Identification

Name
Ibuprofen
Accession Number
DB01050  (APRD00372)
Type
Small Molecule
Groups
Approved
Description

Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) derived from propionic acid and it is considered the first of the propionics.[7] The formula of ibuprofen is 2-(4-isobutylphenyl) propionic acid and its initial development was in 1960 while researching for a safer alternative for aspirin.[8] Ibuprofen was finally patented in 1961 and this drug was first launched against rheumatoid arthritis in the UK in 1969 and USA in 1974. It was the first available over-the-counter NSAID.[9]

On the available products, ibuprofen is administered as a racemic mixture. Once administered, the R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo by the activity of the alpha-methylacyl-CoA racemase. The S-enantiomer is believed to be the more pharmacologically active enantiomer.[24]

Structure
Thumb
Synonyms
  • (±)-2-(p-isobutylphenyl)propionic acid
  • (±)-ibuprofen
  • (±)-p-isobutylhydratropic acid
  • (±)-α-methyl-4-(2-methylpropyl)benzeneacetic acid
  • (4-isobutylphenyl)-α-methylacetic acid
  • (RS)-ibuprofen
  • 2-(4-isobutylphenyl)propanoic acid
  • 4-isobutylhydratropic acid
  • Ibuprofene
  • Ibuprofeno
  • Ibuprofenum
  • Ibuprophen
  • α-(4-isobutylphenyl)propionic acid
  • α-(p-isobutylphenyl)propionic acid
Product Ingredients
IngredientUNIICASInChI Key
Ibuprofen aluminumD0YGZ1VO1B61054-06-6QAZIXAUMDFPQRW-UHFFFAOYSA-K
Ibuprofen lysineN01ORX9D6S57469-77-9IHHXIUAEPKVVII-ZSCHJXSPSA-N
Ibuprofen potassium48304089JJ79261-49-7XJELUCTZEAQYGF-UHFFFAOYSA-M
Ibuprofen sodiumRM1CE97Z4N527688-20-6VTGPMVCGAVZLQI-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Ibuprofen Tab 600mgTablet600 mgOralApotex Corporation1984-12-31Not applicableCanada
CaldolorInjection800 mg/8mLIntravenousCumberland Pharmaceuticals Inc.2009-06-11Not applicableUs
CaldolorSolution100 mgIntravenousAlveda Pharmaceuticals Inc2012-06-15Not applicableCanada
IbuprofenTablet, film coated400 mg/1OralDr Reddy's Laboratories2007-03-08Not applicableUs
IbuprofenTablet400 mg/1OralApace Packaging, Llc2013-01-10Not applicableUs
IbuprofenTablet, film coated800 mg/1OralDr Reddy's Laboratories2007-03-08Not applicableUs
IbuprofenTablet800 mg/1OralApace Packaging, Llc2013-01-10Not applicableUs
IbuprofenTablet, film coated600 mg/1OralDr Reddy's Laboratories2007-03-08Not applicableUs
IbuprofenTablet600 mg/1OralApace Packaging, Llc2013-01-10Not applicableUs
Ibuprofen-600 Tab 600mgTablet600 mgOralPro Doc Limitee1986-12-312014-07-24Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlivioTablet600 mg/600mgOralAlivio Medical Products, Llc2015-07-01Not applicableUs
AlivioTablet800 mg/800mgOralAlivio Medical Products, Llc2015-07-01Not applicableUs
AlivioTablet400 mg/400mgOralAlivio Medical Products, Llc2015-07-01Not applicableUs
Alti-ibuprofen Tab 600mgTablet600 mgOralAltimed Pharma Inc.1984-12-311999-09-17Canada
Comfort Pac with IbuprofenKit800 mg/1Pd Rx Pharmaceuticals, Inc.2012-09-06Not applicableUs
IbuTablet800 mg/1OralBlenheim Pharmacal, Inc.2012-03-23Not applicableUs
IbuTablet600 mg/1OralRed Pharm Drug, Inc.2008-11-20Not applicableUs
IbuTablet800 mg/1OralLake Erie Medical DBA Quality Care Products LLC2010-10-19Not applicableUs
IbuTablet600 mg/1OralNuCare Pharmaceuticals Inc.2008-11-20Not applicableUs
IbuTablet400 mg/1OralNucare Pharmaceuticals, Inc.2008-11-20Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
365 Everyday Value IbuprofenTablet, film coated200 mg/1OralWhole Foods Market, Inc.2018-08-29Not applicableUs
7 Select Childrens IbuprofenSuspension100 mg/5mLOral7 Eleven2014-08-05Not applicableUs
7 Select IbuprofenTablet, coated200 mg/1Oral7 Eleven2014-05-13Not applicableUs
7 Select IbuprofenCapsule, liquid filled200 mg/1Oral7 Eleven2018-02-02Not applicableUs
7 Select IbuprofenTablet, film coated200 mg/1Oral7 Eleven2014-08-07Not applicableUs
Actiprofen - Caplet 200mgTablet200 mgOralBayer Inc Consumer Care1996-12-311999-11-03Canada
AdvilTablet, coated200 mg/1OralWyeth Consumer Healthcare Llc1984-05-18Not applicableUs
AdvilTablet, coated256 mg/1OralWyeth Consumer Healthcare Llc2013-07-08Not applicableUs
AdvilTablet200 mg/1OralNavajo Manuracturing Company2016-09-20Not applicableUs
AdvilCapsule, liquid filled200 mg/1OralWyeth Consumer Healthcare Llc2017-03-08Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
10 Person ANSIIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Lidocaine (0.5 1/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B Sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitGenuine First Aid2010-04-24Not applicableUs
25 Person ANSIIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Isopropyl Alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B Sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitGenuine First Aid2010-04-25Not applicableUs
50 Person ANSIIbuprofen (200 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Ethanol (62 g/100g) + Isopropyl Alcohol (70 mL/100mL) + Lidocaine (0.5 g/100g) + Neomycin sulfate (5 mg/1g) + Polymyxin B Sulfate (5000 [iU]/1g) + Water (98.16 mL/100mL)KitGenuine First Aid2010-06-02Not applicableUs
7 Select Ibuprofen PMIbuprofen (200 mg/1) + Diphenhydramine citrate (38 mg/1)Tablet, film coatedOral7 Eleven2014-08-05Not applicableUs
7-Select Advil PMIbuprofen (200 mg/1) + Diphenhydramine citrate (38 mg/1)Tablet, coatedOralLil' Drug Store Products, Inc.2011-06-012017-12-31Us
