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Clonixin

From Wikipedia, the free encyclopedia
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[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.037.921Edit this at Wikidata
KEGG
UNII
  • 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
  • O=C(O)C1=CC=CN=C1NC2=C(C)C(Cl)=CC=C2
Properties
C13H11ClN2O2
Molar mass262.69 g·mol−1
Pharmacology
per os
Pharmacokinetics:
Glucuronidation via UGT2B7
Legal status
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Clonixin is anonsteroidal anti-inflammatory drug (NSAID). It also hasanalgesic,antipyretic, andplatelet-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 toSchering).

Clonixeril

[edit]

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 withchloroacetonitrile andtriethylamine to give2. Heating withpotassium carbonate andglycerol acetonide displaced theactivating group to produce ester3, which was deblocked inacetic 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.hdl:2027.42/67636.PMID 4935715.S2CID 38883141. Retrieved2015-05-21.
  2. ^M. H. Sherlock,ZA 6802185  (1968); Chem. Abstr., 70: 96640c (1969).
  3. ^CH 534129  (1973); Chem. Abstr., 79: 18582g (1973).
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 (F)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 synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others


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