Piroxicam

Systematic (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
Clinical data
Trade names	Feldene
AHFS/Drugs.com	monograph
MedlinePlus	a684045
Pregnancy cat.	C, D if used in the third trimester or near delivery
Legal status	POM
Routes	PO
Pharmacokinetic data
Metabolism	4 to 10% renal
Half-life	30 to 86 hours
Excretion	4 to 10% renal
Identifiers
CAS number	36322-90-4 Y
ATC code	M01AC01 M02AA07, S01BC06
PubChem	CID 5280452
DrugBank	DB00554
ChemSpider	10442653 Y
UNII	13T4O6VMAM Y
KEGG	D00127 Y
ChEBI	CHEBI:8249 Y
ChEMBL	CHEMBL527 Y
Chemical data
Formula	C15H13N3O4S
Mol. mass	331.348 g/mol
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) Y Key:QYSPLQLAKJAUJT-UHFFFAOYSA-N Y
Y (what is this?)  (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, 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".

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 "Brexidol", "Brexin", "Erazon", "Exipan", "Faxiden", "Felden", "Feldoral", "Flamexin", "Hotemin", "Lubor", "Mobilis", "Pirox von ct", "Proponol", "Reumador", "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.^[1]

In rare cases, piroxicam may cause skin to become more sensitive to sunlight.^[2]

  References