Clonixin

Clonixin

Names
IUPAC name 2-(3-chloro-2-methylanilino)pyridine-3-carboxylic acid
Other names Clonixic acid; CBA 93626[1]
Identifiers
CAS Number	17737-65-4 Y
ChEBI	CHEBI:76200 N[???]
ChEMBL	ChEMBL1332971 N
ChemSpider	26711 N
Jmol interactive 3D	Image
KEGG	D03555 Y
PubChem	28718
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
Legal status	US: Not sold in the U.S.
Routes of administration	per os
Pharmacokinetics:
Metabolism	Glucuronidation via UGT2B7
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Clonixin is a non-steroidal anti-inflammatory drug. 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

• Flunixin
• Clonixeril

References