Etoricoxib

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Etoricoxib are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Etoricoxib?

The molecule Etoricoxib presents a molecular formula of C18H15ClN2O2S and its IUPAC name is 5-chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine.

Etoricoxib (INN) is a nonsteroidal anti-inflammatory drug (NSAID) that selectively inhibits the cyclooxygenase-2 (COX-2) enzyme. It was developed by Merck & Co. and is marketed under the brand name Arcoxia..

Etoricoxib has analgesic, antipyretic, and antiinflammatory activity. It inhibits prostaglandin synthesis by inhibiting COX-2..

Etoricoxib has a half-life of 20–24 hours and is eliminated primarily by hepatic metabolism. It exists as tablets of 60, 90, and 120 mg..

The most common adverse effects are gastrointestinal, including nausea, vomiting, diarrhea, and abdominal pain. Other adverse effects include headache, dizziness, and rash..

Etoricoxib is contraindicated in pregnancy and in patients with a history of hypersensitivity to NSAIDs..

Etoricoxib was approved for use in the European Union in 2002 and in the United States in 2007..

3D structure

Cartesian coordinates

Geometry of Etoricoxib in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Etoricoxib MNJVRJDLRVPLFE-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Etoricoxib

 

Molecule descriptors

 
IUPAC name5-chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine
InChI codeInChI=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 KeyMNJVRJDLRVPLFE-UHFFFAOYSA-N
SMILESCc1ccc(-c2ncc(Cl)cc2-c2ccc(S(C)(=O)=O)cc2)cn1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 2,3'-Bipyridine, 5-chloro-6'-methyl-3-(4-(methylsulfonyl)phenyl)-
  • 2,3'-Bipyridine, 5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-
  • 202409-33-4
  • 409E334
  • 5-Chloro-3-(4-methanesulfonyl-phenyl)-6''''-methyl-[2,3'''']bipyridinyl
  • 5-Chloro-3-(4-methanesulfonyl-phenyl)-6''-methyl-[2,3'']bipyridinyl
  • 5-Chloro-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl
  • 5-Chloro-3-[4-(methylsulfonyl)phenyl]-2-(2-methyl-5-pyridinyl)pyridine
  • 5-Chloro-6'-methyl-3-(4-(methylsulfonyl)-phenyl)-2,3'-bipyridine
  • 5-Chloro-6'-methyl-3-(4-(methylsulfonyl)phenyl)-2,3'-bipyridine
  • 5-Chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridine
  • 5-chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridine
  • 5-chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine
  • 5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine
  • 5-chloro-6''-methyl-3-[4-(methylsulfonyl)phenyl]-2,3''-bipyridine
  • 5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine
  • 5CH
  • A848896
  • AB01275483-01
  • AC-29052
  • AMY30994
  • AS-17761
  • Algix
  • Arcoxia
  • BC164436
  • BCP06428
  • BDBM50072064
  • CCG-220639
  • CS-1047
  • D03710
  • DB-045133
  • DB01628
  • DSSTox_CID_26457
  • DSSTox_GSID_46457
  • DSSTox_RID_81631
  • EX-A2642
  • Etoricoxib
  • Etoricoxib (USAN/INN)
  • Etoricoxib- Bio-X
  • Etoricoxib; MK-663; MK-0663
  • Etoricoxibe
  • Etoxib
  • Etropain
  • F2173-0490
  • FT-0602793
  • FT-0668437
  • GTPL2896
  • HMS2090A05
  • HMS3713P20
  • HMS3885H14
  • HY-15321
  • J-013140
  • Kingcox
  • L-791,456
  • L-791456
  • L001141
  • L791456
  • MFCD06797512
  • MK 0663
  • MK 663
  • MK-0663
  • MK-0663;L-791456
  • MK-663
  • MK0663
  • NCGC00164578-01
  • NCGC00164578-02
  • Nucoxia
  • Q631202
  • SB18988
  • SR-05000001486
  • SR-05000001486-1
  • SR-05000001486-2
  • Tauxib
  • Torcoxia
  • Tox21 112206
  • WRX4NFY03R
  • etoricoxibum
  • s4651

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC579472
  • CAS-202409-33-4
  • UNII-WRX4NFY03R
  • AKOS016010125
  • BRD-K54770957-001-01-9
  • BRD-K54770957-001-02-7
  • DTXSID3046457
  • CHEMBL416146
  • CHEBI:6339
  • Tox21_112206
  • Tox21_112206_1
  • SCHEMBL4680

Physico-Chemical properties

IUPAC name5-chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine
Molecular formulaC18H15ClN2O2S
Molecular weight358.842
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity95.97
LogP5.3
Topological polar surface area68.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.