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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
Structure of ETODOLAC SODIUM

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

HIDE SMILES / InChI

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

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
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
The effect of NSAIDs and a COX-2 specific inhibitor on Helicobacter pylori-induced PGE2 and HGF in human gastric fibroblasts.
2000 Apr
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
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
Etodolac induces apoptosis and inhibits cell adhesion to bone marrow stromal cells in human myeloma cells.
2006 Feb
Membranous nephropathy associated with the relatively selective cyclooxygenase-2 inhibitor, etodolac, in a patient with early rheumatoid arthritis.
2007
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
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)
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:54:21 UTC 2023
Edited
by admin
on Sat Dec 16 01:54:21 UTC 2023
Record UNII
VIQ282YI0V
Record Status Validated (UNII)
Record Version
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Name Type Language
ETODOLAC SODIUM
Common Name English
PYRANO(3,4-B)INDOLE-1-ACETIC ACID, 1,8-DIETHYL-1,3,4,9-TETRAHYDRO-, MONOSODIUM SALT
Common Name English
SODIUM ETODOLATE
Common Name English
PYRANO(3,4-B)INDOLE-1-ACETIC ACID, 1,8-DIETHYL-1,3,4,9-TETRAHYDRO-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID50911859
Created by admin on Sat Dec 16 01:54:21 UTC 2023 , Edited by admin on Sat Dec 16 01:54:21 UTC 2023
PRIMARY
CAS
136067-30-6
Created by admin on Sat Dec 16 01:54:21 UTC 2023 , Edited by admin on Sat Dec 16 01:54:21 UTC 2023
SUPERSEDED
PUBCHEM
23665895
Created by admin on Sat Dec 16 01:54:21 UTC 2023 , Edited by admin on Sat Dec 16 01:54:21 UTC 2023
PRIMARY
CAS
110781-63-0
Created by admin on Sat Dec 16 01:54:21 UTC 2023 , Edited by admin on Sat Dec 16 01:54:21 UTC 2023
PRIMARY
FDA UNII
VIQ282YI0V
Created by admin on Sat Dec 16 01:54:21 UTC 2023 , Edited by admin on Sat Dec 16 01:54:21 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE