Details
Stereochemistry | RACEMIC |
Molecular Formula | C17H20NO3.Na |
Molecular Weight | 309.3354 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCC1=CC=CC2=C1NC3=C2CCOC3(CC)CC([O-])=O
InChI
InChIKey=OYVVSFKYBAVZJZ-UHFFFAOYSA-M
InChI=1S/C17H21NO3.Na/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);/q;+1/p-1
Molecular Formula | C17H20NO3 |
Molecular Weight | 286.3456 |
Charge | -1 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00749Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/etodolac.html
Sources: http://www.drugbank.ca/drugs/DB00749
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/etodolac.html
Etodolac is an anti-inflammatory agent with analgesic and antipyretic properties. It is used to treat osteoarthritis, rheumatoid arthritis and control acute pain. The therapeutic effects of etodolac are achieved via inhibition of the synthesis of prostaglandins involved in fever, pain, swelling and inflammation. Etodolac is administered as a racemate. As with other NSAIDs, the S-form has been shown to be active while the R-form is inactive. Both enantiomers are stable and there is no evidence of R- to S- conversion in vivo. Similar to other NSAIDs, the anti-inflammatory effects of etodolac result from inhibition of the enzyme cycooxygenase (COX). This decreases the synthesis of peripheral prostaglandins involved in mediating inflammation. Etodolac binds to the upper portion of the COX enzyme active site and prevents its substrate, arachidonic acid, from entering the active site. Etodolac was previously thought to be a non-selective COX inhibitor, but it is now known to be 5 – 50 times more selective for COX-2 than COX-1. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss. Etodolac is used for acute and long-term management of signs and symptoms of osteoarthritis and rheumatoid arthritis, as well as for the management of pain. Lodine, the brand-name formulation of the drug, has been discontinued in the United States, and only the generic form of etodolac is available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12511226 |
15.0 µM [IC50] | ||
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9650852 |
122.0 µM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18752957 |
2.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Etodolac Approved UseEtodolac Capsules and Tablets, USP are indicated:
For acute and long-term use in the management of signs and symptoms of the following:
Osteoarthritis
Rheumatoid arthritis
For the management of acute pain Launch Date1997 |
|||
Primary | Etodolac Approved UseEtodolac Capsules and Tablets, USP are indicated:
For acute and long-term use in the management of signs and symptoms of the following:
Osteoarthritis
Rheumatoid arthritis
For the management of acute pain Launch Date1997 |
|||
Sources: https://www.drugs.com/pro/etodolac.html |
Palliative | Etodolac Approved UseEtodolac Capsules and Tablets, USP are indicated:
For acute and long-term use in the management of signs and symptoms of the following:
Osteoarthritis
Rheumatoid arthritis
For the management of acute pain Launch Date1997 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2525981/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
17.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2525981/ |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
14.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2938343/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
65.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2525981/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
81 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2525981/ |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
84 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2938343/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2525981/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
6.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2525981/ |
200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
6.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2938343/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
ETODOLAC serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 55.2 (31-64) n = 493 Health Status: unhealthy Condition: osteoarthritis Age Group: 55.2 (31-64) Sex: M+F Population Size: 493 Sources: |
Disc. AE: Abdominal pain, Diarrhea... AEs leading to discontinuation/dose reduction: Abdominal pain (2%) Sources: Diarrhea (2%) Flatulence (1%) |
1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: Page: 0654D-357-US, -358-US, -370-US, and -371-US. |
unhealthy, 55.2 (31-64) n = 493 Health Status: unhealthy Condition: osteoarthritis Age Group: 55.2 (31-64) Sex: M+F Population Size: 493 Sources: Page: 0654D-357-US, -358-US, -370-US, and -371-US. |
Disc. AE: Insomnia... AEs leading to discontinuation/dose reduction: Insomnia (<1%) Sources: Page: 0654D-357-US, -358-US, -370-US, and -371-US. |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Flatulence | 1% Disc. AE |
1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 55.2 (31-64) n = 493 Health Status: unhealthy Condition: osteoarthritis Age Group: 55.2 (31-64) Sex: M+F Population Size: 493 Sources: |
Abdominal pain | 2% Disc. AE |
1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 55.2 (31-64) n = 493 Health Status: unhealthy Condition: osteoarthritis Age Group: 55.2 (31-64) Sex: M+F Population Size: 493 Sources: |
Diarrhea | 2% Disc. AE |
