6-Hydroxymethyletoricoxib

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 6-Hydroxymethyletoricoxib are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 6-Hydroxymethyletoricoxib?

The molecule 6-Hydroxymethyletoricoxib presents a molecular formula of C18H15ClN2O3S and its IUPAC name is [5-[5-chloro-3-(4-methylsulfonylphenyl)pyridin-2-yl]pyridin-2-yl]methanol.

6-Hydroxymethyletoricoxib is a molecule of the drug etoricoxib. It is a nonsteroidal anti-inflammatory drug (NSAID) of the coxib class. It works by inhibiting the enzyme cyclooxygenase (COX), which participes in the production of prostaglandins, substances that play a key role in inflammation and pain..

6-Hydroxymethyletoricoxib was first synthesized in 1992 and patented in 1996. It was approved for medical use in the United States in 2002. It exists as a generic medication..

Medical uses.

6-Hydroxymethyletoricoxib is used for the treatment of osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis. It is also used for the relief of pain and inflammation associated with acute gouty arthritis..

Side effects.

The most common side effects of 6-hydroxymethyletoricoxib are headache, diarrhea, and abdominal pain. Other side effects include dizziness, rash, and upper respiratory tract infections..

6-Hydroxymethyletoricoxib can cause serious side effects, including:.

* gastrointestinal bleeding.

* ulcers.

* perforation of the stomach or intestines.

* kidney problems.

* liver problems.

* heart attack.

* stroke.

Serious side effects are more likely in people who are elderly or have heart disease..

6-Hydroxymethyletoricoxib should not be used by people with a history of gastrointestinal bleeding or ulcers. It should also be used with caution in people with kidney or liver disease, high blood pressure, or a history of heart disease..

Pregnancy and breastfeeding.

6-Hydroxymethyletoricoxib is not recommended for use during pregnancy. It is not known if it is excreted in breast milk..

3D structure

Cartesian coordinates

Geometry of 6-Hydroxymethyletoricoxib in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

6-Hydroxymethyletoricoxib SCVWZQQMIZJGJY-UHFFFAOYSA-N chemical compound 2D structure molecule svg
6-Hydroxymethyletoricoxib

 

Molecule descriptors

 
IUPAC name[5-[5-chloro-3-(4-methylsulfonylphenyl)pyridin-2-yl]pyridin-2-yl]methanol
InChI codeInChI=1S/C18H15ClN2O3S/c1-25(23,24)16-6-3-12(4-7-16)17-8-14(19)10-21-18(17)13-2-5-15(11-22)20-9-13/h2-10,22H,11H2,1H3
InChI KeySCVWZQQMIZJGJY-UHFFFAOYSA-N
SMILESCS(=O)(=O)c1ccc(-c2cc(Cl)cnc2-c2ccc(CO)nc2)cc1

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)-6'-methanol, 5-chloro-3-(4-(methylsulfonyl)phenyl)-
  • (5-(5-Chloranyl-3-(4-methylsulfonylphenyl)pyridin-2-yl)pyridin-2-yl)methanol
  • (5-Chloro-3-(4-(methylsulfonyl)phenyl)-[2,3'-bipyridin]-6'-yl)methanol
  • (5-Chloro-3-(4-(methylsulfonyl)phenyl)-[2,3'-bipyridin]-6'-yl)methanol (Etoricoxib Impurity)
  • 3-(4-Mesylphenyl)-5-chloro-2,3'-bipyridine-6'-methanol
  • 349536-41-0
  • 5-Chloro-3-(4-(methylsulfonyl)phenyl)(2,3'-bipyridine)-6'-methanol
  • 6 inverted exclamation mark -Desmethyl-6 inverted exclamation mark -methylhydroxy Etoricoxib
  • 6'-Desmethyl-6'-methylhydroxy Etoricoxib
  • 6'-Hydroxymethyl etoricoxib
  • 6'-Hydroxymethyl-etoricoxib
  • 6-Hydroxymethyletoricoxib
  • 8A0E1G55M9
  • BDBM50099001
  • CS-0255268
  • Etoricoxib impurity 2
  • [5-Chloro-3-(4-methanesulfonyl-phenyl)-[2,3'']bipyridinyl-6''-yl]-methanol
  • [5-[5-chloro-3-(4-methylsulfonylphenyl)pyridin-2-yl]pyridin-2-yl]methanol
  • [5-[5-chloro-3-(4-methylsulonylphenyl)pyridin-2-yl]pyridin-2-yl]methanol
  • {5-[5-chloro-3-(4-methanesulfonylphenyl)pyridin-2-yl]pyridin-2-yl}methanol

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • UNII-8A0E1G55M9
  • CHEMBL10042
  • CHEBI:187856

Physico-Chemical properties

IUPAC name[5-[5-chloro-3-(4-methylsulfonylphenyl)pyridin-2-yl]pyridin-2-yl]methanol
Molecular formulaC18H15ClN2O3S
Molecular weight374.841
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity97.14
LogP4.4
Topological polar surface area88.5

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.