5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine

• ChemBase ID: 1404
• Molecular Formular: C18H15ClN2O2S
• Molecular Mass: 358.8419
• Monoisotopic Mass: 358.05427641
• SMILES: Clc1cc(c2ccc(S(=O)(=O)C)cc2)c(nc1)c1ccc(nc1)C
• Canonical SMILES: Clc1cnc(c(c1)c1ccc(cc1)S(=O)(=O)C)c1ccc(nc1)C
• InChI: 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
• InChIKey: MNJVRJDLRVPLFE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine
• IUPAC Traditional name: etoricoxib
• Brand Name: Arcoxia; Nucoxia; Tauxib; Algix
• Synonyms: 5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine; 5-Chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine; Algix; Arcoxia; Etobrix; Etocox; Etoxib; Etropain; Kingcox; MK 0663; MK 663; Tauxib; Torcoxia; etoricoxib; MK-663; Etoricoxib

Database IDs

• CAS Number: 202409-33-4
• PubChem SID: 160964864; 46504505
• PubChem CID: 123619
• CHEBI ID: 6339
• ATC CODE: M01AH05
• CHEMBL: 416146
• Chemspider ID: 110209
• DrugBank ID: DB01628
• KEGG ID: D03710
• Unique Ingredient Identifier: WRX4NFY03R
• Wikipedia Title: Etoricoxib

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.693102
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.6881886
• LogD (pH = 7.4): 2.7924058
• Log P: 2.7939253
• Molar Refractivity: 95.0445 cm^3
• Polarizability: 40.067413 Å^3
• Polar Surface Area: 59.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.7
• LOG S: -5.04
• Solubility (Water): 3.28e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 135-138°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 100%
• Excretion: Renal (70%) and fecal (20%)
• Half Life: 22 hours
• Metabolism: Hepatic, CYP extensively involved (mainly CYP3A4)
• Protein Bound: 92%
• Legal Status: POM (UK)
• Pregnancy Category: Not recommended

DETAILS

DrugBank - DB07166

Drug information: experimental

DrugBank - DB01628

• Drug Groups: approved; investigational
• Description: Etoricoxib is a new COX-2 selective inhibitor. Current therapeutic indications are: treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout. Like any other COX-2 selective inhibitor, Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme (COX-2). This reduces the generation of prostaglandins (PGs) from arachidonic acid.
• Indication: For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout.
• Pharmacology: Etoricoxib is a COX-2 selective inhibitor (approximately 106 times more selective for COX-2 inhibition over COX-1). Currently it is approved in more than 60 countries worldwide but not in the US, where the Food and Drug Administration (FDA) require additional safety and efficacy data for etoricoxib before it will issue approval.
• Toxicity: This reduced activity is the cause of reduced gastrointestinal toxicity, as demonstrated in several large clinical trials performed with different COXIB (see below links on NEJM and The Lancet). Some clinical trials and meta-analysis showed that treatment with COXIB lead to increased incidence of cardiovascular adverse events compared to placebo
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, primarily via CYP3A4.
• Absorption: Bioavailability is 100% following oral administration.
• Half Life: 22 hours
• Protein Binding: 92%
• External Links: Wikipedia

Toronto Research Chemicals - E934100

A specific inhibitor of COX-2 .

REFERENCES

• McGeer, P.L., et al.: Exp. Gerontol., 37, 925 (2002)
• Chenevard, R., et al.: Circulation, 107, 405 (2003)