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药品详细

Ketoprofen (酮基布洛芬 )

化学结构式图
中文名
酮基布洛芬
英文名
Ketoprofen
分子式
Not Available
化学名
2-(3-benzoylphenyl)propanoic acid
分子量
Average: 254.2806
Monoisotopic: 254.094294314
CAS号
22071-15-4
ATC分类
M01A 未知;M01A 未知;M02A 未知
药物类型
small molecule
阶段
商品名
Actron;Alrheumat;Alrheumun;Capisten;Dexal;Epatec;Fastum;Iso-K;Kefenid;Ketopron;Lertus;Menamin;Meprofen;Orudis;Orudis KT;Orugesic;Oruvail (Wyeth);Oscorel;Profenid;Toprec;Toprek;
同义名
m-Benzoylhydratropic acid;
基本介绍

Ketoprofen, a propionic acid derivative, is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.

生产厂家
  • Bayer healthcare llc
  • Elan pharmaceutical research corp
  • Heritage pharmaceuticals inc
  • L perrigo co
  • Mylan pharmaceuticals inc
  • Novartis consumer health inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc florida
  • Wyeth ayerst laboratories
  • Wyeth consumer healthcare
  • Wyeth pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. Pubmed
剂型
Form Route Strength
Capsule Oral 100 mg
Capsule Oral 50 mg
Capsule Oral 75 mg
Capsule, extended release Oral 200 mg
规格
Unit description Cost Unit
Ketoprofen powder 43.74 USD g
Ketoprofen micronized powder 3.84 USD g
Ketoprofen CR 200 mg 24 Hour Capsule 2.8 USD capsule
Orudis 75 mg capsule 1.58 USD capsule
Apo-Keto Sr 200 mg Sustained-Release Tablet 1.46 USD tablet
Ketoprofen 75 mg capsule 1.12 USD capsule
Pms-Ketoprofen 100 mg Suppository 1.1 USD suppository
Ketoprofen 50 mg capsule 1.0 USD capsule
Apo-Keto-E 100 mg Enteric-Coated Tablet 0.71 USD tablet
Apo-Keto 50 mg Capsule 0.35 USD capsule
Apo-Keto-E 50 mg Enteric-Coated Tablet 0.35 USD tablet
Orudis kt 12.5 mg tablet 0.3 USD tablet
化合物类型
Type small molecule
Classes
  • Benzophenones
Substructures
  • Hydroxy Compounds
  • Acetates
  • Carboxylic Acids and Derivatives
  • Phenylacetates
  • Benzene and Derivatives
  • Aromatic compounds
  • Benzophenones
  • Benzoyl Derivatives
  • Ketones
适应症
ANTIINFLAMMATORY AND ANTIRHEUMATIC 消炎抗风湿;
药理
Indication For symptomatic treatment of acute and chronic rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, primary dysmenorrhea and mild to moderate pain associated with musculotendinous trauma (sprains and strains), postoperative (including dental surgery) or postpartum pain.
Pharmacodynamics Ketoprofen is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties. Ketoprofen has pharmacologic actions similar to those of other prototypical NSAIDs, which inhibit prostaglandin synthesis. Ketoprofen is used to treat rheumatoid arthritis, osteoarthritis, dysmenorrhea, and alleviate moderate pain.
Mechanism of action The anti-inflammatory effects of ketoprofen are believed to be due to inhibition cylooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis via the arachidonic acid pathway. This results in decreased levels of prostaglandins that mediate pain, fever and inflammation. Ketoprofen is a non-specific cyclooxygenase inhibitor and inhibition of COX-1 is thought to confer some of its side effects, such as GI upset and ulceration. Ketoprofen is thought to have anti-bradykinin activity, as well as lysosomal membrane-stabilizing action. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.
Absorption Ketoprofen is rapidly and well-absorbed orally, with peak plasma levels occurring within 0.5 to 2 hours.
Volume of distribution Not Available
Protein binding 99% bound, primarily to albumin
Metabolism

Rapidly and extensively metabolized in the liver, primarily via conjugation to glucuronic acid. No active metabolites have been identified.

Route of elimination In a 24 hour period, approximately 80% of an administered dose of ketoprofen is excreted in the urine, primarily as the glucuronide metabolite.
Half life Conventional capsules: 1.1-4 hours

Extended release capsules: 5.4 hours due to delayed absorption (intrinsic clearance is same as conventional capsules)
Clearance
  • Oral-dose cl=6.9 +/- 0.8 L/h [Ketoprofen Immediate-release capsules (4 × 50 mg)]
  • Oral-dose cl=6.8 +/- 1.8 L/h [Ketoprofen Extended-release capsules (1 × 200 mg)]
  • 0.08 L/kg/h
  • 0.7 L/kg/h [alcoholic cirrhosis patients]
Toxicity LD50=62.4 mg/kg (rat, oral).

