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药品详细

Piroxicam(吡罗昔康)

化学结构式图
中文名
吡罗昔康
英文名
Piroxicam
分子式
C15H13N3O4S
化学名
4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1$l^{6},2-benzothiazine-3-carboxamide
分子量
Average: 331.346
Monoisotopic: 331.062676609
CAS号
36322-90-4
ATC分类
M01A 未知;M02A 未知;S01B 抗炎药
药物类型
small molecule
阶段
approved
商品名
Akten;Apo-Piroxicam;Artroxicam;Baxo;Bruxicam;Caliment;Erazon;Feldene;Flogobene;Geldene;Improntal;Larapam;Pipoxicam;Pirkam;Piroflex;piroxicam usp;Reudene;Riacen;Roxicam;Roxiden;Sasulen;Solocalm;Zunden;
同义名
AK1015;piroxicam;
基本介绍

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]

生产厂家
  • Akorn inc
  • Egis pharmaceuticals
  • Genpharm pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Nostrum laboratories inc
  • Pfizer laboratories div pfizer inc
  • Roxane laboratories inc
  • Scs pharmaceuticals
  • Teva pharmaceuticals usa
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference Not Available
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
ANTIINFLAMMATORY AND ANTIRHEUMATIC 消炎抗风湿;
药理
Indication For treatment of osteoarthritis and rheumatoid arthritis.
Pharmacodynamics 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.
Volume of distribution
  • 0.14 L/kg
Protein binding Not Available
Metabolism
Renal

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Piroxicam
5'-Hydroxypiroxicam Details
Route of elimination Piroxicam and its biotransformation products are excreted in urine and feces, with about twice as much appearing in the urine as in the feces. Approximately 5% of a piroxicam dose is excreted unchanged. However, a substantial portion of piroxicam elimination occurs by hepatic metabolism. Piroxicam is excreted into human milk.
Half life 30 to 86 hours
Clearance Not Available
Toxicity Symptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00077 Piroxicam Pathway SMP00077
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 198-200 °C PhysProp
water solubility 23 mg/L (at 22 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP 3.06 AVDEEF,A (1997)
logS -4.16 ADME Research, USCD
Caco2 permeability -4.45 ADME Research, USCD
pKa 6.3 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 1.43e-01 g/l ALOGPS
logP 2.2 ALOGPS
logP 0.6 ChemAxon
logS -3.4 ALOGPS
pKa (strongest acidic) 4.76 ChemAxon
pKa (strongest basic) 3.79 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 99.6 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 87.04 ChemAxon
polarizability 32.27 ChemAxon
药物相互作用
Drug Interaction
Acebutolol Risk of inhibition of renal prostaglandins
Acenocoumarol The NSAID, piroxicam, may increase the anticoagulant effect of acenocoumarol.
Alendronate Increased risk of gastric toxicity
Anisindione The NSAID, piroxicam, may increase the anticoagulant effect of anisindione.
Atenolol Risk of inhibition of renal prostaglandins
Azilsartan medoxomil Increases toxicity of each. May deteriorate renal function, particularly in volume depleted or elderly patients. Decreases effects of azilsartan by antagonism.
Betaxolol Nonsteroidal Anti-Inflammatory Agents such as piroxicam may diminish the antihypertensive effect of Beta-Blockers such as betaxolol. Monitor for increases in blood pressure if a nonsteroidal anti-inflammatory agent (NSAID) is initiated/dose increased, or decreases in blood pressure if a NSAID is discontinued/dose decreased; this is particularly important if NSAID treatment is for extended periods of time. Ophthalmic beta-blockers are likely of little concern.
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
Colesevelam Bile acid sequestrants may decrease the absorption of Nonsteroidal Anti-Inflammatory Agents. Monitor for decreased serum concentrations/therapeutic effects of nonsteroidal anti-inflammatory agents (NSAID) if coadministered with bile acid sequestrants. Separating the administration of doses by 2 or more hours may reduce (but not eliminate) the risk of interaction. The manufacturer of colesevelam recommends that drugs should be administered at least 1 hour before or 4 hours after colesevelam.
Cyclosporine Monitor for nephrotoxicity
Dicumarol The NSAID, piroxicam, may increase the anticoagulant effect of dicumarol.
Esmolol Risk of inhibition of renal prostaglandins
Ginkgo biloba Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Labetalol Risk of inhibition of renal prostaglandins
Lithium The NSAID, piroxicam, may decrease the renal excretion of lithium. Increased risk of lithium toxicity.
Methotrexate The NSAID, piroxicam, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
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
Pralatrexate NSAIDs increase the risk of toxicity due to impairment of renal clearance of pralatrexate thus increasing exposure. Monitor for adverse effects or adjust dose of pralatrexate.
Propranolol Risk of inhibition of renal prostaglandins
Ritonavir Ritonavir increases the toxicity of piroxicam
Sotalol Risk of inhibition of renal prostaglandins
Tamoxifen Piroxicam may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Piroxicam is initiated, discontinued or dose changed.
Telmisartan Concomitant use of Telmisartan and Piroxicam may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Timolol Risk of inhibition of renal prostaglandins
Tolbutamide Piroxicam, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Tolbutamide therapeutic and adverse effects if Piroxicam is initiated, discontinued or dose changed.
Torasemide Piroxicam, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Piroxicam is initiated, discontinued or dose changed.
Trandolapril The NSAID, Piroxicam, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Piroxicam is initiated, discontinued or dose changed.
Treprostinil The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Piroxicam. Monitor for increased bleeding during concomitant thearpy.
Triflusal The metabolite of triflusal, 2-hydroxy-4-trifluoro-methyl-benzoic acid (HTB), impairs the serum protein binding of glisentide to the same extent as acetylsalisylic acid. Thus, the free fraction of glisentide may be increased. A dosage reduction may be required if used in combination.
Trimethoprim The strong CYP2C9 inhibitor, Piroxicam, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Piroxicam is initiated, discontinued or dose changed.
Vilazodone Increased risk of bleeding with concomitant use of NSAIDs and vilazodone
Voriconazole Piroxicam, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if piroxicam is initiated, discontinued or dose changed.
Warfarin Piroxicam, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of piroxicam may also increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if piroxicam is initiated, discontinued or dose changed.
食物相互作用
  • Take with food. Avoid alcohol.

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