Adventure Medical Kits 1-2 Person First AidIbuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Diphenhydramine hydrochloride (25 mg/1) + Ethanol (60 mL/100mL) + Neomycin sulfate (5 mg/1g) + Polymyxin B Sulfate (5000 [iU]/1g)KitTopicalTender Corp Dba Adventure Medical Kits2010-08-26Not applicableUs
Adventure Medical Kits 1-2 Person National Ski Patrol First AidIbuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Ethanol (60 mL/100mL) + Neomycin sulfate (5 mg/1g) + Polymyxin B Sulfate (5000 [iU]/1g)KitTender Corp Dba Adventure Medical Kits2010-08-26Not applicableUs
Adventure Medical Kits 1-4 Person First AidIbuprofen (200 mg/1) + Acetaminophen (500 mg/1) + Acetylsalicylic acid (325 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.40 mL/100mL) + Benzocaine (6 mL/100mL) + Diphenhydramine hydrochloride (25 mg/1) + Ethanol (60 mL/100mL) + Neomycin sulfate (5 mg/1g) + Polymyxin B Sulfate (5000 [iU]/1g)KitTopicalTender Corp Dba Adventure Medical Kits2010-08-26Not applicableUs
Advil Allergy and Congestion ReliefIbuprofen (200 mg/1) + Chlorpheniramine maleate (4 mg/1) + Phenylephrine hydrochloride (10 mg/1)Tablet, coatedOralPfizer2012-07-23Not applicableUs
Advil Allergy and Congestion ReliefIbuprofen (200 mg/1) + Chlorpheniramine maleate (4 mg/1) + Phenylephrine hydrochloride (10 mg/1)TabletOralNavajo Manuracturing Company2016-09-16Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
IbuprofenIbuprofen (200 mg/1)TabletOralRemedy Repack2010-12-082010-12-15Us
PrasteraIbuprofen (400 mg/1) + Prasterone (200 mg/1)KitOralHealth Science Funding, Llc2014-04-04Not applicableUs
Theraprofen-60Ibuprofen (600 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-07-19Not applicableUs
Theraprofen-800Ibuprofen (800 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-02-07Not applicableUs
Theraprofen-90Ibuprofen (600 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitPhysician Therapeutics Llc2011-02-07Not applicableUs
Topical PainIbuprofen (0.1 g/100mL) + Diazepam (0.1 g/100mL) + Hydrocodone (0.1 g/100mL) + Tramadol (0.1 g/100mL)CreamTopicalDr Marc's Manufacturing And Sales2016-02-232018-04-18Us
YbuphenIbuprofen (600 mg/1) + Acetaminophen (500 mg/1)KitOralAsclemed Usa, Inc.2018-11-01Not applicableUs
International/Other Brands
Act-3 (Healthcare Logistics) / Actiprofen (Sterling Health) / Adex (Dexxon) / Adran (Abbott) / Aktren (Bayer) / Alges-X (Axapharm) / Algoflex (Chinoin) / Algofren (Intermed) / Alivium (Bristol-Myers Squibb) / Artofen (Teva) / Betagesic (Adcock Ingram Pharmaceuticals) / Betaprofen (Be-Tabs Pharmaceuticals) / Bluton (Morishita) / Bonifen (Krka) / Brufen (Abbott) / Brupro (Sandoz) / Buburone (Towa Yakuhin) / Bugesic (Cipla Ltd) / Buprovil (Multilab Industry and Trade of Pharmaceuticals) / Burana (Orion) / Butylenin (Sanken) / Calprofen (McNeil) / Cap-Profen (PERRIGO) / Capsibu (Sandoz) / Children's Elixsure (Pfizer) / Children's Ibuprofen (Pfizer) / Dalsy (Abbott) / Dismenol (Merz) / Diverin (ACI Ltd) / Dolgirid (LGC) / Dolgit (Dolorgiet) / Dolofort (Fujisawa) / Doloraz (Jordanian Pharmaceutical Manufacturing Co.) / Dolormin (Johnson & Johnson GmbH) / Dorival / Ebufac (DDSA Pharmaceuticals) / EmuProfen (Progressive Emu, Inc) / Epobron (Ono) / Espidifen (Zambon) / Eve (Japan) / Femadon / Fenbid (Smith Kline and Beecham) / Fenpaed (Rite Aid Corporation) / Fenpain (Sandoz) / Finalflex / Galprofen (Walgreens) / Haltran / Herron Blue (Neurofen Australia) / i-profen (New Zealand) / Ibalgin (Zentiva) / Ibu-Attritin (LGC) / IBU-Ratiopharm (Ratiopharm GmbH) / Ibu-Vivimed / Ibuflam (Natco Pharma Ltd) / Ibugel (Dermal Laboratories Ltd) / Ibugesic (Cipra Ltd) / IbuHEXAL (Hexal AG) / Ibuleve (Diomed Development Ltd) / Ibum (PPF Hasco-Lek SA) / Ibumax (standford Biotech Pvt Ltd) / Ibumetin (Nycomed Denmark Aps) / Ibumidol / Ibupain (Sandoz) / Ibuprocin (Nisshin) / Ibuprom (USP Zdrowie) / Ibuprosyn / Ibuprox (Norway) / Ibustar (Berlin-Chemie Menarini Croatia) / Ibutid / Ibutren (Sandoz) / Ibux (Weifa AS) / Ibuxin (Pliva Hrvatska) / Inabrin / Inoven / Ipren / Junior Strength Motrin (J&J Consumer Inc) / Kratalgin (Austria) / Lamidon (Kowa) / Lebrufen / Liptan (Kowa) / Lotem (Adcock Ingram) / Medicol (United Lab) / Medipren (Johnson & Johnson) / Midol IB (Bayer) / Motrin (J&J Consumer Inc) / Mynosedin (Toho Yakuhin) / Mypaid (Ai Pharm) / Myprodol (Adcock Ingram) / Narfen (Alter) / Naron Ace (Primary Care Tokyo) / Neobrufen (Crookes) / Nobfen (Toho) / Nobgen (Toho) / Norvectan / Nuprin (Upjohn Company) / Nureflex (Boots Healthcare, Courbevoie) / Nurofen (Crookes) / Orbifen (Boehringer Ingelheim International GmbH) / Panafen (GlaxoSmithKline Consumer Healthcare Australia Pty Ltd) / Pediaprofen (Whitehall Laboratories) / Perifar / Profin / Ranfen / Rapidol (Actavis) / Ratiodolor / Rimafen / Roidenin (Showa) / Rufen (Boots) / Salvarina (Salvat, Barcelona) / Seclodin (Whitehall Labs, Maidenhead) / Solpaflex / Speedpain NANO (Goodsense) / Spidifen (Zambon) / Suspren / Tabalon (Sanofi India Ltd) / Tefin / Trendar (Whitehall-Robins) / Unafen / Upfen / Urem (Kade, MErlin)
Categories
UNII
WK2XYI10QM
CAS number
15687-27-1
Weight
Average: 206.2808
Monoisotopic: 206.13067982
Chemical Formula
C13H18O2
InChI Key
HEFNNWSXXWATRW-UHFFFAOYSA-N
InChI
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)
IUPAC Name
2-[4-(2-methylpropyl)phenyl]propanoic acid
SMILES
CC(C)CC1=CC=C(C=C1)C(C)C(O)=O

