 | |
| Clinical data | |
|---|---|
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a692015 |
| Routes of administration | By mouth |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Protein binding | 100% |
| Metabolism | liver |
| Eliminationhalf-life | 7.3 ± 4.0 hours |
| Excretion | renal |
| Identifiers | |
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| CAS Number | |
| PubChemCID | |
| IUPHAR/BPS | |
| DrugBank |
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| ChemSpider |
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| UNII | |
| KEGG |
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| ChEBI | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.157.848 |
| 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) |
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Etodolac is anonsteroidal anti-inflammatory drug (NSAID).
It was patented in 1971 and approved for medical use in 1985.[2] It was approved in the U.S. in 1991.[3]
NSAIDs are used for the management of mild to moderate pain, fever, andinflammation. They work by reducing the levels ofprostaglandins, which are chemicals that are responsible for pain and the fever and tenderness that occur with inflammation. Etodolac blocks thecyclooxygenase (abbrev. COX) enzymes which formprostanoids, resulting in lower concentrations ofprostaglandins. As a consequence, inflammation, pain and fever are reduced.
Etodolac is 179 times more selective at blocking COX-2 than COX-1.[4] Unlikerofecoxib, both etodolac and celecoxib can fully inhibitCOX-1 and are designated as having "preferential selectivity" toward COX-2. The R-enantiomer of etodolac is inactive against COX enzymes, but inhibitsbeta-catenin levels inhepatoma cells.[5]
In the UK, Etodolac is licensed for thetreatment of inflammation and pain caused byosteoarthritis andrheumatoid arthritis.[6]
Etodolac should be avoided by patients with a history ofasthma attacks,hives, or otherallergic reactions toaspirin or other NSAIDs. Rare but severe allergic reactions have been reported in such individuals. It also should be avoided by patients withpeptic ulcer disease or poorkidney function, since this medication can worsen both conditions. Etodolac is used with caution in patients taking blood thinning medications (anticoagulants), such aswarfarin (Coumadin), because it increases the risk ofbleeding. Patients taking bothlithium and etodolac may develop toxic blood lithium levels. Additionally, etodolac has been found to interact with certain anti-depressant medications, such assertraline orfluoxetine, which can increase risks of stroke, heart attack, and other cardiovascular conditions. Patients also takingciclosporin (Sandimmune) can develop kidney toxicity. Use in children has not been adequately studied. Etodolac is not habit-forming. NSAIDs should be discontinued prior toelective surgery because of a mild interference withclotting 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.[1][7]
Etodolac is generally avoided duringpregnancy andnursing. NSAIDs may cause adverse cardiovascular effects in thefetus during pregnancy.[3]
In October 2020, the U.S.Food and Drug Administration (FDA) required thedrug 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]
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:
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This article incorporates text from this source, which is in thepublic domain. This article incorporates text from this source, which is in thepublic domain.
| pyrazolones / pyrazolidines | |
|---|---|
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;†withdrawn drugs;‡veterinary use. | |
