ChemFOnt: Showing chemical card for Etoricoxib (CFc000009827)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:05 UTC

Chemfont ID

CFc000009827

Molecule Identification

Common Name

Etoricoxib

Definition

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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridine	ChEBI
5-Chloro-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl	ChEBI
5-Chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridine	ChEBI
Etoricoxibum	ChEBI
L791456	ChEBI
5-Chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulphonyl)phenyl)pyridine	Generator
5-Chloro-3-(4-methanesulphonyl-phenyl)-6'-methyl-[2,3']bipyridinyl	Generator
5-Chloro-6'-methyl-3-(p-(methylsulphonyl)phenyl)-2,3'-bipyridine	Generator
MK-663	HMDB
Arcoxia	HMDB

Chemical Formula

C₁₈H₁₅ClN₂O₂S

Average Molecular Weight

358.842

Monoisotopic Molecular Weight

358.054276131

IUPAC Name

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

Traditional Name

etoricoxib

CAS Registry Number

202409-33-4

SMILES

CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O

InChI Identifier

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

InChI Key

MNJVRJDLRVPLFE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Bipyridines and oligopyridines

Direct Parent

Bipyridines and oligopyridines

Alternative Parents

Substituents

Bipyridine
3-phenylpyridine
Benzenesulfonyl group
Methylpyridine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Sulfone
Sulfonyl
Heteroaromatic compound
Azacycle
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfone (CHEBI:6339 )
organochlorine compound (CHEBI:6339 )
bipyridines (CHEBI:6339 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015565)
Membrane (HMDB: HMDB0015565)

Source

Exogenous

Exogenous (HMDB: HMDB0015565)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Etoricoxib Action Pathway (PathBank: SMP0000695)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0033 g/L	ALOGPS
logP	3.7	ALOGPS
logP	2.79	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	19.69	ChemAxon
pKa (Strongest Basic)	4.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.04 m³·mol⁻¹	ChemAxon
Polarizability	36.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon