droxicam

{{Short description|NSAID analgesic drug}}

{{Drugbox

| IUPAC_name = 2H,5H-1,3-Oxazino(5,6-c)(1,2)benzothiazine-2,4(3H)-dione, 5-methyl-3-(2-pyridinyl)-, 6,6-dioxide

| image = droxicam.svg

| alt = Skeletal formula of droxicam

| image_class = skin-invert-image

| width = 180

| image2 = Droxicam 3D spacefill.png

| image_class2 = bg-transparent

| width2 = 200

| alt2 = Space-filling model of the droxicam molecule

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| CAS_number = 90101-16-9

| ATC_prefix = M01

| ATC_suffix = AC04

| PubChem = 65679

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

| DrugBank =

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

| UNII = F24ADO1E2D

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

| KEGG = D07267

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 76133

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1213420

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 59108

| C=16 | H=11 | N=3 | O=5 | S=1

| smiles = CN1c2c(oc(=O)n(c2=O)c3ccccn3)-c4ccccc4S1(=O)=O

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C16H11N3O5S/c1-18-13-14(10-6-2-3-7-11(10)25(18,22)23)24-16(21)19(15(13)20)12-8-4-5-9-17-12/h2-9H,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OEHFRZLKGRKFAS-UHFFFAOYSA-N

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Droxicam is a non-steroidal anti-inflammatory drug of the oxicam class. A prodrug of piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.{{cite journal | vauthors = Jané F, Rodríguez de la Serna A | title = Droxicam: a pharmacological and clinical review of a new NSAID | journal = European Journal of Rheumatology and Inflammation | volume = 11 | issue = 4 | pages = 3–9 | date = 1991 | pmid = 1365488 | doi = | url = }}

Synthesis

:File:Droxicam synthesis (original).svg

When heated, phenyl pyridin-2-ylcarbamate (1) decomposes to 2-isocyanatopyridine (2) which reacts with the heterocyclic compound (3) to give droxicam.{{cite patent |country=US |number=4563452 |inventor=Jose M. Ribalta-Baro and Jordi F. Rigola-Constansa |title=Benzothiazine derivatives and their applications as medicinal products or as synthesis intermediates for medicinal products |status=patent |gdate=1992-07-21 |fdate=1990-07-31 |assign1=Laboratorios del Dr Esteve SA}}{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0164 |title=Droxicam |publisher=Thieme |access-date=2024-07-04}}{{cite web |url=https://www.chemdrug.com/article/8/3284/16419975.html |title=Droxicam |website=chemdrug.com |access-date=2024-07-04}}

References

{{Reflist}}

{{Anti-inflammatory and antirheumatic products}}

{{Prostanoid signaling modulators}}

Category:Dermatoxins

Category:Nonsteroidal anti-inflammatory drugs

Category:2-Pyridyl compounds

Category:Carbamates

Category:Sultams

{{musculoskeletal-drug-stub}}

{{analgesic-stub}}