Ibuprofen (布洛芬 )
Monoisotopic: 206.130679820
Ibuprofen, a propionic acid derivative, is a prototypical nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties.
- Abbott laboratories pharmaceutical products div
- Actavis mid atlantic llc
- Advent pharmaceuticals inc
- Alra laboratories inc
- Alterna tchp llc
- Amneal pharmaceuticals ny llc
- Banner pharmacaps inc
- Basf corp
- Bayer healthcare llc
- Bristol myers products inc
- Contract pharmacal corp
- Cumberland pharmaceuticals inc
- Dr reddys laboratories inc
- Dr reddys laboratories louisiana llc
- Dr reddys laboratories ltd
- Halsey drug co inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- L perrigo co
- Lederle laboratories div american cyanamid co
- Leiner health products inc
- Lnk international inc
- Lundbeck inc
- Marksans pharma ltd
- Mcneil consumer healthcare
- Mcneil consumer healthcare div mcneil ppc inc
- Mcneil consumer products co div mcneilab inc
- Mcneil pediatrics
- Mutual pharmaceutical co inc
- Mylan laboratories inc
- Mylan pharmaceuticals inc
- Northstar healthcare holdings ltd
- Ohm corp
- Ohm laboratories inc
- Par pharmaceutical inc
- Perrigo co
- Perrigo r and d co
- Pliva inc
- Purepac pharmaceutical co
- Sandoz inc
- Shasun usa inc
- Superpharm corp
- Teva pharmaceuticals usa inc
- Tris pharma inc
- Vintage pharmaceuticals inc
- Watson laboratories inc
- Wyeth consumer healthcare
Synthesis Reference | Not Available |
General Reference |
|
Form | Route | Strength |
---|---|---|
Capsule | Oral | 200 mg |
Concentrate | Intravenous | 100 mg/ml |
Suspension | Oral | 100 mg/5 ml |
Suspension | Oral | 40 mg/ml |
Tablet | Oral | 200 mg |
Tablet | Oral | 400 mg |
Tablet | Oral | 600 mg |
Tablet | Oral | 800 mg |
Tablet, chewable | Oral | 100 mg |
Tablet, chewable | Oral | 50 mg |
Tablet, film coated | Oral | 100 mg |
Tablet, film coated | Oral | 200 mg |
Tablet, film coated | Oral | 400 mg |
Tablet, film coated | Oral | 600 mg |
Tablet, film coated | Oral | 800 mg |
Unit description | Cost | Unit |
---|---|---|
Neoprofen 20 mg/2 ml vial | 304.5 USD | ml |
Caldolor 400 mg/4 ml vial | 2.21 USD | ml |
Caldolor 800 mg/8 ml vial | 1.58 USD | ml |
Nuprin arthritis patch | 1.11 USD | patch |
Ibuprofen powder | 1.04 USD | g |
Nuprin muscle & joint patch | 1.03 USD | patch |
Profen II 45-800 mg 12 Hour tablet | 0.69 USD | tablet |
Motrin 800 mg tablet | 0.59 USD | tablet |
Advil allergy sinus caplet | 0.5 USD | caplet |
Ibu-drops 40 mg/ml suspension drops | 0.42 USD | ml |
Motrin 600 mg tablet | 0.4 USD | tablet |
Ibuprofen 800 mg tablet | 0.36 USD | tablet |
Ibuprofen 400 mg tablet | 0.35 USD | tablet |
Infant's motrin 50 mg/1.25 ml | 0.34 USD | ml |
Childs ibuprofen susp drp | 0.33 USD | ml |
Ibuprofen 600 mg tablet | 0.33 USD | tablet |
Wal-profen cold & sinus cplt | 0.3 USD | caplet |
Infant ibuprofen susp drop | 0.29 USD | ml |
Motrin 400 mg tablet | 0.29 USD | tablet |
CVS Pharmacy infant ibuprofen susp drop | 0.25 USD | ml |
Infants medi-profen susp | 0.23 USD | ml |
Advil cold & sinus caplet | 0.22 USD | caplet |
Advil pm caplet | 0.22 USD | caplet |
Soba profen cold-sinus tablet | 0.22 USD | tablet |
Midol caplet | 0.21 USD | caplet |
Advil migraine 200 mg capsule | 0.2 USD | capsule |
Ibuprofen cold-sinus caplet | 0.2 USD | caplet |
Motrin 100 mg caplet | 0.2 USD | caplet |
Motrin pm caplet | 0.2 USD | caplet |
Advil 200 mg liqui-gel capsule | 0.19 USD | capsule |
Soba profen ib caplet | 0.19 USD | caplet |
Motrin 100 mg tablet chew | 0.18 USD | tablet |
Pub infants profenib drops | 0.18 USD | ml |
Sm ibuprofen ib 100 mg tablet | 0.18 USD | tablet |
Eck ibuprofen jr caplet | 0.17 USD | caplet |
Ibuprofen pm caplet | 0.17 USD | caplet |
Advil 200 mg caplet | 0.15 USD | capsule |
Advil 200 mg gel caplet | 0.15 USD | caplet |
Advil 200 mg tablet | 0.15 USD | tablet |
Ibuprofen 100 mg tablet chew | 0.15 USD | tablet |
Motrin ib 200 mg caplet | 0.15 USD | caplet |
Apo-Ibuprofen 600 mg Tablet | 0.14 USD | tablet |
CVS Pharmacy ibuprofen jr str 100 mg tablet | 0.14 USD | tablet |
Nu-Ibuprofen 600 mg Tablet | 0.14 USD | tablet |
Motrin ib 200 mg tablet | 0.13 USD | tablet |
