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Etodolac

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a692015
Pregnancy category	C
Routes of administration	oral
ATC code	M01AB08 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: WARNINGRx-only
Pharmacokinetic data
Protein binding	100%
Metabolism	liver
Elimination half-life	7.3 ± 4.0 hours
Excretion	renal
Identifiers
IUPAC name (RS)-2-(1,8-Diethyl-4,9-dihydro-3H-pyranoindol-1-yl)acetic acid
CAS Number	41340-25-4
PubChem CID	3308
IUPHAR/BPS	7185
DrugBank	DB00749
ChemSpider	3192
UNII	2M36281008
KEGG	D00315
ChEBI	CHEBI:4909
ChEMBL	ChEMBL622
CompTox Dashboard (EPA)	DTXSID9020615
ECHA InfoCard	100.157.848
Chemical and physical data
Formula	C17H21NO3
Molar mass	287.35 g/mol g·mol
3D model (JSmol)	Interactive image
Melting point	145 to 148 °C (293 to 298 °F)
Solubility in water	3.92e-02 mg/mL  mg/mL (20 °C)
SMILES O=C(O)CC3(OCCc2c3nc1c(cccc12)CC)CC
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) Key:NNYBQONXHNTVIJ-UHFFFAOYSA-N
(verify)

Etodolac is a nonsteroidal anti-inflammatory drug (NSAID) approved by the U.S. Food and Drug Administration in January 1991.

As of 2015 the cost for a typical month of medication in the United States is less than 25 USD.

Medical uses

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 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.

Indications

Etodolac is licensed for the treatment of inflammation and pain caused by osteoarthritis and rheumatoid arthritis.

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.

Pregnancy and nursing

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

Brand names

Etodolac is manufactured by Almirall Limited under the trade name Lodine SR and by Meda Pharmaceuticals under the name Eccoxolac. Non-proprietary etodolac is also available

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

• Etova (India)
• Dualgan (Portugal)
• Etodin (South Korea)
• Etofree (India)
• Etopan (Israel)
• Flancox® (Brazil)
• Haipen (Japan)
• Lodine (France, Switzerland)
• Proxym (S Etodolac) (India)
• Etol (Turkey)
• Lonine (Taiwan)
• Etodine (Egypt)
• Dolarit (Turkey)

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 Oct 2023.
2. ^ Omudhome Ogbru, PharmD. "etodolac, Lodine (Discontinued): Drug Facts, Side Effects and Dosing". MedicineNet.
3. Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 7. ISBN 9781284057560.
4. Timothy D. Warner. "Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: A full in vitro analysis". pnas.org. {{cite web}}: line feed character in |title= at position 125 (help)
5. Behari, J; Zeng, G; Otruba, W; Thompson, MD; Muller, P; Micsenyi, A; Sekhon, SS; Leoni, L; Monga, SP (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.
6. BNF 55 - Etodolac
7. "Lodine SR". medicines.org.uk.
8. "Eccoxolac". medicines.org.uk.
9. BNF 55: Etodolac preparations
10. ":: Apsen ::". apsen.com.br.

External links

• DrugBank info
• Medicinenet.com

• Nonsteroidal anti-inflammatory drugs
• Acetic acids