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药品详细

Oxaprozin(奥沙普秦)

化学结构式图
中文名
奥沙普秦
英文名
Oxaprozin
分子式
C18H15NO3
化学名
3-(diphenyl-1,3-oxazol-2-yl)propanoic acid
分子量
Average: 293.3166
Monoisotopic: 293.105193351
CAS号
21256-18-8
ATC分类
M01A 未知
药物类型
small molecule
阶段
approved
商品名
Alvo;Daypro;Daypro Alta;Deflam;Voir;
同义名
Oxaprozina [INN-Spanish];Oxaprozine [INN-French];Oxaprozinum [INN-Latin];
基本介绍

Oxaprozin is a non-narcotic, non-steroidal anti-inflammatory drug (NSAID), used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis.

生产厂家
  • Actavis elizabeth llc
  • Apotex inc etobicoke site
  • Caraco pharmaceutical laboratories ltd
  • Dr reddys laboratories ltd
  • Gd searle llc
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories
封装厂家
参考
Synthesis Reference
  1. Zhou XP, Zhang MX, Sun W, Yang XH, Wang GS, Sui DY, Yu XF, Qu SC: Design, synthesis, and in-vivo evaluation of 4,5-diaryloxazole as novel nonsteroidal anti-inflammatory drug. Biol Pharm Bull. 2009 Dec;32(12):1986-90. Pubmed
General Reference
  1. Heller B, Tarricone R: Oxaprozin versus diclofenac in NSAID-refractory periarthritis pain of the shoulder. Curr Med Res Opin. 2004 Aug;20(8):1279-90. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Phenylpropenes
Substructures
  • Hydroxy Compounds
  • Acetates
  • Phenylpropenes
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Oxazoles
  • Imines
适应症
ANTIINFLAMMATORY AND ANTIRHEUMATIC 消炎抗风湿;
药理
Indication Used to relieve the inflammation, swelling, stiffness, and joint pain associated with rheumatoid arthritis and osteoarthritis.
Pharmacodynamics Oxaprozin is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Oxaprozin is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and to alleviate moderate pain.
Mechanism of action Anti-inflammatory effects of Oxaprozin are believed to be due to inhibition of cylooxygenase in platelets which leads to the blockage of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Oxaprozin is a non-selective NSAID, with a cell assay system showing lower COX-2 selectivity implying higher COX-1 selectivity.
Absorption Oxaprozin is 95% absorbed after oral administration. Food may reduce the rate of absorption of oxaprozin, but the extent of absorption is unchanged. Antacids do not significantly affect the extent and rate of oxaprozin absorption.
Volume of distribution
  • 11 to 17 L/70 kg
Protein binding >99.5% bound to albumin
Metabolism
Hepatic. Ester and ether glucuronide are the major conjugated metabolites of oxaprozin, and do not have significant pharmacologic activity.
Route of elimination Oxaprozin is expected to be excreted in human milk based on its physical-chemical properties; however, the amount of oxaprozin excreted in breast milk has not been evaluated. Approximately 95% of oxaprozin is metabolized by the liver. Approximately 5% of the oxaprozin dose is excreted unchanged in the urine. Sixty-five percent (65%) of the dose is excreted in the urine and 35% in the feces as metabolite. Biliary excretion of unchanged oxaprozin is a minor pathway. Several oxaprozin metabolites have been identified in human urine or feces.
Half life 54.9 hours
Clearance Not Available
Toxicity Oral, mouse: LD50 = 1210 mg/kg; Oral, rabbit: LD50 = 172 mg/kg; Oral, rat: LD50 = 4470 mg/kg
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00113 Oxaprozin Pathway SMP00113
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 158-159 °C Not Available
water solubility Insoluble Not Available
logP 4.19 HANSCH,C ET AL. (1995)
pKa 4.3 Not Available
Predicted Properties
Property Value Source
water solubility 3.25e-02 g/l ALOGPS
logP 3.33 ALOGPS
logP 3.46 ChemAxon
logS -4 ALOGPS
pKa (strongest acidic) 4.95 ChemAxon
pKa (strongest basic) -0.59 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 63.33 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 81.88 ChemAxon
polarizability 31.69 ChemAxon
药物相互作用
Drug Interaction
Acenocoumarol The NSAID, oxaprozin, may increase the anticoagulant effect of acenocoumarol.
Alendronate Increased risk of gastric toxicity
Anisindione The NSAID, oxaprozin, may increase the anticoagulant effect of anisinodione.
Azilsartan medoxomil Increases toxicity of each. May deteriorate renal function, particularly in volume depleted or elderly patients. Decreases effects of azilsartan by antagonism.
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, oxaprozin, may increase the anticoagulant effect of dicumarol.
Ginkgo biloba Additive anticoagulant/antiplatelet effects may increase bleed risk. Concomitant therapy should be avoided.
Methotrexate The NSAID, oxaprozin, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
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.
Telmisartan Concomitant use of Telmisartan and Oxaprozin may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Timolol The NSAID, Oxaprozin, may antagonize the antihypertensive effect of Timolol.
Trandolapril The NSAID, Oxaprozin, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Oxaprozin is initiated, discontinued or dose changed.
Treprostinil The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Oxaprozin. Monitor for increased bleeding during concomitant thearpy.
Warfarin The antiplatelet effects of oxaprozin may increase the bleed risk associated with warfarin. Consider alternate therapy or monitor for signs and symptoms of bleeding during concomitant therapy.
食物相互作用
  • Take with food, usually once a day after breakfast. Food decreases the rate of absorption but not the amount absorbed. Avoid alcohol.

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