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Details

Stereochemistry ACHIRAL
Molecular Formula C18H15ClN2O2S.ClH
Molecular Weight 395.303
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETORICOXIB HYDROCHLORIDE

SMILES

Cl.CC1=NC=C(C=C1)C2=C(C=C(Cl)C=N2)C3=CC=C(C=C3)S(C)(=O)=O

InChI

InChIKey=NNGHGPAKTWAHHB-UHFFFAOYSA-N
InChI=1S/C18H15ClN2O2S.ClH/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23;/h3-11H,1-2H3;1H

HIDE SMILES / InChI
Etoricoxib is a selective COX-2 inhibitor, which is approved in Europe for the treatment of inflammatory disorders such as osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, acute pain conditions, gout and postoperative dental surgery pain.

CNS Activity

Curator's Comment: The drug crossed the blood brain barrier in rats.

Originator

Curator's Comment: # Merck Research Laboratories

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35354
Gene ID: 5743.0
Gene Symbol: PTGS2
Target Organism: Homo sapiens (Human)
5.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ARCOXIA

Approved Use

ARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis.

Launch Date

2004
Palliative
ARCOXIA

Approved Use

ARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis.

Launch Date

2004
Palliative
ARCOXIA

Approved Use

ARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis.

Launch Date

2004
Primary
ARCOXIA

Approved Use

ARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis.

Launch Date

2004
Palliative
ARCOXIA

Approved Use

ARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis.

Launch Date

2008
Primary
ARCOXIA

Approved Use

ARCOXIA is indicated in the symptomatic relief of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and the pain and signs of inflammation associated with acute gouty arthritis.

Launch Date

2004
PubMed

PubMed

TitleDatePubMed
A comparison of the therapeutic efficacy and tolerability of etoricoxib and diclofenac in patients with osteoarthritis.
2003
Treatment of chronic low back pain with etoricoxib, a new cyclo-oxygenase-2 selective inhibitor: improvement in pain and disability--a randomized, placebo-controlled, 3-month trial.
2003 Aug
The role of cyclooxygenase selective inhibitors in the gastrointestinal tract.
2003 Dec
[Rapidly acting and powerful antirheumatic drug now also approved in Germany. Arcoxia (etoricoxib, MSD)]].
2004
Etoricoxib reduced pain and disability and improved quality of life in patients with chronic low back pain: a 3 month, randomized, controlled trial.
2004
Economic evaluation of etoricoxib versus non-selective NSAIDs in the treatment of osteoarthritis and rheumatoid arthritis patients in the UK.
2004
A mechanistic perspective on the specificity and extent of COX-2 inhibition in pregnancy.
2004
Selective cyclooxygenase-2 inhibitors: similarities and differences.
2004
Clinical pharmacology of novel selective COX-2 inhibitors.
2004
[Pharmacology and classification of cyclooxygenase inhibitors].
2004 Apr
The second generation of COX-2 inhibitors: clinical pharmacological point of view.
2004 Aug
First and second generations of COX-2 selective inhibitors.
2004 Aug
Use of gastroprotective agents and discontinuations due to dyspepsia with the selective cyclooxygenase-2 inhibitor etoricoxib compared with non-selective NSAIDs.
2004 Dec
[Comparison of preemptive analgesia efficacy between etoricoxib and rofecoxib in ambulatory gynecological surgery].
2004 Dec
Isolation and structural characterization of the photolysis products of etoricoxib.
2004 Dec
Novel insights and therapeutical applications in the field of inhibitors of COX-2.
2004 Dec
Sulfone COX-2 inhibitors increase susceptibility of human LDL and plasma to oxidative modification: comparison to sulfonamide COX-2 inhibitors and NSAIDs.
2004 Dec
Cyclooxygenase-2 inhibitors: do they have a role in emergency department prescribing?
2004 Feb
Efficacy and safety profile of treatment with etoricoxib 120 mg once daily compared with indomethacin 50 mg three times daily in acute gout: a randomized controlled trial.
2004 Feb
Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials.
2004 Jan
Pharmacokinetics of etoricoxib in patients with renal impairment.
2004 Jan
Gateways to clinical trials.
2004 Jan-Feb
Gastrointestinal side-effects of traditional non-steroidal anti-inflammatory drugs and new formulations.
2004 Jul
Gateways to clinical trials.
2004 Jul-Aug
Etoricoxib.
2004 May
[Etoricoxib (Arcoxia)].
2004 May
Etoricoxib in acute pain associated with dental surgery: a randomized, double-blind, placebo- and active comparator-controlled dose-ranging study.
2004 May
Evaluation of quality of life following treatment with etoricoxib in patients with arthritis or low-back pain: an open label, uncontrolled pilot study in Mexico.
2004 May
Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic.
2004 May
A randomized, double-blind, parallel-group study comparing the analgesic effect of etoricoxib to placebo, naproxen sodium, and acetaminophen with codeine using the dental impaction pain model.
2004 May-Jun
Gateways to clinical trials.
2004 Nov
Gateways to clinical trials.
2004 Oct
The effects of modifying in vivo cytochrome P450 3A (CYP3A) activity on etoricoxib pharmacokinetics and of etoricoxib administration on CYP3A activity.
2004 Oct
Gateways to clinical trials.
2004 Sep
The analgesic efficacy of etoricoxib compared with oxycodone/acetaminophen in an acute postoperative pain model: a randomized, double-blind clinical trial.
2004 Sep
Cyclo-oxygenase-2 inhibitors: when should they be used in the elderly?
2005
Evaluation of the comparative efficacy of etoricoxib and ibuprofen for treatment of patients with osteoarthritis: A randomized, double-blind, placebo-controlled trial.
2005 Apr
Evaluation of the efficacy of etoricoxib in ankylosing spondylitis: results of a fifty-two-week, randomized, controlled study.
2005 Apr
Quantitation of itopride in human serum by high-performance liquid chromatography with fluorescence detection and its application to a bioequivalence study.
2005 Apr 25
The molecular basis for coxib inhibition of p38alpha MAP kinase.
2005 Aug 1
Validated liquid chromatographic ultraviolet method for the quantitation of Etoricoxib in human plasma using liquid-liquid extraction.
2005 Feb 25
Regulation of thrombomodulin expression in human vascular smooth muscle cells by COX-2-derived prostaglandins.
2005 Jan 7
Gateways to clinical trials.
2005 Jan-Feb
Valdecoxib: assessment of cyclooxygenase-2 potency and selectivity.
2005 Mar
A liquid chromatography-mass spectrometry method for the quantification of both etoricoxib and valdecoxib in human plasma.
2005 Mar
The incidence of upper gastrointestinal adverse events in clinical trials of etoricoxib vs. non-selective NSAIDs: an updated combined analysis.
2005 May
Etoricoxib: a highly selective COX-2 inhibitor.
2005 May
Efficacy of cyclo-oxygenase-2 inhibition by etoricoxib and naproxen on the axial manifestations of ankylosing spondylitis in the presence of peripheral arthritis.
2005 Nov
An overview of the recent developments in analytical methodologies for determination of COX-2 inhibitors in bulk drugs, pharmaceuticals and biological matrices.
2005 Sep 15
Simultaneous quantitation of etoricoxib, salicylic acid, valdecoxib, ketoprofen, nimesulide and celecoxib in plasma by high-performance liquid chromatography with UV detection.
2006 Jan
Patents