Pharmacology

Indication

Ibuprofen is the most commonly used and prescribed NSAID. It is very common over the counter medication widely used as an analgesic, anti-inflammatory and antipyretic.[11]

The use of ibuprofen and its enantiomer Dexibuprofen in a racemic mix is common for the management of mild to moderate pain related to dysmenorrhea, headache, migraine, postoperative dental pain, spondylitis, osteoarthritis, rheumatoid arthritis, and soft tissue disorder.[12]

Due to its activity against prostaglandin and thromboxane synthesis, ibuprofen has been attributed to alteration of platelet function and prolongation of gestation and labor.[10]

As ibuprofen is a widely used medication, the main therapeutic indications are:

  • Patent Ductus Arteriosus - it is a neonatal condition wherein the ductus arteriosus (blood vessel that connects the main pulmonary artery to the proximal descending aorta) fails to close after birth causing severe risk of heart failure. The prostaglandin inhibition of ibuprofen has been studied for the treatment of this condition as it is known that prostaglandin E2 is responsible for keeping the ductus arteriosus open.[13]

  • Rheumatoid- and osteo-arthritis - ibuprofen is very commonly used in the symptomatic treatment of inflammatory, musculoskeletal and rheumatic disorders.[14]

  • Cystic fibrosis - the use of high dosages of ibuprofen has been proven to decrease inflammation and decreasing polymorphonuclear cell influx in the lungs.[15]

  • Orthostatic hypotension - ibuprofen can induce sodium retention and antagonize the effect of diuretics which has been reported to be beneficial for patients with severe orthostatic hypotension.[1]

  • Dental pain - ibuprofen is used to manage acute and chronic orofacial pain.[16]

  • Minor pain - ibuprofen is widely used to reduce minor aches and pains as well as to reduce fever and manage dysmenorrhea. It is very commonly used for the relief of acute indications such as fever and tension headaches.[10]

  • Investigational uses - efforts have been put into developing ibuprofen for the prophylaxis of Alzheimer's disease, Parkinson disease, and breast cancer.[10]

Associated Conditions
Pharmacodynamics

Ibuprofen has multiple actions in different inflammatory pathways involved in acute and chronic inflammation. The main effects reported in ibuprofen are related to the control of pain, fever and acute inflammation by the inhibition of the synthesis of prostanoids by COX-1 and COX-2. Pain relief is attributed to peripheral affected regions and central nervous system effects in the pain transmission mediated by the dorsal horn and higher spinothalamic tract. Some reports have tried to link the pain regulation with a possible enhancement on the synthesis of endogenous cannabinoids and action on the NMDA receptors. The effect on pain has been shown to be related to the cortically evoked potentials.[23]

The antipyretic effect is reported to be linked to the effect on the prostanoid synthesis due to the fact that the prostanoids are the main signaling mediator of pyresis in the hypothalamic-preoptic region.[23]

The use of ibuprofen in dental procedures is attributed to the local inhibition of prostanoid production as well as to anti-oedemic activity and an increase of plasma beta-endorphins. Some reports have suggested a rapid local reduction of the expression of COX-2 in dental pulp derived by the administration of ibuprofen.[23]

The administration of ibuprofen in patients with rheumatic diseases has shown to control joint symptoms.[10]

Ibuprofen is largely used in OTC products such as an agent for the management of dysmenorrhea which has been proven to reduce the amount of menstrual prostanoids and to produce a reduction in the uterine hypercontractility.[17] As well, it has been reported to reduce significantly the fever and the pain caused by migraines.[18, 19] This effect is thought to be related to the effect on platelet activation and thromboxane A2 production which produces local vascular effects in the affected regions. This effect is viable as ibuprofen can enter in the central nervous system.[23]

