Piroxicam

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Piroxicam

Clinical data

Trade names Feldene and many others[1]

AHFS/Drugs.com Monograph

MedlinePlus a684045

Pregnancy  AU: C

category  US: C (Risk not ruled out)

 D (US), if used during the 3rd trimester, as it may

cause ductus arteriosus.

Routes of Oral
administration

ATC code  M01AC01 (WHO) M02AA07 (WHO), S01BC06 (WHO)

Legal status

Legal status  AU: S4 (Prescription only)

 CA: ℞-only
  UK: POM (Prescription only)

 US: ℞-only

Pharmacokinetic data

Protein binding 99%[2]

Metabolism Liver-mediated hydroxylation and glucuronidation[2]

Elimination half- 50 hours[2]

life

Excretion Urine, faeces

Identifiers

IUPAC name[show]

CAS Number  36322-90-4

PubChem CID 54676228

IUPHAR/BPS  7273

DrugBank  DB00554

ChemSpider  10442653

UNII  13T4O6VMAM

KEGG  D00127

ChEBI  CHEBI:8249

ChEMBL  ChEMBL527

ECHA InfoCard 100.048.144

Chemical and physical data

Formula C15H13N3O4S

Molar mass 331.348 g/mol

3D model  Interactive image

(JSmol)

SMILES[show]

InChI[show]

(verify)

Piroxicam /paɪˈrɒksɪˌkæm/ (INN, BAN, USAN, AAN; in some countries it is spelled piroksikam or
piroxikam) is a nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve
the symptoms of painful inflammatory conditions like arthritis.[2][3]Piroxicam works by preventing
the production of endogenous prostaglandins which are involved in the mediation of pain,
stiffness, tenderness and swelling.[2] The medicine is available as capsules, tablets and (not in all
countries) as a prescription-free gel 0.5%.[4] It is also available in a betadex formulation, which
 allows a more rapid absorption of piroxicam from the digestive tract.[2] Piroxicam is one of the few
NSAIDs that can be given parenteral routes.
It was originally brought to market by Pfizer under the tradename Feldene in 1980, became
generic in 1992,[5] and is marketed worldwide under many brandnames.[1]

Contents

 1Medical uses
 2Adverse effects
 3Mechanism of action
 4Chemical properties
 5History
 6See also
 7References

Medical uses[edit]
It is used in the treatment of rheumatoid and osteoarthritis, primary dysmenorrhoea,
postoperative pain; and act as an analgesic, especially where there is
an inflammatory component.[2] 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 is only in these circumstances that its risk-benefit ratio proves to be
favourable.[4][6]

Adverse effects[edit]
See also: Nonsteroidal anti-inflammatory drug
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.[4] Compared to other NSAIDs it is more prone to causing
gastrointestinal disturbances and serious skin reactions.[4]

Mechanism of action[edit]
See also: Nonsteroidal anti-inflammatory drug
Piroxicam is an NSAID and, as such, is a non-selective COX inhibitor possessing both analgesic
and antipyretic properties.[4]

Chemical properties[edit]
Piroxicam exists as enol tautomer in organic solvents and as zwitterionic form in water.[7]

History[edit]
The project that produced piroxicam began in 1962 at Pfizer; the first clinical trial results were
reported in 1977, and the product launched in 1980 under the brand name "Feldene".[5][8] Major
patents expired in 1992[5] and the drug is marketed worldwide under many brandnames.[1]

See also[edit]
 Meloxicam
 Isoxicam
 Lornoxicam

References[edit]
1. ^ Jump up to:a b c Drugs.com Drugs.com international listings for piroxicam Page accessed July 3,
2015
2. ^ Jump up to:a b c d e f g Brayfield, A, ed. (14 January 2014). "Piroxicam". Martindale: The Complete
Drug Reference. London, UK: Pharmaceutical Press. Retrieved 24 June 2014.
3. ^ "TGA Approved Terminology for Medicines, Section 1 – Chemical Substances" (PDF).
Therapeutic Goods Administration, Department of Health and Ageing, Australian Government.
July 1999: 97.
4. ^ Jump up to: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.
5. ^ Jump up to:a b c Lombardino JG, Lowe JA 3rd. The role of the medicinal chemist in drug
discovery--then and now. Nat Rev Drug Discov. 2004 Oct;3(10):853-62. PMID 15459676.
See: [1] Box 1: Discovery of piroxicam (1962–1980)]
6. ^ "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.
7. ^ Ivanova D, Deneva V, Nedeltcheva D, Kamounah FS, Gergov G, Hansen PE, Kawauchi S,
Antonov L (2015). "Tautomeric transformations of piroxicam in solution: a combined experimental
and theoretical study". RSC Advances. 5: 31852–31860. doi:10.1039/c5ra03653d.
8. ^ 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. PMID 342691.