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| verifiedrevid = 451725338 | verifiedrevid = 451725338
| ImageFile = Clonixin.png | ImageFile = Clonixin.png
| ImageClass = skin-invert-image
| PIN = 2-(3-Chloro-2-methylanilino)pyridine-3-carboxylic acid | PIN = 2-(3-Chloro-2-methylanilino)pyridine-3-carboxylic acid
| OtherNames = Clonixic acid; CBA 93626<ref name="Clinical">{{cite journal|url=http://onlinelibrary.wiley.com/doi/10.1177/009127007101100508/abstract|title=Clonixin: A Clinical Evaluation of a New Oral Analgesic |journal=The Journal of Clinical Pharmacology and New Drugs |volume=11 |issue=5 |pages=371–377 |access-date=2015-05-21|doi=10.1177/009127007101100508|pmid=4935715 |year=1971 |last1=Finch |first1=Jay S. |last2=Dekornfeld |first2=Thomas J. |hdl=2027.42/67636 |s2cid=38883141 |hdl-access=free }}</ref> | OtherNames = Clonixic acid; CBA 93626<ref name="Clinical">{{cite journal|url=http://onlinelibrary.wiley.com/doi/10.1177/009127007101100508/abstract|title=Clonixin: A Clinical Evaluation of a New Oral Analgesic |journal=The Journal of Clinical Pharmacology and New Drugs |volume=11 |issue=5 |pages=371–377 |access-date=2015-05-21|doi=10.1177/009127007101100508|pmid=4935715 |year=1971 |last1=Finch |first1=Jay S. |last2=Dekornfeld |first2=Thomas J. |hdl=2027.42/67636 |s2cid=38883141 |hdl-access=free }}</ref>
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==Synthesis== ==Synthesis==
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==Clonixeril== ==Clonixeril==
The glyceryl ester of clonixin, clonixeril, is also an NSAID. It was prepared by a somewhat roundabout method. The glyceryl ester of clonixin, clonixeril, is also an NSAID. It was prepared by a somewhat roundabout method.
] ]
Clonixin was reacted with ] and ] to give '''2'''. Heating with ] and ] displaced the ] to produce ester '''3''', which was deblocked in ] to produce clonixeril ('''4'''). Clonixin was reacted with ] and ] to give '''2'''. Heating with ] and ] displaced the ] to produce ester '''3''', which was deblocked in ] to produce clonixeril ('''4''').


Latest revision as of 23:39, 10 January 2025

Nonsteroidal anti-inflammatory drug (NSAID)
Clonixin
Names
Preferred IUPAC name 2-(3-Chloro-2-methylanilino)pyridine-3-carboxylic acid
Other names Clonixic acid; CBA 93626
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.037.921 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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)Key: CLOMYZFHNHFSIQ-UHFFFAOYSA-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
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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:

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

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).
Prostanoid signaling modulators
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F2α)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthaseHQL-79
PGFSTooltip Prostaglandin F synthaseBimatoprost
PGI2STooltip Prostacyclin synthaseTranylcypromine
TXASTooltip Thromboxane A synthase
Others
See also
Receptor/signaling modulators
Leukotriene signaling modulators


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