Sample Use Guides

The recommended dose is 30 mg once a day (osteoarthritis) and 60 mg once a day (rheumatoid arthritis, ankylosing spondylitis); the dose may be increased to a maximum of 60 mg (osteoarthritis) or 90 mg (rheumatoid arthritis, ankylosing spondylitis) once a day if needed. In case of acute pain conditions etoricoxib should be used only for the acute painful period. In gout the recommended dose is 120 mg once a day which should only be used for the acute painful period, limited to a maximum of 8 days. For the treatment of postoperative dental surgery pain the recommended dose is 90 mg once daily, limited to a maximum of 3 days treatment.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ETORICOXIB HYDROCHLORIDE
Common Name English
2,3'-BIPYRIDINE, 5-CHLORO-6'-METHYL-3-(4-(METHYLSULFONYL)PHENYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
L-791456 MONOHYDROCHLORIDE SALT
Common Name English
L-791456 HYDROCHLORIDE
Common Name English
2,3'-BIPYRIDINE, 5-CHLORO-6'-METHYL-3-(4-(METHYLSULFONYL)PHENYL)-, MONOHYDROCHLORIDE
Systematic Name English
Code System Code Type Description
PUBCHEM
17895326
Created by admin on Sat Dec 16 09:08:19 GMT 2023 , Edited by admin on Sat Dec 16 09:08:19 GMT 2023
PRIMARY
FDA UNII
138Y28RY5E
Created by admin on Sat Dec 16 09:08:19 GMT 2023 , Edited by admin on Sat Dec 16 09:08:19 GMT 2023
PRIMARY
CAS
202409-40-3
Created by admin on Sat Dec 16 09:08:19 GMT 2023 , Edited by admin on Sat Dec 16 09:08:19 GMT 2023
PRIMARY
DRUG BANK
DBSALT002328
Created by admin on Sat Dec 16 09:08:19 GMT 2023 , Edited by admin on Sat Dec 16 09:08:19 GMT 2023
PRIMARY