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Showing drug card for Piroxicam (DB00554)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:47:47
Primary Accession Number DB00554
Secondary Accession Number
  • APRD01187
Name Piroxicam
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily. [PubChem]
Synonyms
  1. AK1015
  2. piroxicam
Brand Names
  1. Akten
  2. Apo-Piroxicam
  3. Artroxicam
  4. Baxo
  5. Bruxicam
  6. Caliment
  7. Erazon
  8. Feldene
  9. Flogobene
  10. Geldene
  11. Improntal
  12. Larapam
  13. Pipoxicam
  14. Pirkam
  15. Piroflex
  16. Reudene
  17. Riacen
  18. Roxicam
  19. Roxiden
  20. Sasulen
  21. Solocalm
  22. Zunden
  23. piroxicam usp
Brand Mixtures Not Available
Chemical IUPAC Name (3E)-3-[hydroxy-(pyridin-2-ylamino)methylidene]-2-methyl-1,1-dioxobenzo[e]thiazin-4-one
Chemical Formula C15H13N3O4S
Chemical Structure Structure
CAS Registry Number 36322-90-4
InChI Identifier InChI=1/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/h2-9,20H,1H3,(H,16,17)/b15-13+/f/h17H
InChI Key LDJVNWFKNMYYNT-MXKJDJCZDU
KEGG Drug D00127 Link Image
KEGG Compound C01608 Link Image
PubChem Compound 5280452 Link Image
PubChem Substance 4761 Link Image
ChEBI ID Not Available
PharmGKB ID PA450985 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00658839 Link Image
RxList Link http://www.rxlist.com/cgi/generic/piroxicam.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/fel1173.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Piroxicam Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 331.3460
Monoisotopic Molecular Weight 331.0627
State Solid
Melting Point 198-200 oC
Experimental Water Solubility 23 mg/L Source: PhysProp
Predicted Water Solubility 6.05e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3 Source: PhysProp
Predicted LogP 1.81 Calculated using ALOGPS
Experimental LogS -4.16 [ADME Research, USCD]
Predicted LogS -3.74 Calculated using ALOGPS
Experimental Caco2 Permeability -4.45 [ADME Research, USCD]
pKa/Isoelectric Point 6.3
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN1S(=O)(=O)C2=CC=CC=C2C(=O)\C1=C(/O)NC1=CC=CC=N1
Canonical SMILES CN1S(=O)(=O)C2=CC=CC=C2C(=O)C1=C(O)NC1=CC=CC=N1
Drug Category
  • Anti-Inflammatory Agents, Non-Steroidal
  • Cyclooxygenase Inhibitors
ATC Codes
AHFS Codes
  • 28:08.04.92
Indication For treatment of osteoarthritis and rheumatoid arthritis.
Pharmacology Piroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). Piroxicam works by reducing hormones that cause inflammation and pain in the body. Piroxicam is used to reduce the pain, inflammation, and stiffness caused by rheumatoid arthritis and osteoarthritis.
Mechanism of Action The antiinflammatory effect of Piroxicam may result from the reversible inhibition of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. The prostaglandins are produced by an enzyme called Cox-1. Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets.
Absorption Well absorbed following oral administration.
Toxicity Symptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.
Protein Binding Not Available
Biotransformation Renal
Half Life 30 to 86 hours
Dosage Forms
Form Route
Capsule Oral
Suppository Rectal
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acebutolol Risk of inhibition of renal prostaglandins
Acenocoumarol The NSAID increases the anticoagulant effect
Alendronate Increased risk of gastric toxicity
Anisindione The NSAID increases the anticoagulant effect
Atenolol Risk of inhibition of renal prostaglandins
Betaxolol Risk of inhibition of renal prostaglandins
Bevantolol Risk of inhibition of renal prostaglandins
Bisoprolol Risk of inhibition of renal prostaglandins
Carteolol Risk of inhibition of renal prostaglandins
Carvedilol Risk of inhibition of renal prostaglandins
Cyclosporine Monitor for nephrotoxicity
Dicumarol The NSAID increases the anticoagulant effect
Esmolol Risk of inhibition of renal prostaglandins
Labetalol Risk of inhibition of renal prostaglandins
Lithium The NSAID increases serum levels of lithium
Methotrexate The NSAID increases the effect and toxicity of methotrexate
Metoprolol Risk of inhibition of renal prostaglandins
Nadolol Risk of inhibition of renal prostaglandins
Oxprenolol Risk of inhibition of renal prostaglandins
Penbutolol Risk of inhibition of renal prostaglandins
Pindolol Risk of inhibition of renal prostaglandins
Practolol Risk of inhibition of renal prostaglandins
Propranolol Risk of inhibition of renal prostaglandins
Ritonavir Ritonavir increases the toxicity of piroxicam
Sotalol Risk of inhibition of renal prostaglandins
Timolol Risk of inhibition of renal prostaglandins
Warfarin The NSAID increases the anticoagulant effect
Food Interactions
  • Take with food. Avoid alcohol.
