Etodolac

Last updated

Etodolac
Etodolac.svg
Clinical data
AHFS/Drugs.com Monograph
MedlinePlus a692015
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: WARNING [1] Rx-only
Pharmacokinetic data
Protein binding 100%
Metabolism liver
Elimination half-life 7.3 ± 4.0 hours
Excretion renal
Identifiers
  • (RS)-2-(1,8-Diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.157.848 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H21NO3
Molar mass 287.359 g·mol−1
3D model (JSmol)
Melting point 145 to 148 °C (293 to 298 °F)
Solubility in water 3.92e-02 mg/mL [ALOGPS] mg/mL (20 °C)
  • CCc2cccc3c1CCOC(CC)(CC(=O)O)c1[nH]c23
  • 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) Yes check.svgY
  • Key:NNYBQONXHNTVIJ-UHFFFAOYSA-N Yes check.svgY
   (verify)

Etodolac is a nonsteroidal anti-inflammatory drug (NSAID).

Contents

It was patented in 1971 and approved for medical use in 1985. [2] It was approved in the U.S. in 1991. [3]

Medical uses

Generic etodolac Etopen 200mg by Towa Pharmaceutical.jpg
Generic etodolac

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. [4] 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. [5]

In the UK, Etodolac is licensed for the treatment of inflammation and pain caused by osteoarthritis and rheumatoid arthritis. [6]

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. [7]

Box, strip and tablet of etodolac (Lodine SR) 600mg Etodolac600mg.jpg
Box, strip and tablet of etodolac (Lodine SR) 600mg

Pregnancy and nursing

Etodolac is generally avoided during pregnancy and nursing. NSAIDs may cause adverse cardiovascular effects in the fetus during pregnancy. [3]

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. [8] [9] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy. [8] [9]

Brand names

Etodolac is manufactured by Almirall Limited under the brand name Lodine SR [10] and by Meda Pharmaceuticals under the name Eccoxolac. [11] Generic etodolac is also available. [12]

Etodolac is also sold under several brand names, including:

Related Research Articles

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Ketoprofen is one of the propionic acid class of nonsteroidal anti-inflammatory drugs (NSAID) with analgesic and antipyretic effects. It acts by inhibiting the body's production of prostaglandin.

<span class="mw-page-title-main">Nonsteroidal anti-inflammatory drug</span> Class of therapeutic drug for relieving pain and inflammation

Non-steroidal anti-inflammatory drugs (NSAID) are members of a therapeutic drug class which reduces pain, decreases inflammation, decreases fever, and prevents blood clots. Side effects depend on the specific drug, its dose and duration of use, but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.

<span class="mw-page-title-main">Ibuprofen</span> Medication treating pain, fever, and inflammation

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<span class="mw-page-title-main">Diclofenac</span> Nonsteroidal anti-inflammatory drug

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<span class="mw-page-title-main">Naproxen</span> Nonsteroidal anti-inflammatory drug (NSAID) used to treat pain

Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, and inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and lasts for up to twelve hours. Naproxen is also available in salt form, naproxen sodium, which has better solubility when taken orally.

<span class="mw-page-title-main">Celecoxib</span> Nonsteroidal anti-inflammatory medication

Celecoxib, sold under the brand name Celebrex among others, is a COX-2 inhibitor and nonsteroidal anti-inflammatory drug (NSAID). It is used to treat the pain and inflammation in osteoarthritis, acute pain in adults, rheumatoid arthritis, psoriatic arthritis, ankylosing spondylitis, painful menstruation, and juvenile rheumatoid arthritis. It may also be used to decrease the risk of colorectal adenomas in people with familial adenomatous polyposis. It is taken by mouth. Benefits are typically seen within an hour.

Anti-inflammatory or antiphlogistic is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as opposed to opioids, which affect the central nervous system to block pain signaling to the brain.

Cyclooxygenase-2 inhibitors, also known as coxibs, are a type of nonsteroidal anti-inflammatory drug (NSAID) that directly target cyclooxygenase-2 (COX-2), an enzyme responsible for inflammation and pain. Targeting selectivity for COX-2 reduces the risk of peptic ulceration and is the main feature of celecoxib, rofecoxib, and other members of this drug class.

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<span class="mw-page-title-main">Piroxicam</span> Chemical compound

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<span class="mw-page-title-main">Ketorolac</span> Nonsteroidal anti-inflammatory drug (NSAID; analgesic)

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<span class="mw-page-title-main">Diflunisal</span> NSAID analgesic and anti-inflammatory drug

Diflunisal is a salicylic acid derivative with analgesic and anti-inflammatory activity. It was developed by Merck Sharp & Dohme in 1971, as MK647, after showing promise in a research project studying more potent chemical analogs of aspirin. It was first sold under the brand name Dolobid, marketed by Merck & Co., but generic versions are now widely available. It is classed as a nonsteroidal anti-inflammatory drug (NSAID) and is available in 250 mg and 500 mg tablets.

<span class="mw-page-title-main">Sulindac</span> Nonsteroidal anti-inflammatory drug (NSAID)

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<span class="mw-page-title-main">Nabumetone</span> NSAID analgesic and anti-inflammatory drug

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<span class="mw-page-title-main">Tolmetin</span> NSAID analgesic medication

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<span class="mw-page-title-main">Meclofenamic acid</span> Chemical compound

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<span class="mw-page-title-main">Fenoprofen</span> NSAID analgesic and anti-inflammatory drug

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References

  1. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 October 2023.
  2. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 517. ISBN   9783527607495.
  3. 1 2 Ogbru O. "etodolac, Lodine (Discontinued): Drug Facts, Side Effects and Dosing". MedicineNet.
  4. ↑ Jones RA (1 September 1999). "Etodolac: An overview of a selective COX-2 inhibitor". InflammoPharmacology. 7 (3): 269–275. doi:10.1007/s10787-999-0010-3. ISSN   1568-5608. PMID   17638098.
  5. ↑ Behari J, Zeng G, Otruba W, Thompson MD, Muller P, Micsenyi A, et al. (May 2007). "R-Etodolac decreases beta-catenin levels along with survival and proliferation of hepatoma cells". Journal of Hepatology. 46 (5): 849–57. doi:10.1016/j.jhep.2006.11.017. PMC   1924913 . PMID   17275129.{{cite journal}}: CS1 maint: overridden setting (link)
  6. ↑ BNF 55 - Etodolac
  7. ↑ Sho Y, Ishiodori T, Oketani M, Kubozono O, Nakamura A, Takeuchi A, et al. (July 1999). "Effects of urinary metabolites of etodolac on diagnostic tests of bilirubin in urine". Arzneimittel-Forschung. 49 (7): 572–6. doi:10.1055/s-0031-1300464. PMID   10442203. S2CID   31642564.{{cite journal}}: CS1 maint: overridden setting (link)
  8. 1 2 "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved 15 October 2020.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  9. 1 2 "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  10. ↑ "Lodine SR". medicines.org.uk. Archived from the original on 18 March 2008. Retrieved 7 August 2008.
  11. ↑ "Eccoxolac". medicines.org.uk. Archived from the original on 24 December 2012.
  12. ↑ "Etodolac preparations". BNF 55.[ permanent dead link ]
  13. ↑ "Flancox". apsen.com.br. 2 April 2020.
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