Piroxicam

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Piroxicam
Piroxicam2DACS.svg
Piroxicam molecule
Systematic (IUPAC) name
4-Hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
Clinical data
Trade namesBrexidol, Candyl, Feldene and many others.
AHFS/Drugs.commonograph
MedlinePlusa684045
Pregnancy cat.C (AU) C (US) D (US), if used during the 3rd trimester, as it may cause ductus arteriosus.
Legal statusPrescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
RoutesOral
Pharmacokinetic data
Protein binding99%[1]
MetabolismLiver-mediated hydroxylation and glucuronidation[1]
Half-life50 hours[1]
ExcretionUrine, faeces
Identifiers
CAS number36322-90-4 YesY
ATC codeM01AC01 M02AA07, S01BC06
PubChemCID 5280452
DrugBankDB00554
ChemSpider10442653 YesY
UNII13T4O6VMAM YesY
KEGGD00127 YesY
ChEBICHEBI:8249 YesY
ChEMBLCHEMBL527 YesY
Chemical data
FormulaC15H13N3O4S 
Mol. mass331.348 g/mol
 YesY (what is this?)  (verify)
 
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Piroxicam
Piroxicam2DACS.svg
Piroxicam molecule
Systematic (IUPAC) name
4-Hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
Clinical data
Trade namesBrexidol, Candyl, Feldene and many others.
AHFS/Drugs.commonograph
MedlinePlusa684045
Pregnancy cat.C (AU) C (US) D (US), if used during the 3rd trimester, as it may cause ductus arteriosus.
Legal statusPrescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
RoutesOral
Pharmacokinetic data
Protein binding99%[1]
MetabolismLiver-mediated hydroxylation and glucuronidation[1]
Half-life50 hours[1]
ExcretionUrine, faeces
Identifiers
CAS number36322-90-4 YesY
ATC codeM01AC01 M02AA07, S01BC06
PubChemCID 5280452
DrugBankDB00554
ChemSpider10442653 YesY
UNII13T4O6VMAM YesY
KEGGD00127 YesY
ChEBICHEBI:8249 YesY
ChEMBLCHEMBL527 YesY
Chemical data
FormulaC15H13N3O4S 
Mol. mass331.348 g/mol
 YesY (what is this?)  (verify)

Piroxicam /pˈrɒksɪˌkæm/ (INN, BAN, USAN, AAN; in some countries it is spelt piroksikam or piroxikam) is a non-steroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve the symptoms of painful, inflammatory conditions like arthritis.[1][2] Piroxicam works by preventing the production of a certain type of body chemical called prostaglandins which are involved in the mediation of pain, stiffness, tenderness and swelling.[1] The medicine is available as capsules, tablets and (not in all countries) as a prescription-free gel 0.5%.[3] It is also available in a betadex formulation, which allows a more rapid absorption of piroxicam from the digestive tract.[1]

It is manufactured by Pfizer under the tradename Feldene, and is available in Canada, the United Kingdom, Spain, Portugal, Belgium, Australia, Italy, Brazil, Indonesia, Pakistan and the United States, and under the tradename Brexidol in the Scandinavian countries.[1] It is also manufactured by Bosnalijek under the tradename Roxam, and is available in Eastern Europe including Russia, Africa, and the Middle East. In India, it is available by the tradename Dolonex, whereas in Thailand it is available by the tradename Fasden.[1] It is manufactured as a patch in Korea for use in China under the trade name Trast.[1]

The first study of therapeutic use in humans was reported in 1977.[4]

Medical uses[edit]

It used in the treatment of rheumatoid and osteoarthritis, primary dysmenorrhoea, postoperative pain; and act as an analgesic, especially where there is an inflammatory component.[1] The European Medicines Agency issued a review of its use in 2007 and recommended that its use be limited to the treatment of chronic inflammatory conditions, as it only in these circumstances that its risk-benefit ratio proves to be favourable.[3][5]

Adverse effects[edit]

As with other NSAIDs the principal side effects include: digestive complaints like nausea, discomfort, diarrhoea and bleeds or ulceration of the stomach, as well as headache, dizziness, nervousness, depression, drowsiness, insomnia, vertigo, hearing disturbances (such as tinnitus), high blood pressure, oedema, light sensitivity, skin reactions (including, albeit rarely, Stevens-Johnson syndrome and toxic epidermal necrolysis) and rarely, kidney failure, pancreatitis, liver damage, visual disturbances, pulmonary eosinophilia and alveolitis.[3] Compared to other NSAIDs it is more prone to causing GI disturbances and serious skin reactions.[3]

Mechanism of action[edit]

Piroxicam is an NSAID and, as such, is a non-selective COX inhibitor possessing both analgesic and antipyretic properties.[3]

Society and culture[edit]

Brand names[edit]

They include: Arantil, Brexidol, Brexin, Erazon, Exipan, Faxiden, Felden, Feldene, Feldoral, Flamexin, Hawksone, Hotemin, Lubor, Mobilis, Novo-Pirocam, Pirox von ct, Proponol, Reumador, Remox, Roxam, Sinartrol, Toricam, Tracam, Ugesic, Veral and Vurdon.


References[edit]

  1. ^ a b c d e f g h i j Brayfield, A, ed. (14 January 2014). "Piroxicam". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 24 June 2014. 
  2. ^ TGA Approved Terminology for Medicines, Section 1 – Chemical Substances (PDF). Therapeutic Goods Administration, Department of Health and Ageing, Australian Government. July 1999. p. 97. 
  3. ^ a b c d e Joint Formulary Committee (2013). British National Formulary (BNF) (65 ed.). London, UK: Pharmaceutical Press. pp. 665, 673–674. ISBN 978-0-85711-084-8.  edit
  4. ^ 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. 
  5. ^ "COMMITTEE FOR MEDICINAL PRODUCTS FOR HUMAN USE (CHMP) OPINION FOLLOWING AN ARTICLE 31(2) REFERRAL PIROXICAM CONTAINING MEDICINAL PRODUCTS" (PDF). European Medicines Agency. London, UK: European Medicines Agency. 20 September 2007. Retrieved 24 June 2014.