Symptoms of overdose include drowsiness, vomiting and abdominal pain.

Side effects are usually mild and mainly involved the GI tract. Most common adverse GI effect is dyspepsia (11% of patients). May cause nausea, diarrhea, abdominal pain, constipation and flatulence in greater than 3% of patients.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00085 Ketoprofen Pathway SMP00085
理化性质
Properties
State solid
Melting point 94 oC
Experimental Properties
Property Value Source
water solubility 51 mg/L PhysProp
logP 3.2 PhysProp
logS -3.7 [ADME Research, USCD] PhysProp
pKa 4.45 Various sources
Predicted Properties
Property Value Source
water solubility 2.13e-02 g/l ALOGPS
logP 3.29 ALOGPS
logP 3.61 ChemAxon Molconvert
logS -4.08 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 54.37 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 72.52 ChemAxon Molconvert
polarizability 26.56 ChemAxon Molconvert
药物相互作用
Drug Interaction
Acenocoumarol The NSAID, ketoprofen, may increase the anticoagulant effect of acenocoumarol.
Acetylsalicylic acid Concomitant therapy of the NSAID, ketoprofen, and acetylsalicylic acid may result in additive adverse/toxic effects (e.g. GI bleeding). The NSAID may also limit the cardioprotective effect of acetylsalicylic acid. Occasional concomitant use may not cause clinically significant problems, but regular, frequent concomitant therapy is not recommended.
Anisindione The NSAID, ketoprofen, may increase the anticoagulant effect of anisindione.
Citalopram Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
Cyclosporine The NSAID, ketoprofen, may increase the serum concentration of cyclosporine. Ketoprofen may also increase the nephrotoxicity of cyclosporine.
Dicumarol The NSAID, ketoprofen, may increase the anticoagulant effect of dicumarol.
Drotrecogin alfa The antiplatelet effect of ketoprofen may increase the bleed risk associated with drotrecogin alfa. Consider spacing use of the two agents by at least 7 days. Increase monitoring for signs and symptoms of bleeding during concomitant therapy.
Escitalopram Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
Fluoxetine Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
Fluvoxamine Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
Ginkgo biloba Increased risk of bleeding due to additive antiplatelet properties of the two agents. Concomitant therapy should be avoided or monitored carefully for bleeding, bruising and altered mental status, which may be caused by CNS bleeds.
Ginseng Increased risk of bleeding due to additive anticoagulant properties of the two agents. Concomitant therapy should be avoided or monitored carefully for bleeding, bruising and altered mental status, which may be caused by CNS bleeds.
Ketorolac Concomitant use of ketoprofen and ketorolac, two NSAIDs, is contraindicated due to the risk of additive or synergistic NSAID toxicities (e.g. GI bleeding, ulceration, renal dysfunction, etc).
Lithium The NSAID, ketoprofen, may increase the serum concentration of lithium by decreasing its renal clearance. Consider a dose reduction in lithium upon initiation of ketoprofen therapy. Monitor for changes in the therapeutic and adverse effects of lithium if ketoprofen is initiated, discontinued or does changed.
Methotrexate The NSAID, ketoprofen, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
Paroxetine Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
Pemetrexed The NSAID, ketoprofen, may increase increase the serum concentration of pemetrexed by decreasing its renal clearance. Patients with mild to moderate renal insufficiency (CrCl 45-79 ml/min) should avoid use of ketoprofen within 2 days of a pemetrexed dose. Patients with better renal function do not appear to be at risk. Monitor for toxicity in all patients during concomitant therapy.
S-Adenosylmethionine Increased risk of bleeding due to additive antiplatelet properties of the two agents. Concomitant therapy should be avoided or monitored carefully for bleeding, bruising and altered mental status, which may be caused by CNS bleeds.
Sertraline Concomitant therapy may result in additive antiplatelet effects and increase the risk of bleeding. Monitor for increased risk of bleeding during concomitant therapy.
Telmisartan Concomitant use of Telmisartan and Ketoprofen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Timolol The NSAID, Ketoprofen, may antagonize the antihypertensive effect of Timolol.
Trandolapril The NSAID, Ketoprofen, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Ketoprofen is initiated, discontinued or dose changed.
Treprostinil The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Ketoprofen. Monitor for increased bleeding during concomitant thearpy.
Warfarin The antiplatelet effects of ketoprofen 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
  • Avoid alcohol.
  • Food prolongs rate of absorption and decreases peak plasma concentration. Extent of absorption is not affected.
  • Take with food to reduce gastric irritation.

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