Clonixin

Clonixin
Names
Preferred IUPAC name
2-(3-Chloro-2-methylanilino)pyridine-3-carboxylic acid
Other names
Clonixic acid; CBA 93626[1]
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.037.921
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KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C13H11ClN2O2/c1-8-10(14)5-2-6-11(8)16-12-9(13(17)18)4-3-7-15-12/h2-7H,1H3,(H,15,16)(H,17,18) ☒N
    Key: CLOMYZFHNHFSIQ-UHFFFAOYSA-N ☒N
  • InChI=1/C13H11ClN2O2/c1-8-10(14)5-2-6-11(8)16-12-9(13(17)18)4-3-7-15-12/h2-7H,1H3,(H,15,16)(H,17,18)
    Key: CLOMYZFHNHFSIQ-UHFFFAOYAG
SMILES
  • O=C(O)C1=CC=CN=C1NC2=C(C)C(Cl)=CC=C2
Properties
Chemical formula
 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).
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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

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

Clonixeril

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

References

  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 31 October 2021). PMID 4935715. Retrieved 2015-05-21.{{cite journal}}: CS1 maint: DOI inactive as of October 2021 (link)
  2. ↑ M. H. Sherlock, ZA 6802185 (1968); Chem. Abstr., 70: 96640c (1969).
  3. ↑ CH 534129 (1973); Chem. Abstr., 79: 18582g (1973).


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