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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

TargetsConditions

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

1077753600000
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

1077753600000
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

1077753600000
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

1077753600000
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

1214438400000
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

1077753600000
PubMed

PubMed

TitleDatePubMed
Role of human liver cytochrome P4503A in the metabolism of etoricoxib, a novel cyclooxygenase-2 selective inhibitor.
2001 Jun
Cox-2 inhibitors: today and tomorrow.
2002 Apr
Gateways to clinical trials.
2002 Dec
Simultaneous determination of unlabeled and carbon-13-labeled etoricoxib, a new cyclooxygenase-2 inhibitor, in human plasma using HPLC-MS/MS.
2002 Feb
Role of COX-2 inhibitors in the evolution of acute pain management.
2002 Jul
Gateways to Clinical Trials. June 2002.
2002 Jun
COX-2: where are we in 2003?--distinction from NSAIDs becoming blurred.
2003
Cox-2: where are we in 2003? - Cardiovascular risk and Cox-2 inhibitors.
2003
The gastrointestinal safety of the COX-2 selective inhibitor etoricoxib assessed by both endoscopy and analysis of upper gastrointestinal events.
2003 Aug
Clinical pharmacology of etoricoxib: a novel selective COX2 inhibitor.
2003 Feb
A literature review of the epidemiology and treatment of acute gout.
2003 Jun
Etoricoxib in the treatment of chronic pain.
2003 May
Pharmacokinetics of etoricoxib in patients with hepatic impairment.
2003 Oct
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
Clinical pharmacology of novel selective COX-2 inhibitors.
2004
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
Cyclooxygenase-2 inhibitors: do they have a role in emergency department prescribing?
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
Gastrointestinal side-effects of traditional non-steroidal anti-inflammatory drugs and new formulations.
2004 Jul
Etoricoxib in acute pain associated with dental surgery: a randomized, double-blind, placebo- and active comparator-controlled dose-ranging study.
2004 May
Gateways to clinical trials.
2004 Oct
Quantitation of itopride in human serum by high-performance liquid chromatography with fluorescence detection and its application to a bioequivalence study.
2005 Apr 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
Etoricoxib: a highly selective COX-2 inhibitor.
2005 May
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
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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