Piroxicam

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Piroxicam
Piroxicam.svg
Piroxicam molecule
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, "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"
AHFS/Drugs.com monograph
MedlinePlus a684045
Pregnancy cat. C (AU) C (US) D, if used during the 3rd trimester; may cause ductus arteriosus.
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Protein binding 99.3%
Metabolism 4 to 10% renal
Half-life 50 hours
Excretion Urine, faeces
Identifiers
CAS number 36322-90-4 YesY
ATC code M01AC01 M02AA07, S01BC06
PubChem CID 5280452
DrugBank DB00554
ChemSpider 10442653 YesY
UNII 13T4O6VMAM YesY
KEGG D00127 YesY
ChEBI CHEBI:8249 YesY
ChEMBL CHEMBL527 YesY
Chemical data
Formula C15H13N3O4S 
Mol. mass 331.348 g/mol
 YesY (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 Canada, 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 in Korea for use in China under the trade name Trast. In Pakistan it is available by the trade name Feldene.

The first study of theraputic use in humans was reported in 1977 [1]

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


Mechanism of action[edit]

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[edit]

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[edit]

  1. ^ Weintraub M, Jacox RF, Angevine CD, Atwater EC (1977). "Piroxicam (CP 16171) in rheumatoid arthritis: a controlled clinical trial with novel assessment techniques". Journal of Rheumatology. 4 (4): 393–404. 
  2. ^ New Zealand Medicines and Medical Devices Safety Authority. "Candyl Medicines datasheet". Retrieved 2006-09-10. 
  3. ^ Mammen L, Schmidt CP (August 1995). "Photosensitivity reactions: a case report involving NSAIDs". Am Fam Physician 52 (2): 575–9. PMID 7625330.