Etodolac

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

Etodolac
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa692015
Pregnancy
category
  • C
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Protein binding100%
Metabolismliver
Elimination half-life7.3 ± 4.0 hours
Excretionrenal
Identifiers
IUPAC name
  • (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 InfoCard100.157.848
Chemical and physical data
FormulaC17H21NO3
Molar mass287.359 g·mol−1
3D model (JSmol)
Melting point145 to 148 °C (293 to 298 °F)
Solubility in water3.92e-02 mg/mL [ALOGPS] mg/mL (20 °C)
SMILES
  • CCc2cccc3c1CCOC(CC)(CC(=O)O)c1[nH]c23
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) Y
  • Key:NNYBQONXHNTVIJ-UHFFFAOYSA-N Y
  (verify)

It was patented in 1971 and approved for medical use in 1985.[1] It was approved in the U.S. in 1991.[2]

Medical uses
See also: NSAIDs
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.

Post-marketing studies demonstrated that etodolac inhibition of cyclooxygenase is somewhat COX-2 selective [3] similar to celecoxib and other "COX-2 inhibitors." 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.[4]

In the UK, Etodolac is licensed for the treatment of inflammation and pain caused by osteoarthritis and rheumatoid arthritis.[5]

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. [6]

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. [2]

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.[7][8] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[7][8]

Brand names

Etodolac is manufactured by Almirall Limited under the trade name Lodine SR[9] and by Meda Pharmaceuticals under the name Eccoxolac.[10] Generic etodolac is also available.[11]

The drug is also sold under several other brand names, including:

  • "Etogesic" (India)
  • Etova (India)
  • Dualgan (Portugal)
  • Etodin (South Korea)
  • Etofree (India)
  • Etopan (Israel)
  • Flancox®[12] (Brazil)
  • Haipen (Japan)
  • Lodine (France, Switzerland, United States)
  • Proxym (S Etodolac) (India)
  • Etol (Turkey)
  • Lonine (Taiwan)
  • Etodine (Egypt)
  • Dolarit (Turkey)
  • "Etodin Fort" (Bulgaria)

References
  1. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 517. ISBN 9783527607495.
  2. Ogbru O. "etodolac, Lodine (Discontinued): Drug Facts, Side Effects and Dosing". MedicineNet.
  3. Warner TD, Giuliano F, Vojnovic I, Bukasa A, Mitchell JA, Vane JR (June 1999). "Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis". Proceedings of the National Academy of Sciences of the United States of America. 96 (13): 7563–8. Bibcode:1999PNAS...96.7563W. doi:10.1073/pnas.96.13.7563. PMC 22126. PMID 10377455.
  4. 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.
  5. BNF 55 - Etodolac
  6. 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.
  7. "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. This article incorporates text from this source, which is in the public domain.
  8. "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020. This article incorporates text from this source, which is in the public domain.
  9. "Lodine SR". medicines.org.uk. Archived from the original on 2008-03-18. Retrieved 2008-08-07.
  10. "Eccoxolac". medicines.org.uk. Archived from the original on 2012-12-24.
  11. "Etodolac preparations". BNF 55.
  12. "Flancox". apsen.com.br.
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