1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: |
unhealthy, 55.2 (31-64) n = 493 Health Status: unhealthy Condition: osteoarthritis Age Group: 55.2 (31-64) Sex: M+F Population Size: 493 Sources: |
Insomnia | <1% Disc. AE |
1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: Page: 0654D-357-US, -358-US, -370-US, and -371-US. |
unhealthy, 55.2 (31-64) n = 493 Health Status: unhealthy Condition: osteoarthritis Age Group: 55.2 (31-64) Sex: M+F Population Size: 493 Sources: Page: 0654D-357-US, -358-US, -370-US, and -371-US. |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak [IC50 122 uM] | ||||
weak [IC50 50 uM] | ||||
yes [Ki 64 uM] | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
major | ||||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
weak | ||||
weak | ||||
weak | ||||
weak | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[Allergic vasculitis caused by etodolac. The first case]. | 1989 |
|
Efficacy and tolerability of etodolac in aged patients affected by degenerative joint disease (osteoarthritis) in its active phase. | 1994 |
|
Anti-inflammatory effects of etodolac: comparison with other non-steroidal anti-inflammatory drugs. | 1994 Dec |
|
Fulminant hepatic failure associated with etodolac use. | 1995 Apr |
|
Nonsteroidal antiinflammatory drug induced hypersensitivity vasculitis clinically mimicking temporal arteritis. | 1996 Jan |
|
Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. | 1997 May |
|
Reactive oxygen species are involved in the apoptosis induced by nonsteroidal anti-inflammatory drugs in cultured gastric cells. | 1999 Nov 3 |
|
The effect of NSAIDs and a COX-2 specific inhibitor on Helicobacter pylori-induced PGE2 and HGF in human gastric fibroblasts. | 2000 Apr |
|
Sulindac and a cyclooxygenase-2 inhibitor, etodolac, increase APC mRNA in the colon of rats treated with azoxymethane. | 2000 Dec |
|
Immune hemolytic anemia caused by sensitivity to a metabolite of etodolac, a nonsteroidal anti-inflammatory drug. | 2000 Jun |
|
Cyclooxygenase-1 and cyclooxygenase-2 selectivity of non-steroidal anti-inflammatory drugs: investigation using human peripheral monocytes. | 2001 Dec |
|
Selective cyclooxygenase-2 inhibitors show a differential ability to inhibit proliferation and induce apoptosis of colon adenocarcinoma cells. | 2002 Nov 6 |
|
Search of antimicrobial activity of selected non-antibiotic drugs. | 2002 Nov-Dec |
|
Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. | 2004 Jun |
|
Carboxyl nonsteroidal anti-inflammatory drugs are efficiently glucuronidated by microsomes of the human gastrointestinal tract. | 2004 Nov 18 |
|
The R-enantiomer of the nonsteroidal antiinflammatory drug etodolac binds retinoid X receptor and induces tumor-selective apoptosis. | 2005 Feb 15 |
|
Etodolac inhibits EBER expression and induces Bcl-2-regulated apoptosis in Burkitt's lymphoma cells. | 2005 Sep |
|
Combination of cyclooxygenase-2 inhibitors and oxaliplatin increases the growth inhibition and death in human colon cancer cells. | 2005 Sep 1 |
|
Ocular adverse effects associated with cyclooxygenase-2 inhibitors. | 2006 Feb |
|
Etodolac, a selective cyclooxygenase-2 inhibitor, inhibits liver metastasis of colorectal cancer cells via the suppression of MMP-9 activity. | 2006 Feb |
|
Etodolac induces apoptosis and inhibits cell adhesion to bone marrow stromal cells in human myeloma cells. | 2006 Feb |
|
Involvement of cyclooxygenase-2 in allergic nasal inflammation in rats. | 2006 Nov |
|
Membranous nephropathy associated with the relatively selective cyclooxygenase-2 inhibitor, etodolac, in a patient with early rheumatoid arthritis. | 2007 |
|
One center's experience: the serology and drugs associated with drug-induced immune hemolytic anemia--a new paradigm. | 2007 Apr |
|
Safety of selective cyclooxygenase-2 inhibitors and a basic non-steroidal anti-inflammatory drug (NSAID) in Japanese patients with NSAID-induced urticaria and/or angioedema: Comparison of meloxicam, etodolac and tiaramide. | 2007 Mar |
|
Spectrophotometric determination of etodolac in pure form and pharmaceutical formulations. | 2008 Apr 14 |
|
In vitro inhibition of CYP1A2 by model inhibitors, anti-inflammatory analgesics and female sex steroids: predictability of in vivo interactions. | 2008 Aug |
|
Dextran-etodolac conjugates: synthesis, in vitro and in vivo evaluation. | 2009 Mar-Apr |
|
Blurred vision and weakness in a 60-year-old woman. | 2010 May |
|
Sacroiliitis and severe disability due to isotretinoin therapy. | 2010 May |
|
Assessing the cardiovascular risk between celecoxib and nonselective nonsteroidal antiinflammatory drugs in patients with rheumatoid arthritis and osteoarthritis. | 2014 |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/etodolac.html
Usual Adult Dose for Osteoarthritis or Rheumatoid Arthritis
Capsules or tablets: 300 mg orally 2 to 3 times a day or 400 mg orally twice a day or 500 mg orally twice a day. Total daily dose should not exceed 1200 mg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24516579
Etodolac significantly reduced cell viability of FMS-1 cells in a dosedependent
manner (0.125 mM - 1 mM)
Substance Class |
Chemical
Created
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Record UNII |
VIQ282YI0V
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Record Status |
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Record Version |
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |