U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H21NO3
Molecular Weight 287.3542
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETODOLAC

SMILES

CCc1cccc2c3CCOC(CC)(CC(=O)O)c3[nH]c12

InChI

InChIKey=NNYBQONXHNTVIJ-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
15.0 µM [IC50]
122.0 µM [IC50]
2.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Etodolac

Approved Use

Etodolac 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 Date

8.80416E11
Primary
Etodolac

Approved Use

Etodolac 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 Date

8.80416E11
Palliative
Etodolac

Approved Use

Etodolac 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 Date

8.80416E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
15.9 μg/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
65.8 μg × h/mL
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
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
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
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

Doses

DosePopulationAdverse 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%)
Diarrhea (2%)
Flatulence (1%)
Sources:
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

AEs

AESignificanceDosePopulation
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.
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
major
minor
minor
minor
minor
no
no
weak
weak
weak
weak
yes
yes
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Efficacy and tolerability of etodolac in aged patients affected by degenerative joint disease (osteoarthritis) in its active phase.
1994
Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor.
1997 May
Immune hemolytic anemia caused by sensitivity to a metabolite of etodolac, a nonsteroidal anti-inflammatory drug.
2000 Jun
Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs.
2004 Jun
The R-enantiomer of the nonsteroidal antiinflammatory drug etodolac binds retinoid X receptor and induces tumor-selective apoptosis.
2005 Feb 15
Etodolac, a selective cyclooxygenase-2 inhibitor, inhibits liver metastasis of colorectal cancer cells via the suppression of MMP-9 activity.
2006 Feb
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
Blurred vision and weakness in a 60-year-old woman.
2010 May
Sacroiliitis and severe disability due to isotretinoin therapy.
2010 May
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
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
Etodolac significantly reduced cell viability of FMS-1 cells in a dosedependent manner (0.125 mM - 1 mM)
Name Type Language
ETODOLAC
EP   GREEN BOOK   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
ETODOLAC [USP MONOGRAPH]
Common Name English
NAPILAC
Brand Name English
(+/-)-1,8-DIETHYL-1,3,4,9-TETRAHYDROPYRANO(3,4-B)INDOLE-1-ACETIC ACID
Systematic Name English
EDOLAN
Brand Name English
ETODOLAC [USAN]
Common Name English
ETODOLAC [USP-RS]
Common Name English
ZEDOLAC
Brand Name English
AY-24,236
Code English
TEDOLAN
Brand Name English
LODIN XL
Brand Name English
AY-24236
Code English
ETODOLIC ACID
Common Name English
ETODOLAC [MI]
Common Name English
PYRANO(3,4-B)INDOLE-1-ACETIC ACID, 1,8-DIETHYL-1,3,4,9-TETRAHYDRO-(+/-)-
Common Name English
1,8-DIETHYL-1,3,4,9-TETRAHYDROPYRANO(3,4-B)INDOL-1-ACETIC ACID
Systematic Name English
ETODOLAC [INN]
Common Name English
(+/-)-ETODOLAC
Common Name English
ETODOLAC [VANDF]
Common Name English
FLANCOX
Brand Name English
PYRANO(3,4-B)INDOLE-1-ACETIC ACID, 1,8-DIETHYL-1,3,4,9-TETRAHYDRO-
Systematic Name English
1,8-DIETHYL-1,3,4,9-TETRAHYDROPYRANO(3,4-B)INDOLE-1-ACETIC ACID
Systematic Name English
RAMODAR
Brand Name English
LODINE
Brand Name English
ETODOLAC [MART.]
Common Name English
(RS)-ETODOLIC ACID
Common Name English
NIH-9918
Code English
NSC-282126
Code English
ETODOLAC [EP MONOGRAPH]
Common Name English
ULTRADOL
Brand Name English
ETODOLAC [GREEN BOOK]
Common Name English
ECCOXOLAC
Brand Name English
AY-24-236
Code English
ETODOLAC [WHO-DD]
Common Name English
ETODOLAC [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
FDA ORPHAN DRUG 454614
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
WHO-VATC QM01AB08
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
FDA ORPHAN DRUG 475715
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
NDF-RT N0000175722
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
CFR 21 CFR 520.870
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
LIVERTOX 387
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
CFR 21 CFR 522.870
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
FDA ORPHAN DRUG 484315
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
WHO-ATC M01AB08
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
NDF-RT N0000000160
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
NDF-RT N0000175721
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
Code System Code Type Description
PUBCHEM
3308
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
WIKIPEDIA
ETODOLAC
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
RXCUI
24605
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00749
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
NCI_THESAURUS
C47526
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
LACTMED
Etodolac
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
EVMPD
SUB07316MIG
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
IUPHAR
7185
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
DRUG CENTRAL
1103
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
INN
3715
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
CAS
41340-25-4
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
MESH
D017308
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
FDA UNII
2M36281008
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
ChEMBL
CHEMBL622
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY
MERCK INDEX
M5190
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1268706
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY USP-RS
CAS
87226-38-8
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
SUPERSEDED
EPA CompTox
41340-25-4
Created by admin on Fri Jun 25 20:56:09 UTC 2021 , Edited by admin on Fri Jun 25 20:56:09 UTC 2021
PRIMARY