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]

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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