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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 of ETORICOXIB

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

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
Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2.
2001 Feb
Preparation and novel reduction reactions of vinamidinium salts.
2001 Jan 12
Etoricoxib.
2002
Development and clinical application of COX-2-selective inhibitors for the treatment of osteoarthritis and rheumatoid arthritis.
2002
Efficacy and tolerability profile of etoricoxib in patients with osteoarthritis: A randomized, double-blind, placebo and active-comparator controlled 12-week efficacy trial.
2002
Gateways to clinical trials.
2002 Dec
Gateways to Clinical Trials. June 2002.
2002 Jun
The second generation of COX-2 inhibitors: what advantages do the newest offer?
2003
The gastrointestinal safety of the COX-2 selective inhibitor etoricoxib assessed by both endoscopy and analysis of upper gastrointestinal events.
2003 Aug
Gateways to clinical trials.
2003 Jan-Feb
Meloxicam and selective COX-2 inhibitors in the management of pain in the palliative care population.
2003 Jul-Aug
Characterization of etoricoxib, a novel, selective COX-2 inhibitor.
2003 Jun
Single- and multiple-dose pharmacokinetics of etoricoxib, a selective inhibitor of cyclooxygenase-2, in man.
2003 Mar
Gateways to clinical trials.
2003 May
Etoricoxib in the treatment of chronic pain.
2003 May
Clinical pharmacology of selective COX-2 inhibitors.
2003 May-Aug
Etoricoxib reduced pain and disability and improved quality of life in patients with chronic low back pain: a 3 month, randomized, controlled trial.
2004
[Pharmacology and classification of cyclooxygenase inhibitors].
2004 Apr
[Comparison of preemptive analgesia efficacy between etoricoxib and rofecoxib in ambulatory gynecological surgery].
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
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
Gateways to clinical trials.
2004 Nov
Gateways to clinical trials.
2004 Sep
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
Relative thromboembolic risks associated with COX-2 inhibitors.
2005 Jul-Aug
A liquid chromatography-mass spectrometry method for the quantification of both etoricoxib and valdecoxib in human plasma.
2005 Mar
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
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 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
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 [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
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
WHO-VATC QM01AH05
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
Code System Code Type Description
IUPHAR
2896
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
USAN
MM-46
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
SMS_ID
100000078581
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
DRUG CENTRAL
1113
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL416146
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
PUBCHEM
123619
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
MERCK INDEX
m5200
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY Merck Index
EVMPD
SUB16429MIG
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
CAS
202409-33-4
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
INN
8082
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
NCI_THESAURUS
C52188
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
CHEBI
6339
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
WIKIPEDIA
ETORICOXIB
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
RXCUI
307296
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY RxNorm
FDA UNII
WRX4NFY03R
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID3046457
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
DRUG BANK
DB01628
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
MESH
C422649
Created by admin on Fri Dec 15 15:48:16 GMT 2023 , Edited by admin on Fri Dec 15 15:48:16 GMT 2023
PRIMARY
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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