Motrin ib 200 mg gelcap | 0.12 USD | capsule |
Nuprin 200 mg caplet | 0.12 USD | caplet |
Wal-profen 200 mg caplet | 0.12 USD | caplet |
Wal-profen 200 mg tablet | 0.12 USD | tablet |
Eql ibuprofen 200 mg tablet | 0.1 USD | tablet |
Nuprin 200 mg tablet | 0.1 USD | tablet |
Apo-Ibuprofen 400 mg Tablet | 0.08 USD | tablet |
Ibuprofen ib 200 mg tablet | 0.08 USD | tablet |
Novo-Profen 400 mg Tablet | 0.08 USD | tablet |
Apo-Ibuprofen 300 mg Tablet | 0.07 USD | tablet |
Medi-profen 200 mg tablet | 0.07 USD | tablet |
Ibuprofen 100 mg/5ml Suspension | 0.06 USD | ml |
Ibuprofen 200 mg caplet | 0.06 USD | caplet |
Child ibuprofen susp | 0.05 USD | ml |
Children's medi-profen susp | 0.05 USD | ml |
Children's motrin cold suspension | 0.05 USD | ml |
CVS Pharmacy ibuprofen 200 mg tablet | 0.05 USD | tablet |
Ibuprofen cold suspension | 0.05 USD | ml |
I-prin 200 mg tablet | 0.05 USD | tablet |
Novo-Profen 600 mg Tablet | 0.05 USD | tablet |
Children's motrin cold | 0.04 USD | ml |
Pv ibuprofen 200 mg caplet | 0.04 USD | caplet |
Soba children's profenib susp | 0.04 USD | ml |
Ibuprofen 200 mg tablet | 0.03 USD | tablet |
CVS Pharmacy ibuprofen 200 mg caplet | 0.02 USD | caplet |
Pv ibuprofen 200 mg tablet | 0.02 USD | tablet |
Type | small molecule |
Classes |
|
Substructures |
|
Indication | For symptomatic treatment of rheumatoid arthritis, juvenile rheumatoid arthritis and osteoarthritis. May be used to treat mild to moderate pain and for the management of dysmenorrhea. May be used to reduce fever. Has been used with some success for treating ankylosing spondylitis, gout and psoriatic arthritis. May reduce pain, fever and inflammation of pericarditis. May be used IV with opiates to relieve moderate to severe pain. Ibuprofen lysine may be used IV to treat patent ductus arteriosus (PDA) in premature neonates. | ||||||||||||||||||||||||||||||||||||||||||||||||||
Pharmacodynamics | Ibuprofen is a nonsteroidal anti-inflammatory agent (NSAIA) or nonsteroidal anti-inflammatory drug (NSAID), with analgesic and antipyretic properties. Ibuprofen has pharmacologic actions similar to those of other prototypical NSAIAs, which are thought to act through inhibition of prostaglandin synthesis. | ||||||||||||||||||||||||||||||||||||||||||||||||||
Mechanism of action | The exact mechanism of action of ibuprofen is unknown. Ibuprofen is a non-selective inhibitor of cyclooxygenase, an enzyme invovled in prostaglandin synthesis via the arachidonic acid pathway. Its pharmacological effects are believed to be due to inhibition cylooxygenase-2 (COX-2) which decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever and swelling. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Inhibition of COX-1 is thought to cause some of the side effects of ibuprofen including GI ulceration. Ibuprofen is administered as a racemic mixture. The R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo. The S-enantiomer is believed to be the more pharmacologically active enantiomer. | ||||||||||||||||||||||||||||||||||||||||||||||||||
Absorption | ~ 80% absorbed from GI tract
Time to reach peak plasma concentration = 47 minutes (suspension), 62 minutes (chewable tablets), 120 minutes (conventional tablets) |
||||||||||||||||||||||||||||||||||||||||||||||||||
Volume of distribution | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
Protein binding | 90-99% to whole human plasma and site II of purified albumin, binding appears to be saturable and becomes non-linear at concentrations exceeding 20 mcg/ml. | ||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolism |
R-enanatiomer undergoes extensive enantiomeric conversion (53-65%) to the more active S-enantiomer in vivo. Metablized by oxidation to 2 inactive metabolites: (+)-2[4´-(2-hydroxy-2-methylpropyl)phenyl]propionic acid and (+)-2-[4´-(2-carboxypropyl)phenyl]propionic acid. Very small amounts of 1-hydroxyibuprofen and 3-hydroxyibuprofen have been recovered from urine. Cytochrome P450 2C9 is the major catalyst in the formation of oxidative metabolites. Oxidative metabolites may be conjugated to glucuronide prior to excretion.
