ETORICOXIB

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 48 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 8297		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 8429	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
Rheumatoid arthritis 316 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Palliative	Approved 8429	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
Acute gouty arthritis 2 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Palliative	Approved 8429	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
Pain 614 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Primary	Approved 8429	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
Ankylosing spondylitis 33 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Arcoxia_6_12/WC500012804.pdf	Palliative	Approved 8429	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
Postoperative dental surgery pain 2 Sources: https://www.medicines.org.uk/emc/PIL.29146.latest.pdf	Primary	Approved 8429	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

Title	Date	PubMed
Preparation and novel reduction reactions of vinamidinium salts.	2001 Jan 12	11429907
Role of human liver cytochrome P4503A in the metabolism of etoricoxib, a novel cyclooxygenase-2 selective inhibitor.	2001 Jun	11353749
Dose proportionality of oral etoricoxib, a highly selective cyclooxygenase-2 inhibitor, in healthy volunteers.	2001 Oct	11583479
Etoricoxib.	2002	12466002
COX-2-selective inhibitors in the treatment of arthritis.	2002	12086290
Efficacy and tolerability profile of etoricoxib in patients with osteoarthritis: A randomized, double-blind, placebo and active-comparator controlled 12-week efficacy trial.	2002	12017209
Cox-2 inhibitors: today and tomorrow.	2002 Apr	12003372
A randomized, controlled, clinical trial of etoricoxib in the treatment of rheumatoid arthritis.	2002 Aug	12180720
Role of COX-2 inhibitors in the evolution of acute pain management.	2002 Jul	12204484
Randomised double blind trial of etoricoxib and indometacin in treatment of acute gouty arthritis.	2002 Jun 22	12077033
A multinational randomized, controlled, clinical trial of etoricoxib in the treatment of rheumatoid arthritis [ISRCTN25142273].	2002 May 22	12033987
Results of a randomized, dose-ranging trial of etoricoxib in patients with osteoarthritis.	2002 Sep	12209041
Analgesic efficacy of etoricoxib in primary dysmenorrhea: results of a randomized, controlled trial.	2003	12900528
COX-2: where are we in 2003?--distinction from NSAIDs becoming blurred.	2003	12723976
The second generation of COX-2 inhibitors: what advantages do the newest offer?	2003	12487621
[Coxibs: highly selective cyclooxygenase-2 inhibitors. Part II. Side effects].	2003 Apr	12868201
The role of cyclooxygenase selective inhibitors in the gastrointestinal tract.	2003 Dec	14602052
Absorption, metabolism, and excretion of etoricoxib, a potent and selective cyclooxygenase-2 inhibitor, in healthy male volunteers.	2003 Feb	12527704
Meloxicam and selective COX-2 inhibitors in the management of pain in the palliative care population.	2003 Jul-Aug	12911075
A literature review of the epidemiology and treatment of acute gout.	2003 Jun	12860487
Single- and multiple-dose pharmacokinetics of etoricoxib, a selective inhibitor of cyclooxygenase-2, in man.	2003 Mar	12638395
Gateways to clinical trials.	2003 May	12808477
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
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
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
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
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	14872504
Renal effects of etoricoxib and comparator nonsteroidal anti-inflammatory drugs in controlled clinical trials.	2004 Jan	14996519
Pharmacological characterisation of a rat model of incisional pain.	2004 Jan	14597606
Gateways to clinical trials.	2004 Jan-Feb	14988742
Gateways to clinical trials.	2004 Jul-Aug	15349141
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
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.	2005 Apr	15834452
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
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
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

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 `Fri Dec 15 15:48:16 GMT 2023` Edited by `admin` on `Fri Dec 15 15:48:16 GMT 2023`
Record UNII	WRX4NFY03R
Record Status	`Validated (UNII)`
Record Version

Download

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