardiovascular effects in the fetus during pregnancy.
In October 2020, the U.S. Food and Drug Administration (FDA) required the drug label 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. They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.{{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. Food and Drug Administration (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}}{{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}}
Brand names
Etodolac is manufactured by Almirall Limited under the brand name Lodine SR{{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}} and by Meda Pharmaceuticals under the name Eccoxolac.{{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}} Generic etodolac is also available.{{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 }}
Etodolac is also sold under several brand names, including:
- Etogesic (India)
- Etova (India)
- Dualgan / Sodolac (Portugal)
- Etodin (South Korea)
- Etofree (India)
- Etopan (Israel)
- Flancox{{cite web|url=http://www.apsen.com.br/bula.php?id_bula=5|title=Flancox|work=apsen.com.br|date=2 April 2020|access-date=22 September 2013|archive-date=16 September 2016|archive-url=https://web.archive.org/web/20160916195209/http://www.apsen.com.br/bula.php?id_bula=5|url-status=dead}} (Brazil)
- Haipen (Japan)
- Lodine (France, Switzerland, United States)
- Proxym (S Etodolac) (India)
- Dolarit, Edolar, Etol (Turkey)
- Lonene (Indonesia, Taiwan)
- Etodine (Egypt)
- Etodin Fort (Bulgaria)
References
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External links
{{Commons category}}
{{Anti-inflammatory and antirheumatic products}}
{{Analgesics}}
{{Prostanoidergics}}
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