In the investigational uses of ibuprofen, it has been reported to reduce neurodegeneration when given in low doses over a long time.[20] On the other hand, its use in Parkinson disease is related to the importance of inflammation and oxidative stress in the pathology of this condition.[21] The use of ibuprofen for breast cancer is related to a study that shows a decrease of 50% in the rate of breast cancer.[22]

Mechanism of action

The exact mechanism of action of ibuprofen is unknown. However, ibuprofen is considered an NSAID and thus it is a non-selective inhibitor of cyclooxygenase, which is an enzyme involved in prostaglandin (mediators of pain and fever) and thromboxane (stimulators of blood clotting) synthesis via the arachidonic acid pathway.[27]

Ibuprofen is a non-selective COX inhibitor and hence, it inhibits the activity of both COX-1 and COX-2. The inhibition of COX-2 activity decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling while the inhibition of COX-1 is thought to cause some of the side effects of ibuprofen including GI ulceration.[25]

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Human
AProstaglandin G/H synthase 1
inhibitor
Human
UApoptosis regulator Bcl-2
modulator
Human
UThrombomodulin
inducer
Human
UFatty acid-binding protein, intestinal
binder
Human
UPeroxisome proliferator-activated receptor gamma
activator
Human
UCystic fibrosis transmembrane conductance regulator
inhibitor
Human
UPeroxisome proliferator-activated receptor alpha
activator
Human
UPlatelet glycoprotein Ib alpha chain
inducer
Human
UProtein S100-A7
inducer
Human
Absorption

It is very well absorbed orally and the peak serum concentration can be attained in 1 to 2 hours after extravascular administration. When ibuprofen is administered immediately after a meal there is a slight reduction in the absorption rate but there is no change in the extent of the absorption.[10]

When orally administered, the absorption of ibuprofen in adults is very rapidly done in the upper GI tract.[23] The average Cmax, Tmax and AUC ranges around 20 mcg/ml, 2 h and 70 mcg.h/ml. These parameters can vary depending on the enantiomer form, route, and dose of administration.[23]

Volume of distribution

The apparent volume of distribution of ibuprofen is of 0.1 L/kg.[25]

Protein binding

Ibuprofen dosage is more than 99% bound to plasma proteins and site II of purified albumin, binding appears to be saturable and becomes non-linear at concentrations exceeding 20 mcg/ml.[10]

Metabolism

Ibuprofen is rapidly metabolized and biotransformed in the liver to the formation of major metabolites which are the hydroxylated and carboxylated derivatives.[10] As soon as it is absorbed, the R-enantiomer undergoes extensive enantiomeric conversion (53-65%) to the more active S-enantiomer in vivo by the activity of alpha-methylacyl-CoA racemase.[24]

Ibuprofen metabolism can be divided in phase I which is represented by the hydroxylation of the isobutyl chains for the formation of 2 or 3-hydroxy derivatives followed by oxidation to 2-carboxy-ibuprofen and p-carboxy-2-propionate. These oxidative reactions are performed by the activity of the cytochrome P450 isoforms CYP 2C9, CYP 2C19 and CYP 2C8. Therefore, these enzymes participate in the oxidation of the alkyl side chain to hydroxyl and carboxyl derivatives. From this enzymes, the major catalyst in the formation of oxidative metabolites is the isoform CYP 2C9.[23]

The metabolic phase I is followed by a phase II in which the oxidative metabolites may be conjugated to glucuronide prior to excretion. This activity forms phenolic and acyl glucuronides.[23]

Route of elimination

Ibuprofen is rapidly metabolized and eliminated in the urine thus, this via accounts for more than 90% of the administered dose. It is completely eliminated in 24 hours after the last dose and almost all the administered dose goes through metabolism, representing about 99% of the eliminated dose.[10] The biliary excretion of unchanged drug and active phase II metabolites represents 1% of the administered dose.[23]

In summary, ibuprofen is excreted as metabolites or their conjugates. The elimination of ibuprofen is not impaired by old age or the presence of renal impairment.[10]

Half life

The serum half-life of ibuprofen is 1.2-2 hours.[10] In patients with a compromised liver function, the half-life can be prolonged to 3.1-3.4 hours.[23]

Clearance

The clearance rate ranges between 3-13 L/h depending on the route of administration, enantiomer type and dosage.[23]

Toxicity

The symptoms of overdose are presented in individuals that consumed more than 99 mg/kg. 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).[26]

The reported LD50 of ibuprofen is of 636 mg/kg in rat, 740 mg/kg in mouse and 495 mg/kg in guinea pig.[MSDS]

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Ibuprofen Action PathwayDrug action
Ibuprofen Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Ibuprofen.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Ibuprofen.
AbacavirIbuprofen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Ibuprofen.
AbirateroneThe metabolism of Ibuprofen can be decreased when combined with Abiraterone.
AcarboseIbuprofen may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololIbuprofen may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Acemetacin.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Ibuprofen.
Food Interactions
  • 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.

