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Details

Stereochemistry ACHIRAL
Molecular Formula C18H15ClN2O2S
Molecular Weight 358.8436
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETORICOXIB

SMILES

Cc1ccc(cn1)-c2c(cc(cn2)Cl)-c3ccc(cc3)S(=O)(=O)C

InChI

InChIKey=MNJVRJDLRVPLFE-UHFFFAOYSA-N
InChI=1S/C18H15ClN2O2S/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

HIDE SMILES / InChI

Molecular Formula C18H15ClN2O2S
Molecular Weight 358.8436
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1.07775361E12
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

1.07775361E12
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

1.07775361E12
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

1.07775361E12
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

1.21443844E12
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

1.07775361E12
PubMed

PubMed

TitleDatePubMed
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
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
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
Pharmacological characterisation of a rat model of incisional pain.
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 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 Sep
The analgesic efficacy of etoricoxib compared with oxycodone/acetaminophen in an acute postoperative pain model: a randomized, double-blind clinical trial.
2004 Sep
Economic evaluation of etoricoxib versus non-selective NSAIDs in the treatment of osteoarthritis and rheumatoid arthritis patients in the UK.
2005
Cyclo-oxygenase-2 inhibitors: when should they be used in the elderly?
2005
Gateways to clinical trials.
2005 Apr
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
[COX-2 inhibitors--one step forward and two steps back].
2005 Apr 7
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
The analgesic effect of etoricoxib relative to that of cetaminophen analgesics: a randomized, controlled single-dose study in acute dental impaction pain.
2005 Jan
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
Relative thromboembolic risks associated with COX-2 inhibitors.
2005 Jul-Aug
Protective effects of etoricoxib, a selective inhibitor of cyclooxygenase-2, in experimental periodontitis in rats.
2005 Jun
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
Association between health-related quality of life and clinical efficacy endpoints in rheumatoid arthritis patients after four weeks treatment with anti-inflammatory agents.
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:02:26 UTC 2021
Edited
by admin
on Sat Jun 26 08:02:26 UTC 2021
Record UNII
WRX4NFY03R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETORICOXIB
INN   MART.   MI   USAN   USP-RS   WHO-DD  
USAN   INN  
Official Name English
MK-0663
Code English
ETORICOXIB [MI]
Common Name English
5-CHLORO-6'-METHYL-3-(4-(METHYLSULFONYL)PHENYL)-2,3'-BIPYRIDINE
Systematic Name English
ARCOXIA
Brand Name English
ETORICOXIB [USAN]
Common Name English
L-791456
Code English
ETORICOXIB [MART.]
Common Name English
ETORICOXIB [WHO-DD]
Common Name English
2,3'-BIPYRIDINE, 5-CHLORO-6'-METHYL-3-(4-(METHYLSULFONYL)PHENYL)-
Systematic Name English
ETORICOXIB [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC M01AH05
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
WHO-VATC QM01AH05
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
NCI_THESAURUS C1323
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
Code System Code Type Description
IUPHAR
2896
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
DRUG CENTRAL
1113
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
ChEMBL
CHEMBL416146
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
PUBCHEM
123619
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
MERCK INDEX
M5200
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY Merck Index
EVMPD
SUB16429MIG
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
CAS
202409-33-4
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
INN
8082
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
NCI_THESAURUS
C52188
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
WIKIPEDIA
ETORICOXIB
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
RXCUI
307296
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY RxNorm
FDA UNII
WRX4NFY03R
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
EPA CompTox
202409-33-4
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
DRUG BANK
DB01628
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
MESH
C422649
Created by admin on Sat Jun 26 08:02:27 UTC 2021 , Edited by admin on Sat Jun 26 08:02:27 UTC 2021
PRIMARY
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Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

ORAL SOLUTION DOSE

Tmax PHARMACOKINETIC ORAL SOLUTION DOSE

ORAL ADMINISTRATION

ORAL BIOAVAILABILITY PHARMACOKINETIC