|
||||||||||||||||||||||||||||||||||||||||||||||||||
Route of elimination | Ibuprofen is rapidly metabolized and eliminated in the urine. | ||||||||||||||||||||||||||||||||||||||||||||||||||
Half life | 2-4 hours | ||||||||||||||||||||||||||||||||||||||||||||||||||
Clearance | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||
Toxicity | Side effects: May cause peripheral edema and fluid retention. Use caution in patients with congestive heart failure or severe uncontrolled hypertension. May cause dyspepsia, heartburn, nausea, vomiting, anorexia, diarrhea, constipation, stomatitis, flatulence, bloating, epigastric pain, and abdominal pain. Peptic ulcer and GI bleeding have been reported. May also cause dizziness, headache and nervousness. Acute renal failure accompanied by acute tubular necrosis has been reported. Most common symptoms of overdose are abdominal pain, nausea, vomiting, lethargy, vertigo, drowsiness (somnolence), dizziness and insomnia. Other symptoms of overdose include headache, loss of consciousness, tinnitus, CNS depression, convulsions and seizures. May rarely cause metabolic acidosis, abnormal hepatic function, hyperkalemia, renal failure, dyspnea, respiratory depression, coma, acute renal failure, and apnea (primarily in very young pediatric patients). LD50=1255mg/kg(orally in mice) |
||||||||||||||||||||||||||||||||||||||||||||||||||
Affected organisms |
|
||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways |
|
Properties | |||||||||||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
State | solid | ||||||||||||||||||||||||||||||||||||
Melting point | 75 - 77 oC | ||||||||||||||||||||||||||||||||||||
Experimental Properties |
|
||||||||||||||||||||||||||||||||||||
Predicted Properties |
|
Drug | Interaction |
---|---|
Acebutolol | Risk of inhibition of renal prostaglandins |
Acenocoumarol | The NSAID, ibuprofen, 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. |
Alendronate | Increased risk of gastric toxicity |
Anisindione | The NSAID, ibuprofen, may increase the anticoagulant effect of anisindione. |
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 |
Bumetanide | The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, bumetanide. |
Carteolol | Risk of inhibition of renal prostaglandins |
Carvedilol | Risk of inhibition of renal prostaglandins |
Cyclosporine | Monitor for nephrotoxicity |
Dicumarol | The NSAID, ibuprofen, may increase the anticoagulant effect of dicumarol. |
Esmolol | Risk of inhibition of renal prostaglandins |
Ethacrynic acid | The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, ethacrynic acid. |
Furosemide | The NSAID, ibuprofen, may antagonize the diuretic and antihypertensive effects of the loop diuretic, furosemide. |
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, ibuprofen, may decrease the renal excretion of lithium. Increased risk of lithium toxicity. |
Methotrexate | The NSAID, ibuprofen, 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 |
Propranolol | Risk of inhibition of renal prostaglandins |
Sotalol | Risk of inhibition of renal prostaglandins |
Tamoxifen | Ibuprofen may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Ibuprofen is initiated, discontinued or dose changed. |
Tolbutamide | Ibuprofen, 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 Ibuprofen is initiated, discontinued or dose changed. |
Torasemide | The NSAID, ibuprofen, may decrease the diuretic and antihypertensive effect of the loop diuretic, torasemide. |
Trandolapril | The NSAID, Ibuprofen, may reduce the antihypertensive effect of Trandolapril. Consider alternate therapy or monitor for changes in Trandolapril efficacy if Ibuprofen is initiated, discontinued or dose changed. |
Treprostinil | The prostacyclin analogue, Treprostinil, may increase the risk of bleeding when combined with the NSAID, Ibuprofen. Monitor for increased bleeding during concomitant thearpy. |
Trimethoprim | The strong CYP2C9 inhibitor, Ibuprofen, 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 Ibuprofen is initiated, discontinued or dose changed. |
Voriconazole | Ibuprofen, 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 ibuprofen is initiated, discontinued or dose changed. |
Warfarin | Ibuprofen, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. The antiplatelet effect of ibuprofen 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 ibuprofen is initiated, discontinued or dose changed. |
- Avoid alcohol.
- Food delays the time to reach peak plasma concentrations by 30-60 minutes and reduces peak plasma concentrations by 30-50%. Extent of absorption is unaffected.
- Take with food to reduce gastric irritation.