References

General References
  1. Zawada ET Jr: Renal consequences of nonsteroidal antiinflammatory drugs. Postgrad Med. 1982 May;71(5):223-30. [PubMed:7041104]
  2. Townsend KP, Pratico D: Novel therapeutic opportunities for Alzheimer's disease: focus on nonsteroidal anti-inflammatory drugs. FASEB J. 2005 Oct;19(12):1592-601. [PubMed:16195368]
  3. Chen H, Jacobs E, Schwarzschild MA, McCullough ML, Calle EE, Thun MJ, Ascherio A: Nonsteroidal antiinflammatory drug use and the risk for Parkinson's disease. Ann Neurol. 2005 Dec;58(6):963-7. [PubMed:16240369]
  4. Geisslinger G, Dietzel K, Bezler H, Nuernberg B, Brune K: Therapeutically relevant differences in the pharmacokinetical and pharmaceutical behavior of ibuprofen lysinate as compared to ibuprofen acid. Int J Clin Pharmacol Ther Toxicol. 1989 Jul;27(7):324-8. [PubMed:2777420]
  5. Bergner T, Przybilla B: Photosensitization caused by ibuprofen. J Am Acad Dermatol. 1992 Jan;26(1):114-6. [PubMed:1531054]
  6. Dill J, Patel AR, Yang XL, Bachoo R, Powell CM, Li S: A molecular mechanism for ibuprofen-mediated RhoA inhibition in neurons. J Neurosci. 2010 Jan 20;30(3):963-72. doi: 10.1523/JNEUROSCI.5045-09.2010. [PubMed:20089905]
  7. Adams SS: The propionic acids: a personal perspective. J Clin Pharmacol. 1992 Apr;32(4):317-23. [PubMed:1569234]
  8. Rainsford KD: Discovery, mechanisms of action and safety of ibuprofen. Int J Clin Pract Suppl. 2003 Apr;(135):3-8. [PubMed:12723739]
  9. Halford GM, Lordkipanidze M, Watson SP: 50th anniversary of the discovery of ibuprofen: an interview with Dr Stewart Adams. Platelets. 2012;23(6):415-22. doi: 10.3109/09537104.2011.632032. Epub 2011 Nov 18. [PubMed:22098129]
  10. Bushra R, Aslam N: An overview of clinical pharmacology of Ibuprofen. Oman Med J. 2010 Jul;25(3):155-1661. doi: 10.5001/omj.2010.49. [PubMed:22043330]
  11. Adams SS, McCullough KF, Nicholson JS: The pharmacological properties of ibuprofen, an anti-inflammatory, analgesic and antipyretic agent. Arch Int Pharmacodyn Ther. 1969 Mar;178(1):115-29. [PubMed:5353466]
  12. Potthast H, Dressman JB, Junginger HE, Midha KK, Oeser H, Shah VP, Vogelpoel H, Barends DM: Biowaiver monographs for immediate release solid oral dosage forms: ibuprofen. J Pharm Sci. 2005 Oct;94(10):2121-31. doi: 10.1002/jps.20444. [PubMed:16136567]
  13. Sharma PK, Garg SK, Narang A: Pharmacokinetics of oral ibuprofen in premature infants. J Clin Pharmacol. 2003 Sep;43(9):968-73. [PubMed:12971028]
  14. Tan SC, Patel BK, Jackson SH, Swift CG, Hutt AJ: Ibuprofen stereochemistry: double-the-trouble? Enantiomer. 1999;4(3-4):195-203. [PubMed:10550887]
  15. Konstan MW, Krenicky JE, Finney MR, Kirchner HL, Hilliard KA, Hilliard JB, Davis PB, Hoppel CL: Effect of ibuprofen on neutrophil migration in vivo in cystic fibrosis and healthy subjects. J Pharmacol Exp Ther. 2003 Sep;306(3):1086-91. doi: 10.1124/jpet.103.052449. Epub 2003 Jun 13. [PubMed:12807998]
  16. Moore PA, Hersh EV: Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice. J Am Dent Assoc. 2001 Apr;132(4):451-6. [PubMed:11315375]
  17. Dawood MY: Primary dysmenorrhea: advances in pathogenesis and management. Obstet Gynecol. 2006 Aug;108(2):428-41. doi: 10.1097/01.AOG.0000230214.26638.0c. [PubMed:16880317]
  18. Krishna S, Pukrittayakamee S, Supanaranond W, ter Kuile F, Ruprah M, Sura T, White NJ: Fever in uncomplicated Plasmodium falciparum malaria: randomized double-'blind' comparison of ibuprofen and paracetamol treatment. Trans R Soc Trop Med Hyg. 1995 Sep-Oct;89(5):507-9. [PubMed:8560525]
  19. Evers S, Rahmann A, Kraemer C, Kurlemann G, Debus O, Husstedt IW, Frese A: Treatment of childhood migraine attacks with oral zolmitriptan and ibuprofen. Neurology. 2006 Aug 8;67(3):497-9. doi: 10.1212/01.wnl.0000231138.18629.d5. Epub 2006 Jun 14. [PubMed:16775229]
  20. Casper D, Yaparpalvi U, Rempel N, Werner P: Ibuprofen protects dopaminergic neurons against glutamate toxicity in vitro. Neurosci Lett. 2000 Aug 11;289(3):201-4. [PubMed:10961664]
  21. Ton TG, Heckbert SR, Longstreth WT Jr, Rossing MA, Kukull WA, Franklin GM, Swanson PD, Smith-Weller T, Checkoway H: Nonsteroidal anti-inflammatory drugs and risk of Parkinson's disease. Mov Disord. 2006 Jul;21(7):964-9. doi: 10.1002/mds.20856. [PubMed:16550541]
  22. Harris RE, Kasbari S, Farrar WB: Prospective study of nonsteroidal anti-inflammatory drugs and breast cancer. Oncol Rep. 1999 Jan-Feb;6(1):71-3. [PubMed:9864404]
  23. Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [PubMed:19949916]
  24. Tracy TS, Hall SD: Metabolic inversion of (R)-ibuprofen. Epimerization and hydrolysis of ibuprofenyl-coenzyme A. Drug Metab Dispos. 1992 Mar-Apr;20(2):322-7. [PubMed:1352228]
