Clonixin

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Clonixin
Clonixin.png
Names
IUPAC name
2-(3-chloro-2-methylanilino)pyridine-3-carboxylic acid
Other names
Clonixic acid; CBA 93626[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.037.921
KEGG
Properties
C13H11ClN2O2
Molar mass 262.69 g·mol−1
Pharmacology
per os
Pharmacokinetics:
Glucuronidation via UGT2B7
Legal status
  • US: Not sold in the U.S.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

Clonixin is a nonsteroidal anti-inflammatory drug (NSAID). It also has analgesic, antipyretic, and platelet-inhibitory actions. It is used primarily in the treatment of chronic arthritic conditions and certain soft tissue disorders associated with pain and inflammation.

Synthesis[edit]

Clonixin synthesis: M. H. Sherlock, N. Sperber, BE 679271 ; eidem, U.S. Patent 3,337,570 (1966, 1967 both to Schering).

Clonixeril[edit]

The glyceryl ester of clonixin, clonixeril, is also a NSAID. It was prepared by a somewhat roundabout method.

Clonixeril synthesis:[2][3]

Clonixin was reacted with chloroacetonitrile and triethylamine to give 2. Heating with potassium carbonate and glycerol actonide displaced the activating group to produce ester 3, which was deblocked in acetic acid to produce clonixeril (4).

See also[edit]

References[edit]

  1. ^ Finch, Jay S.; Dekornfeld, Thomas J. (1971). "Clonixin: A Clinical Evaluation of a New Oral Analgesic". The Journal of Clinical Pharmacology and New Drugs. 11 (5): 371–377. doi:10.1177/009127007101100508 (inactive 2019-03-15). Retrieved 2015-05-21.
  2. ^ M. H. Sherlock, ZA 6802185  (1968); Chem. Abstr., 70: 96640c (1969).
  3. ^ CH 534129  (1973); Chem. Abstr., 79: 18582g (1973).