ETORICOXIB

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H15ClN2O2S
Molecular Weight	358.842
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

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	358.842
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin G/H synthase 2 47 Target ID: P35354 Gene ID: 5743.0 Gene Symbol: PTGS2 Target Organism: Homo sapiens (Human) Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Inhibitor 8228		5.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Palliative	Approved 8360	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
Rheumatoid arthritis 313 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Palliative	Approved 8360	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
Acute gouty arthritis 2 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Palliative	Approved 8360	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
Pain 608 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Primary	Approved 8360	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
Ankylosing spondylitis 33 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Palliative	Approved 8360	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
Postoperative dental surgery pain 2 Sources: https://www.medicines.org.uk/emc/PIL.29146.latest.pdf	Primary	Approved 8360	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

Title	Date	PubMed
[Rapidly acting and powerful antirheumatic drug now also approved in Germany. Arcoxia (etoricoxib, MSD)]].	2004	15675401
Etoricoxib reduced pain and disability and improved quality of life in patients with chronic low back pain: a 3 month, randomized, controlled trial.	2004	15370723
Economic evaluation of etoricoxib versus non-selective NSAIDs in the treatment of osteoarthritis and rheumatoid arthritis patients in the UK.	2004	15244490
A mechanistic perspective on the specificity and extent of COX-2 inhibition in pregnancy.	2004	15141994
Selective cyclooxygenase-2 inhibitors: similarities and differences.	2004	15124935
[Pharmacology and classification of cyclooxygenase inhibitors].	2004 Apr	15366670
The second generation of COX-2 inhibitors: clinical pharmacological point of view.	2004 Aug	15279595
First and second generations of COX-2 selective inhibitors.	2004 Aug	15279593
Use of gastroprotective agents and discontinuations due to dyspepsia with the selective cyclooxygenase-2 inhibitor etoricoxib compared with non-selective NSAIDs.	2004 Dec	15701208
[Comparison of preemptive analgesia efficacy between etoricoxib and rofecoxib in ambulatory gynecological surgery].	2004 Dec	15663229
Isolation and structural characterization of the photolysis products of etoricoxib.	2004 Dec	15638077
Novel insights and therapeutical applications in the field of inhibitors of COX-2.	2004 Dec	15579005
Sulfone COX-2 inhibitors increase susceptibility of human LDL and plasma to oxidative modification: comparison to sulfonamide COX-2 inhibitors and NSAIDs.	2004 Dec	15530895
Cyclooxygenase-2 inhibitors: do they have a role in emergency department prescribing?	2004 Feb	15239758
Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials.	2004 Jan	14996519
Gastrointestinal side-effects of traditional non-steroidal anti-inflammatory drugs and new formulations.	2004 Jul	15335413
Gateways to clinical trials.	2004 Jul-Aug	15349141
Etoricoxib.	2004 May	15319795
[Etoricoxib (Arcoxia)].	2004 May	15270001
Etoricoxib in acute pain associated with dental surgery: a randomized, double-blind, placebo- and active comparator-controlled dose-ranging study.	2004 May	15220011
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	15140335
Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic.	2004 May	15117884
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	15100590
Gateways to clinical trials.	2004 Nov	15632957
Gateways to clinical trials.	2004 Oct	15605126
The effects of modifying in vivo cytochrome P450 3A (CYP3A) activity on etoricoxib pharmacokinetics and of etoricoxib administration on CYP3A activity.	2004 Oct	15342613
Gateways to clinical trials.	2004 Sep	15538546
The analgesic efficacy of etoricoxib compared with oxycodone/acetaminophen in an acute postoperative pain model: a randomized, double-blind clinical trial.	2004 Sep	15333415
Economic evaluation of etoricoxib versus non-selective NSAIDs in the treatment of osteoarthritis and rheumatoid arthritis patients in the UK.	2005	15987231
Cyclo-oxygenase-2 inhibitors: when should they be used in the elderly?	2005	15813652
Gateways to clinical trials.	2005 Apr	15834452
Evaluation of the comparative efficacy of etoricoxib and ibuprofen for treatment of patients with osteoarthritis: A randomized, double-blind, placebo-controlled trial.	2005 Apr	15819283
Evaluation of the efficacy of etoricoxib in ankylosing spondylitis: results of a fifty-two-week, randomized, controlled study.	2005 Apr	15818702
Quantitation of itopride in human serum by high-performance liquid chromatography with fluorescence detection and its application to a bioequivalence study.	2005 Apr 25	15734161
[COX-2 inhibitors--one step forward and two steps back].	2005 Apr 7	15815733
The molecular basis for coxib inhibition of p38alpha MAP kinase.	2005 Aug 1	15990304
Validated liquid chromatographic ultraviolet method for the quantitation of Etoricoxib in human plasma using liquid-liquid extraction.	2005 Feb 25	15664353
The analgesic effect of etoricoxib relative to that of cetaminophen analgesics: a randomized, controlled single-dose study in acute dental impaction pain.	2005 Jan	15881486
Regulation of thrombomodulin expression in human vascular smooth muscle cells by COX-2-derived prostaglandins.	2005 Jan 7	15591227
Gateways to clinical trials.	2005 Jan-Feb	15834459
Relative thromboembolic risks associated with COX-2 inhibitors.	2005 Jul-Aug	15956235
Protective effects of etoricoxib, a selective inhibitor of cyclooxygenase-2, in experimental periodontitis in rats.	2005 Jun	15853965
Valdecoxib: assessment of cyclooxygenase-2 potency and selectivity.	2005 Mar	15494548
A liquid chromatography-mass spectrometry method for the quantification of both etoricoxib and valdecoxib in human plasma.	2005 Mar	15473012
The incidence of upper gastrointestinal adverse events in clinical trials of etoricoxib vs. non-selective NSAIDs: an updated combined analysis.	2005 May	15974563
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	15906586
Etoricoxib: a highly selective COX-2 inhibitor.	2005 May	15827069
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	15731291
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	16009523
Simultaneous quantitation of etoricoxib, salicylic acid, valdecoxib, ketoprofen, nimesulide and celecoxib in plasma by high-performance liquid chromatography with UV detection.	2006 Jan	16013036

Patents

Sample Use Guides

In Vivo Use Guide

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 `Wed Jul 05 23:16:43 UTC 2023` Edited by `admin` on `Wed Jul 05 23:16:43 UTC 2023`
Record UNII	WRX4NFY03R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETORICOXIB

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 [WHO-DD]

Common Name

English

ETORICOXIB [MART.]

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