  25. Rao P, Knaus EE: Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond. J Pharm Pharm Sci. 2008 Sep 20;11(2):81s-110s. [PubMed:19203472]
  26. Hall AH, Smolinske SC, Conrad FL, Wruk KM, Kulig KW, Dwelle TL, Rumack BH: Ibuprofen overdose: 126 cases. Ann Emerg Med. 1986 Nov;15(11):1308-13. [PubMed:3777588]
  27. Current issues in pharmacy and medical sciences [Link]
External Links
Human Metabolome Database
HMDB0001925
KEGG Drug
D00126
KEGG Compound
C01588
PubChem Compound
3672
PubChem Substance
46507255
ChemSpider
3544
BindingDB
50009859
ChEBI
5855
ChEMBL
CHEMBL521
Therapeutic Targets Database
DAP000780
PharmGKB
PA449957
IUPHAR
2713
Guide to Pharmacology
GtP Drug Page
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RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ibuprofen
ATC Codes
M02AA13 — IbuprofenR02AX02 — IbuprofenC01EB16 — IbuprofenM01AE51 — Ibuprofen, combinationsM01AE01 — IbuprofenG02CC01 — Ibuprofen
AHFS Codes
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
FDA label
Download (1.77 MB)
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentFracture, Ankle1
0CompletedTreatmentPrimary Dysmenorrhoea1
0WithdrawnTreatmentPostoperative pain1
1CompletedNot AvailableAutonomic Failure / Idiopathic orthostatic hypotension1
1CompletedNot AvailableBioequivalence1
1CompletedNot AvailableHealthy Volunteers7
1CompletedBasic ScienceBioequivalence of the Test Formulation1
1CompletedBasic ScienceHealthy Volunteer Study2
1CompletedBasic ScienceHealthy Volunteers5
1CompletedBasic ScienceHealthy Volunteers / Inflammatory Reaction / Pain NOS1
1CompletedBasic ScienceInflammatory Reaction / Pain NOS1
1CompletedBasic SciencePain NOS4
1CompletedBasic SciencePharmacokinetics1
1CompletedDiagnosticOsteoarthritis (OA) / Osteoporosis1
1CompletedOtherModerate Pain1
1CompletedPreventionGastroduodenal Erosions1
1CompletedPreventionOther and unspecified effects of high altitude1
1CompletedSupportive CareBalanitis / Paraphimosis / Phimosis / Postoperative pain1
1CompletedTreatmentAllergic Rhinitis (AR)1
1CompletedTreatmentBioequivalency2
1CompletedTreatmentDuchenne's Muscular Dystrophy (DMD)1
1CompletedTreatmentHealthy Volunteers12
1CompletedTreatmentKnee Osteoarthritis (Knee OA)1
1CompletedTreatmentNSAID Related Gastric Irritation1
1CompletedTreatmentOsteoarthritis (OA)1
1CompletedTreatmentPain NOS1
1CompletedTreatmentSpinal Cord Injuries (SCI)1
1RecruitingTreatmentHealthy Volunteers1
1RecruitingTreatmentNeonates / Patent Ductus Arteriosus (PDA)1
1RecruitingTreatmentPatent Ductus Arteriosus (PDA)1
1TerminatedTreatmentHealthy Volunteers1
1Unknown StatusBasic ScienceKnee Osteoarthritis (Knee OA)1
1Unknown StatusBasic ScienceOther and unspecified effects of high altitude1
1Unknown StatusTreatmentAlzheimer's Disease (AD)1
1WithdrawnTreatmentTonsillectomy With or Without Adenoidectomy1
1, 2CompletedTreatmentTemporomandibular Joint Disorders1
1, 2Enrolling by InvitationPreventionAnalgesic Drugs / Pain Relief1
1, 2RecruitingTreatmentAdenotonsillectomy / Analgesia, Postoperative / Opioids Use1
1, 2RecruitingTreatmentCancer, Breast1
1, 2Unknown StatusTreatmentChoroidal Melanoma / Eye Neoplasms / Melanoma1
1, 2Unknown StatusTreatmentInfant, Extremely Premature / IV Ibuprofen / Oral Ibuprofen / Patent Ductus Arteriosus (PDA)1
2Active Not RecruitingTreatmentBronchopulmonary Dysplasia (BPD)1
2Active Not RecruitingTreatmentImpacted Wisdom Teeth1
2Active Not RecruitingTreatmentTuberculosis Infection1
2CompletedBasic ScienceSkeletal Muscle Mass Regulation1
2CompletedOtherComplication Due to Immunization1
2CompletedPreventionRetinopathy of Prematurity1
2CompletedSupportive CareStomatitis, Aphthous1
2CompletedTreatmentAcute Sore Throat Pain1
2CompletedTreatmentAdenoidectomy / Tonsillectomy1
2CompletedTreatmentCervical Strain1
2CompletedTreatmentContraception1
2CompletedTreatmentDelayed Onset Muscle Soreness1
2CompletedTreatmentDelayed Onset Muscle Soreness, DOMS1
2CompletedTreatmentDental Pain1
2CompletedTreatmentDiabetes, Diabetes Mellitus Type 11
2CompletedTreatmentDysmenorrhea1
2CompletedTreatmentIrreversible Pulpitis / Pain NOS / Postoperative pain1
2CompletedTreatmentMigraines1
2CompletedTreatmentOsteoarthritis (OA)1
2CompletedTreatmentPain NOS6
2CompletedTreatmentPain, Acute1
2CompletedTreatmentPost-Operative Pain1
2CompletedTreatmentPostoperative Dental Pain1
2CompletedTreatmentPostoperative pain1
2CompletedTreatmentSoft Tissue Injury1
2Enrolling by InvitationSupportive CareGingivostomatitis / Hand, Foot, and Mouth Disease / Herpangina1
2Not Yet RecruitingSupportive CareCarpal Tunnel Syndrome (CTS) / Cystic tumour of the ganglia / De Quervain's Disease / Dupuytren's Contracture of the Hand (Viking's Disease) / Trigger Digit1
2Not Yet RecruitingSupportive CarePostoperative pain1
