Clonixin

{{Short description|Nonsteroidal anti-inflammatory drug (NSAID)}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451725338

| ImageFile = Clonixin.png

| ImageClass = skin-invert-image

| PIN = 2-(3-Chloro-2-methylanilino)pyridine-3-carboxylic acid

| OtherNames = Clonixic acid; CBA 93626{{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 }}

|Section1={{Chembox Identifiers

| Abbreviations =

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 17737-65-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = V7DXN0M42R

| PubChem = 28718

| SMILES = O=C(O)C1=CC=CN=C1NC2=C(C)C(Cl)=CC=C2

| MeSHName =

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 26711

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1332971

| 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)

| InChIKey = CLOMYZFHNHFSIQ-UHFFFAOYAG

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = CLOMYZFHNHFSIQ-UHFFFAOYSA-N

| ChEBI_Ref = {{ebicite|changed|???}}

| ChEBI = 76200

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D03555

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|Section2={{Chembox Properties

| C=13 | H=11 | Cl=1 | N=2 | O=2

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|Section3={{Chembox Pharmacology

| AdminRoutes = per os

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| Metabolism = Glucuronidation via UGT2B7

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| Legal_status =

| Legal_US = Not sold in the U.S.

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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

Clonixeril

The glyceryl ester of clonixin, clonixeril, is also an NSAID. It was prepared by a somewhat roundabout method.

File:Clonixeril synthesis.svg

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