Droxicam

Droxicam
Clinical data
ATC code	M01AC04 (WHO) ;
Identifiers
	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;
CAS Number	90101-16-9;
PubChem CID	65679;
ChemSpider	59108 ;
UNII	F24ADO1E2D;
KEGG	D07267 ;
ChEBI	CHEBI:76133 ;
ChEMBL	ChEMBL1213420 ;
CompTox Dashboard (EPA)	DTXSID70238035 ;
Chemical and physical data
Formula	C16H11N3O5S
Molar mass	357.34 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1c2c(oc(=O)n(c2=O)c3ccccn3)-c4ccccc4S1(=O)=O;
	InChI InChI=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 ; Key:OEHFRZLKGRKFAS-UHFFFAOYSA-N ;

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.^[1]

Synthesis

When heated, phenyl pyridin-2-ylcarbamate (1) decomposes to 2-isocyanatopyridine (2) which reacts with the heterocyclic compound (3) to give droxicam.^[2]^[3]^[4]

References

^ Jané F, Rodríguez de la Serna A (1991). "Droxicam: a pharmacological and clinical review of a new NSAID". European Journal of Rheumatology and Inflammation. 11 (4): 3–9. PMID 1365488.
^ US patent 4563452, Jose M. Ribalta-Baro and Jordi F. Rigola-Constansa, "Benzothiazine derivatives and their applications as medicinal products or as synthesis intermediates for medicinal products", issued 1992-07-21, assigned to Laboratorios del Dr Esteve SA
^ "Droxicam". Thieme. Retrieved 2024-07-04.
^ "Droxicam". chemdrug.com. Retrieved 2024-07-04.

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[pmid1365488-1] Jané F, Rodríguez de la Serna A (1991). "Droxicam: a pharmacological and clinical review of a new NSAID". European Journal of Rheumatology and Inflammation. 11 (4): 3–9. PMID 1365488.

[2] US patent 4563452, Jose M. Ribalta-Baro and Jordi F. Rigola-Constansa, "Benzothiazine derivatives and their applications as medicinal products or as synthesis intermediates for medicinal products", issued 1992-07-21, assigned to Laboratorios del Dr Esteve SA

[3] "Droxicam". Thieme. Retrieved 2024-07-04.

[4] "Droxicam". chemdrug.com. Retrieved 2024-07-04.

[1]

Clinical data


ATC code	M01AC04 (WHO)
Identifiers
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
CAS Number	90101-16-9
PubChem CID	65679
ChemSpider	59108^Y
UNII	F24ADO1E2D
KEGG	D07267^Y
ChEBI	CHEBI:76133^Y
ChEMBL	ChEMBL1213420^Y
CompTox Dashboard (EPA)	DTXSID70238035
Chemical and physical data
Formula	C₁₆H₁₁N₃O₅S
Molar mass	357.34 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1c2c(oc(=O)n(c2=O)c3ccccn3)-c4ccccc4S1(=O)=O
InChI InChI=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^Y Key:OEHFRZLKGRKFAS-UHFFFAOYSA-N^Y