2Not Yet RecruitingTreatmentChronic Lung Disease of Prematurity / Patent Ductus Arteriosus (PDA) / Preterm, Infant1
2Not Yet RecruitingTreatmentConcussion, Brain1
2Not Yet RecruitingTreatmentKnee Osteoarthritis (Knee OA)1
2RecruitingBasic ScienceChronic Granulomatous Disease X-linked (X-CGD)1
2RecruitingPreventionAnalgesia1
2RecruitingPreventionFertilization in Vitro/Methods / Ovulation / Ovulation Inhibition / Ovulation Inhibition/Drug Effects / Pregnancy1
2RecruitingPreventionPost-ERCP Acute Pancreatitis1
2RecruitingSupportive CareCognitive Impairments / Stage 0 Colorectal Cancer / Stage I Colorectal Cancer / Stage II Colorectal Cancer / Stage IIA Colorectal Cancer / Stage IIB Colorectal Cancer / Stage IIC Colorectal Cancer / Stage III Colorectal Cancer / Stage IIIA Colorectal Cancer / Stage IIIB Colorectal Cancer / Stage IIIC Colorectal Cancer1
2RecruitingTreatmentAcute Gouty Arthritis1
2RecruitingTreatmentCancer-related Cognitive Difficulties1
2RecruitingTreatmentComatose / Hyperpyrexia / Parasitemia / Plasmodium Infections / Seizures1
2RecruitingTreatmentGeneral Surgery1
2RecruitingTreatmentPain Management1
2RecruitingTreatmentPatent Ductus Arteriosus (PDA)1
2RecruitingTreatmentSunburn1
2RecruitingTreatmentPainful musculoskeletal conditions1
2TerminatedTreatmentCervical Spondylosis / Lumbar Spondylosis1
2TerminatedTreatmentPost-surgical Dental Pain1
2TerminatedTreatmentPostsurgical Pain Due to Third Molar Extraction1
2Unknown StatusPreventionPost Bronchoscopy Fever1
2Unknown StatusPreventionSpectrum of Altitude-associated Neurologic Forms of Altitude1
2Unknown StatusSupportive CareMetastatic Cancers1
2Unknown StatusTreatmentImpacted Third Molar Tooth1
2WithdrawnTreatmentDental Pain1
2WithdrawnTreatmentHb-SS Disease With Vasoocclusive Pain / Hemoglobin SS Disease With Crisis / Hemoglobin SS Disease With Vasoocclusive Crisis / Other Sickle Cell Disease With Vaso-Occlusive Pain / Sickle Cell Disorders1
2WithdrawnTreatmentPatent Ductus Arteriosus (PDA)1
2, 3CompletedBasic ScienceMajor Depressive Disorder (MDD)1
2, 3CompletedSupportive CareHigh Blood Pressure (Hypertension)1
2, 3CompletedTreatmentBack Pain Lower Back1
2, 3CompletedTreatmentCervicobrachial Neuralgia1
2, 3CompletedTreatmentIdiopathic Intracranial Hypertension (IIH)1
2, 3CompletedTreatmentPatent Ductus Arteriosus (PDA)1
2, 3RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
2, 3RecruitingTreatmentHemodynamically Significant Patent Ductus Arteriosus in Preterm Infants / Patent Ductus Arteriosus (PDA)1
2, 3RecruitingTreatmentPatent Ductus Arteriosus (PDA) / Respiratory Distress Syndrome (RDS)1
3Active Not RecruitingTreatmentAcute Ankle Sprain1
3Active Not RecruitingTreatmentPatent Ductus Arteriosus (PDA)1
3CompletedNot AvailablePain NOS1
3CompletedPreventionAcute Kidney Injury (AKI) / Exercise-associated Hyponatremia / Perceived Exertion1
3CompletedPreventionAltitude Sickness1
3CompletedPreventionBack Pain Lower Back Chronic / Chronic Regional Pain Syndrome / Chronic Soft Tissue Pain / Osteoarthritis (OA) / Rheumatoid Arthritis1
3CompletedPreventionIUD Removal1
3CompletedPreventionPeptic Ulcers1
3CompletedPreventionUlcers1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentAcute Respiratory Distress Syndrome (ARDS) / Chronic Lung Diseases / Shock, Septic1
3CompletedTreatmentAcute Sore Throat Pain1
3CompletedTreatmentAsthma Bronchial / Wheezing1
3CompletedTreatmentBack Pain Lower Back1
3CompletedTreatmentBack Pain / Cervical Pain1
3CompletedTreatmentDelayed Onset Muscle Soreness, DOMS1
3CompletedTreatmentDental Pain1
3CompletedTreatmentDysmenorrhea1
3CompletedTreatmentFevers4
3CompletedTreatmentFevers / Respiratory Tract Infections (RTI)1
3CompletedTreatmentForearm Fractures1
3CompletedTreatmentModerate or Severe Submental Fullness1
3CompletedTreatmentOsteoarthritis (OA)1
3CompletedTreatmentPain NOS9
3CompletedTreatmentPain NOS / Post-Operative Pain / Third Molar Extraction1
3CompletedTreatmentPain NOS / Pregnancy1
3CompletedTreatmentPatent Ductus Arteriosus (PDA)2
3CompletedTreatmentPost Operative Dental Pain1
3CompletedTreatmentPost Operative Pain1
3CompletedTreatmentPost-Operative Pain1
3CompletedTreatmentPost-surgical Pain Following Extraction of Molar Teeth1
3CompletedTreatmentPostoperative Dental Pain1
3CompletedTreatmentPostoperative pain1
3CompletedTreatmentPostoperative pain / Tooth Diseases1
3CompletedTreatmentPrimary Dysmenorrhoea1
3CompletedTreatmentTonsillectomy1
3CompletedTreatmentMinor burns1
3Not Yet RecruitingTreatmentAtopic Dermatitis (AD)1
3Not Yet RecruitingTreatmentBack Pain Lower Back1
3Not Yet RecruitingTreatmentCold1
3Not Yet RecruitingTreatmentHernia / Pain NOS1
3Not Yet RecruitingTreatmentPostoperative pain / Radical Prostatectomy1
