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	17737-65-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76200^N[???]
ChEMBL	ChEMBL1332971^N
ChemSpider	26711^N
ECHA InfoCard	100.037.921
KEGG	D03555^Y
PubChem CID	28718
UNII	V7DXN0M42R^Y
CompTox Dashboard (EPA)	DTXSID2046121
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
Routes of administration	per os
Pharmacokinetics:
Metabolism	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 ^YN ?) 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 an 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 acetonide displaced the activating group to produce ester 3, which was deblocked in acetic acid to produce clonixeril (4).

See also

• Flunixin

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. hdl:2027.42/67636. PMID 4935715. S2CID 38883141. 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).