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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

Description

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Etodolac
Primary
Etodolac
Palliative
Etodolac

Cmax

ValueDoseCo-administeredAnalytePopulation
15.9 μg/mL
200 mg single, oral
ETODOLAC serum
Homo sapiens
17.8 μg/mL
200 mg 2 times / day multiple, oral
ETODOLAC serum
Homo sapiens
14.5 μg/mL
200 mg single, oral
ETODOLAC serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
65.8 μg × h/mL
200 mg single, oral
ETODOLAC serum
Homo sapiens
81 μg × h/mL
200 mg 2 times / day multiple, oral
ETODOLAC serum
Homo sapiens
84 μg × h/mL
200 mg single, oral
ETODOLAC serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
200 mg single, oral
ETODOLAC serum
Homo sapiens
6.5 h
200 mg 2 times / day multiple, oral
ETODOLAC serum
Homo sapiens
6.1 h
200 mg single, oral
ETODOLAC serum
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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
In Vitro Use Guide
Etodolac significantly reduced cell viability of FMS-1 cells in a dosedependent manner (0.125 mM - 1 mM)