Etodolac

Etodolac

Systematic (IUPAC) name
(RS)-2-(1,8-Diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetic acid
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a692015
Pregnancy cat.	C
Legal status	POM (UK) ℞-only (US)
Routes	oral
Pharmacokinetic data
Protein binding	100%
Metabolism	liver
Half-life	7.3 ± 4.0 hours
Excretion	renal
Identifiers
CAS number	41340-25-4
ATC code	M01AB08
PubChem	CID 3308
DrugBank	DB00749
ChemSpider	3192 Y
UNII	2M36281008 Y
KEGG	D00315 Y
ChEBI	CHEBI:4909 Y
ChEMBL	CHEMBL622 Y
Chemical data
Formula	C17H21NO3
Mol. mass	287.35 g/mol
SMILES	eMolecules & PubChem
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
Physical data
Melt. point	145–148 °C (293–298 °F)
Solubility in water	3.92e-02 mg/mL [ALOGPS] mg/mL (20 °C)
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Generic brand of Etodolac

Etodolac: Etodolac belongs to a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). Other members of this class include aspirin, ibuprofen (Motrin, Advil, Nuprin, etc.), naproxen (Aleve, Naprosyn), indomethacin (Indocin), nabumetone (Relafen) and numerous others. These drugs 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 enzyme that makes prostaglandins (cyclooxygenase), resulting in lower concentrations of prostaglandins. As a consequence, inflammation, pain and fever are reduced. The U.S. Food and Drug Administration approved etodolac in January 1991.

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. Interestingly, the (inactive against COX) r-enantiomer of etodolac inhibits beta-catenin levels in hepatoma cells.

Main article: NSAIDs

Preparations

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

Indications

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

Dosing

Capsules: 200 and 300 mg; Tablets: 400 and 500 mg; Extended Release: 400, 500 and 600 mg. 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.

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.

Persons who have more than 3 alcoholic beverages per day are at increased risk of developing stomach ulcers when taking etodolac or other NSAIDs.

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.

Side effects

Etodolac may cause side effects, or adverse drug reactions. It is advised to contact a physician if any of these symptoms are severe or persistent:

Constipation, diarrhea, gas or bloating, vomiting, headache, dizziness, ringing in the ears, runny nose, sore throat, blurred vision.

Some side effects can be serious. It is advised if any of the following symptoms occur to immediately contact a physician, and to discontinue use until such a time:

Unexplained weight gain, swelling of the eyes, face, lips, tongue, throat, hands, feet, ankles, or lower legs, fever or chills, blisters, rash, itching, hives, hoarseness, difficulty breathing or swallowing, yellowing of the skin or eyes, excessive tiredness, unusual bleeding or bruising, lack of energy, loss of appetite, pain in the upper right part of the stomach, flu-like symptoms, pale skin, fast heartbeat, cloudy, discolored, or bloody urine, difficult or painful urination, back pain.

Brand names

The drug is sold under several brand names, including:

• Etopan (Turkey)
• Lodine (France)
• Etofree (India)

External links

• DrugBank info
• Medicinenet.com