Pathways
Name SMPDB Link KEGG Link
Piroxicam Pathway SMP00077 Link Image
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
  4. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Prostaglandin G/H synthase 1
Drug Target 1 [top]
Target 1 ID 20
Target 1 Name Prostaglandin G/H synthase 1
Target 1 Synonyms
  1. COX-1
  2. Cyclooxygenase- 1
  3. EC 1.14.99.1
  4. PGH synthase 1
  5. PGHS-1
  6. PHS 1
  7. Prostaglandin G/H synthase 1 precursor
  8. Prostaglandin H2 synthase 1
  9. Prostaglandin-endoperoxide synthase 1
Target 1 Gene Name PTGS1
Target 1 Protein Sequence >Prostaglandin G/H synthase 1 precursor 
MSRSLLLRFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFGLDRYQCDCTR
TGYSGPNCTIPGLWTWLRNSLRPSPSFTHFLLTHGRWFWEFVNATFIREMLMRLVLTVRS
NLIPSPPTYNSAHDYISWESFSNVSYYTRILPSVPKDCPTPMGTKGKKQLPDAQLLARRF
LLRRKFIPDPQGTNLMFAFFAQHFTHQFFKTSGKMGPGFTKALGHGVDLGHIYGDNLERQ
YQLRLFKDGKLKYQVLDGEMYPPSVEEAPVLMHYPRGIPPQSQMAVGQEVFGLLPGLMLY
ATLWLREHNRVCDLLKAEHPTWGDEQLFQTTRLILIGETIKIVIEEYVQQLSGYFLQLKF
DPELLFGVQFQYRNRIAMEFNHLYHWHPLMPDSFKVGSQEYSYEQFLFNTSMLVDYGVEA
LVDAFSRQIAGRIGGGRNMDHHILHVAVDVIRESREMRLQPFNEYRKRFGMKPYTSFQEL
VGEKEMAAELEELYGDIDALEFYPGLLLEKCHPNSIFGESMIEIGAPFSLKGLLGNPICS
PEYWKPSTFGGEVGFNIVKTATLKKLVCLNTKTCPYVSFRVPDASQDDGPAVERPSTEL
Target 1 Number of Residues 608
Target 1 Molecular Weight 68657
Target 1 Theoretical pI 7.39
Target 1 GO Classification
Function
antioxidant activity
peroxidase activity
Process
Not Available
Component
Not Available
Target 1 General Function Involved in peroxidase activity
Target 1 Specific Function May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells
Target 1 Pathways
Name SMPDB Link KEGG Link
Prostaglandin and leukotriene metabolism map00590 Link Image
Target 1 Reactions
  • arachidonate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-23
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 387018 Link Image
Target 1 UniProtKB/Swiss-Prot ID P23219 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PGH1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Microsome
  • microsomal membrane
  • peripheral membrane protein
Target 1 Gene Sequence >1800 bp 
ATGAGCCGGAGTCTCTTGCTCCGGTTCTTGCTGTTGCTGCTCCTGCTCCCGCCGCTCCCC
GTCCTGCTCGCGGACCCAGGGGCGCCCACGCCAGTGAATCCCTGTTGTTACTATCCATGC
CAGCACCAGGGCATCTGTGTCCGCTTCGGCCTTGACCGCTACCAGTGTGACTGCACCCGC
ACGGGCTATTCCGGCCCCAACTGCACCATCCCTGGCCTGTGGACCTGGCTCCGGAATTCA
CTGCGGCCCAGCCCCTCTTTCACCCACTTCCTGCTCACTCACGGGCGCTGGTTCTGGGAG
TTTGTCAATGCCACCTTCATCCGAGAGATGCTCATGCTCCTGGTACTCACAGTGCGCTCC
AACCTTATCCCCAGTCCCCCCACCTACAACTCTGCACATGACTACATCAGCTGGGAGTCT
TTCTCCAACGTGAGCTATTACACTCGTATTCTGCCCTCTGTGCCTAAAGATTGCCCCACA
CCCATGGGAACCAAAGGGAAGAAGCAGTTGCCAGATGCCCAGCTCCTGGCCCGCCGCTTC
CTGCTCAGGAGGAAGTTCATACCTGACCCCCAAGGCACCAACCTCATGTTTGCCTTCTTT
GCACAACACTTCACCCACCAGTTCTTCAAAACTTCTGGCAAGATGGGTCCTGGCTTCACC
AAGGCCTTGGGCCATGGGGTAGACCTCGGCCACATTTATGGAGACAATCTGGAGCGTCAG
