Piroxicam

Piroxicam
Clinical data
Trade names	Feldene
AHFS/Drugs.com	Monograph
MedlinePlus	a684045
Pregnancy; category	C, D if used in the third trimester or near delivery;
Routes of; administration	PO
ATC code	M01AC01 (WHO) M02AA07 (WHO), S01BC06 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); US: WARNING; POM;
Pharmacokinetic data
Metabolism	4 to 10% renal
Elimination half-life	30 to 86 hours
Excretion	4 to 10% renal
Identifiers
	IUPAC name (8E)-8-[hydroxy-(pyridin-2-ylamino)methylidene]-; 9-methyl-10,10-dioxo-10λ6-thia-9-azabicyclo[4.4.0]; deca-1,3,5-trien-7-one;
CAS Number	36322-90-4 ;
PubChem CID	5280452;
DrugBank	DB00554 ;
ChemSpider	10442653 ;
UNII	13T4O6VMAM;
KEGG	D00127 ;
ChEBI	CHEBI:8249 ;
ChEMBL	ChEMBL527 ;
CompTox Dashboard (EPA)	DTXSID5021170 ;
ECHA InfoCard	100.048.144
Chemical and physical data
Formula	C15H13N3O4S
Molar mass	331.348 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC=2c1ccccc1S(=O)(=O)N(C)C=2C(=O)Nc3ccccn3;
	InChI InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20) ; Key:QYSPLQLAKJAUJT-UHFFFAOYSA-N ;
	(verify)

Piroxicam is a non-steroidal anti-inflammatory drug of the oxicam class used to relieve the symptoms of rheumatoid and osteoarthritis, primary dysmenorrhoea, postoperative pain; and act as an analgesic, especially where there is an inflammatory component. It is manufactured by Pfizer under the tradename Feldene, and is available in the UK, Spain, Portugal, Belgium, Australia, Italy, Brazil and the United States. It is also manufactured by Bosnalijek under the tradename Roxam, and is available in Eastern Europe, Africa, and the Middle East. In India, it is available by the tradename Dolonex. In Thailand it is available by the tradename Fasden. It is manufactured as a patch by SK Chemicals Co., Ltd. in Korea (www.skchemicals.com.cn) for use in China under the trade name "Trast"; the Chinese name (in Pinyin) is Biluoxikang Tiepian". In Pakistan it is available by the trade name Feldene.

It is also used in veterinary medicine to treat certain neoplasias expressing cyclooxygenase (COX) receptors, such as bladder, colon, and prostate cancers.

Other brand names for Piroxicam include "Arantil", "Brexidol", "Brexin", "Erazon", "Exipan", "Faxiden", "Felden", "Feldoral", "Flamexin", "Hawksone", "Hotemin", "Lubor", "Mobilis", "Pirox von ct", "Proponol", "Reumador", "Remox", "Roxam", "Sinartrol", "Toricam", "Tracam", "Ugesic", "Veral" and "Vurdon".

Mechanism of action

Piroxicam is an NSAID and, as such, is a non-selective COX inhibitor possessing both analgesic and antipyretic properties. It undergoes enterohepatic circulation.

Adverse effects

Piroxicam use can result in gastrointestinal toxicity, tinnitus, dizziness, headache, rash, and pruritus. The most severe adverse reactions are peptic ulceration, gastrointestinal bleeding, and severe skin reactions including Stevens–Johnson syndrome and toxic epidermal necrolysis. Approximately 30% of all patients receiving daily doses of 20 mg of piroxicam experience side effects.^[2]

In rare cases, piroxicam may cause skin to become more sensitive to sunlight.^[3]

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ New Zealand Medicines and Medical Devices Safety Authority. "Candyl Medicines datasheet". Retrieved 2006-09-10.
^ Mammen L, Schmidt CP (1995). "Photosensitivity reactions: a case report involving NSAIDs". Am Fam Physician. 52 (2): 575–9. PMID 7625330. {{cite journal}}: Unknown parameter |month= ignored (help)

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[2] New Zealand Medicines and Medical Devices Safety Authority. "Candyl Medicines datasheet". Retrieved 2006-09-10.

[3] Mammen L, Schmidt CP (1995). "Photosensitivity reactions: a case report involving NSAIDs". Am Fam Physician. 52 (2): 575–9. PMID 7625330. {{cite journal}}: Unknown parameter |month= ignored (help)

[1]

[2]

[3]

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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