TATCAACTGCGGCTCTTTAAGGATGGGAAACTCAAGTACCAGGTGCTGGATGGAGAAATG
TACCCGCCCTCGGTAGAAGAGGCGCCTGTGTTGATGCACTACCCCCGAGGCATCCCGCCC
CAGAGCCAGATGGCTGTGGGCCAGGAGGTGTTTGGGCTGCTTCCTGGGCTCATGCTGTAT
GCCACGCTCTGGCTACGTGAGCACAACCGTGTGTGTGACCTGCTGAAGGCTGAGCACCCC
ACCTGGGGCGATGAGCAGCTTTTCCAGACGACCCGCCTCATCCTCATAGGGGAGACCATC
AAGATTGTCATCGAGGAGTACGTGCAGCAGCTGAGTGGCTATTTCCTGCAGCTGAAATTT
GACCCAGAGCTGCTGTTCGGTGTCCAGTTCCAATACCGCAACCGCATTGCCACGGAGTTC
AACCATCTCTACCACTGGCACCCCCTCATGCCTGACTCCTTCAAGGTGGGCTCCCAGGAG
TACAGCTACGAGCAGTTCTTGTTCAACACCTCCATGTTGGTGGACTATGGGGTTGAGGCC
CTGGTGGATGCCTTCTCTCGCCAGATTGCTGGCCGGATCGGTGGGGGCAGGAACATGGAC
CACCACATCCTGCATGTGGCTGTGGATGTCATCAGGGAGTCTCGGGAGATGCGGCTGCAG
CCCTTCAATGAGTACCGCAAGAGGTTTGGCATGAAACCCTACACCTCCTTCCAGGAGCTC
GTAGGAGAGAAGGAGATGGCAGCAGAGTTGGAGGAATTGTATGGAGACATTGATGCGTTG
GAGTTCTACCCTGGACTGCTTCTTGAAAAGTGCCATCCAAACTCTATCTTTGGGGAGAGT
ATGATAGAGATTGGGGCTCCCTTTTCCCTCAAGGGTCTCCTAGGGAATCCCATCTGTTCT
CCGGAGTACTGGAAGCCGAGCACATTTGGCGGCGAGGTGGGCTTTAACATTGTCAAGACG
GCCACACTGAAGAAGCTGGTCTGCCTCAACACCAAGACCTGTCCCTACGTTTCCTTCCGT
GTGCCGGATGCCAGTCAGGATGATGGGCCTGCTGTGGAGCGACCATCCACAGAGCTCTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID PTGS1 Link Image
Target 1 GenAtlas ID PTGS1 Link Image
Target 1 HGNC ID HGNC:9604 Link Image
Target 1 Chromosome Location 9
Target 1 Locus 9q32-q33.3
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Diaz A, Reginato AM, Jimenez SA: Alternative splicing of human prostaglandin G/H synthase mRNA and evidence of differential regulation of the resulting transcripts by transforming growth factor beta 1, interleukin 1 beta, and tumor necrosis factor alpha. J Biol Chem. 1992 May 25;267(15):10816-22. [PubMed Link Image]
  2. Takahashi Y, Ueda N, Yoshimoto T, Yamamoto S, Yokoyama C, Miyata A, Tanabe T, Fuse I, Hattori A, Shibata A: Immunoaffinity purification and cDNA cloning of human platelet prostaglandin endoperoxide synthase (cyclooxygenase). Biochem Biophys Res Commun. 1992 Jan 31;182(2):433-8. [PubMed Link Image]
  3. Funk CD, Funk LB, Kennedy ME, Pong AS, Fitzgerald GA: Human platelet/erythroleukemia cell prostaglandin G/H synthase: cDNA cloning, expression, and gene chromosomal assignment. FASEB J. 1991 Jun;5(9):2304-12. [PubMed Link Image]
  4. Yokoyama C, Tanabe T: Cloning of human gene encoding prostaglandin endoperoxide synthase and primary structure of the enzyme. Biochem Biophys Res Commun. 1989 Dec 15;165(2):888-94. [PubMed Link Image]
Target 1 Drug References
  1. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed Link Image]
  2. Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [PubMed Link Image]
  3. Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [PubMed Link Image]
  4. Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [PubMed Link Image]
  5. Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.