3Not Yet RecruitingTreatmentVasculitis1
3RecruitingSupportive CareMalignant Head and Neck Neoplasm / Mucositis / Radiation-Induced Disorder1
3RecruitingTreatmentAcute Musculoskeletal Disease / Emergency / Pain, Acute / Sprains / Sprains and Strains / Traumas / Traumatic Injuries1
3RecruitingTreatmentAlzheimer's Disease (AD)1
3RecruitingTreatmentLong-bone Fractures / Pain NOS1
3RecruitingTreatmentPatent Ductus Arteriosus (PDA)1
3RecruitingTreatmentPostoperative pain / Surgery, Outpatient1
3TerminatedTreatmentCerebral Palsy (CP)1
3TerminatedTreatmentDysmenorrhea1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentInfection NOS1
3TerminatedTreatmentModerate to Severe Primary Dysmenorrhea1
3TerminatedTreatmentPostoperative pain1
3Unknown StatusSupportive CarePostoperative pain1
3Unknown StatusTreatmentHeadaches1
3Unknown StatusTreatmentMuscular Atrophy / Sprains / Tendonitis1
3Unknown StatusTreatmentNeoplasms, Breast1
3Unknown StatusTreatmentPediatric Obstructive Sleep Apnea Syndrome1
3WithdrawnTreatmentOsteoarthritis (OA)1
3WithdrawnTreatmentPain NOS1
3WithdrawnTreatmentAcute Rhinitis1
4Active Not RecruitingPreventionPain, Acute / Postoperative pain1
4Active Not RecruitingTreatmentEclampsia / HELLP Syndrome / Prophylaxis of preeclampsia1
4Active Not RecruitingTreatmentPatent Ductus Arteriosus (PDA)1
4CompletedNot AvailablePatent Ductus Arteriosus (PDA) / Prematurity of Fetus1
4CompletedBasic ScienceHealthy Volunteers2
4CompletedBasic ScienceIschaemic Heart Diseases / Osteoarthritis (OA)1
4CompletedBasic SciencePain NOS1
4CompletedHealth Services ResearchPain NOS1
4CompletedPreventionAcute Mountain Sickness, Blood Oxygen Saturation, Headache1
4CompletedPreventionArthroplasty, Replacement, Hip / Osteoarthritis, Hip / Rheumatoid Arthritis1
4CompletedPreventionOsteoarthritis (OA) / Rheumatoid Arthritis1
4CompletedPreventionPain Measurement1
4CompletedPreventionRecurrence of Febrile Seizure1
4CompletedPreventionStreptococcal Infections1
4CompletedPreventionVaccines, Pneumococcal1
4CompletedSupportive CareCongenital Muscular Torticollis1
4CompletedSupportive CareOrthodontic Pain1
4CompletedSupportive CarePain NOS1
4CompletedSupportive CarePain NOS / Pituitary Neoplasms1
4CompletedSupportive CareSymptomatic Uterine Fibroids and Adenomyosis1
4CompletedTreatmentAcne Vulgaris1
4CompletedTreatmentAcute Cystitis (Excl in Pregnancy)1
4CompletedTreatmentAlzheimer's Disease (AD)1
4CompletedTreatmentAnalgesia / Postoperative pain1
4CompletedTreatmentAnalgesics1
4CompletedTreatmentArthroscopic Knee Surgery1
4CompletedTreatmentBMI >30 kg/m21
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentBack Pain Lower Back Chronic1
4CompletedTreatmentBariatric Surgery Candidate / Obesity, Morbid1
4CompletedTreatmentBreast Pain1
4CompletedTreatmentCarpal Tunnel / Cystic tumour of the ganglia / De Quervain's Disease / Trigger Finger1
4CompletedTreatmentDental Pain1
4CompletedTreatmentFeeling Anxious / Nausea / Pain NOS1
4CompletedTreatmentFevers3
4CompletedTreatmentFevers / Pain NOS1
4CompletedTreatmentFracture Bone1
4CompletedTreatmentGallbladder disorders1
4CompletedTreatmentGastrointestinal Mucosal Damage1
4CompletedTreatmentGeneral Surgery1
4CompletedTreatmentHeadache, Tension-Type / Headaches / Tension-Type Headache (Episodic)1
4CompletedTreatmentHeat / Pain NOS1
4CompletedTreatmentHigh Blood Pressure (Hypertension)1
4CompletedTreatmentHypertension, Pregnancy-Induced / Prophylaxis of preeclampsia1
4CompletedTreatmentImpaired Renal Function / Myocardial Infarction / Postoperative pain1
4CompletedTreatmentInfants, Premature / Patent Ductus Arteriosus (PDA)1
4CompletedTreatmentIrreversible Pulpitis1
4CompletedTreatmentJuvenile Idiopathic Arthritis (JIA)1
4CompletedTreatmentKnee Osteoarthritis (Knee OA)4
4CompletedTreatmentMigrainous Headache1
4CompletedTreatmentMosquito Bites1
4CompletedTreatmentMuscle Soreness1
4CompletedTreatmentNSAIDs / Pain Management1
4CompletedTreatmentNarcotic Use / Nausea / Occasional Constipation / Pain NOS1
4CompletedTreatmentOpioids Use / Postoperative pain1
4CompletedTreatmentOsteoarthritis of the Hip or Knee1
4CompletedTreatmentPain NOS8
4CompletedTreatmentPain, Acute1
4CompletedTreatmentPatent Ductus Arteriosus (PDA)2
4CompletedTreatmentPostoperative pain4
4CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
4CompletedTreatmentRheumatoid Arthritis1
4CompletedTreatmentRotator Cuff Syndrome1
4CompletedTreatmentTraumas1
4CompletedTreatmentUrinary Tract Infections (UTIs)1
4Enrolling by InvitationSupportive CareColectomy / Opioids Use / Postoperative pain / Surgery, Colorectal1
4Not Yet RecruitingDiagnosticChronic Renal Failure (CRF)1
4Not Yet RecruitingTreatmentAnalgesia / Percutaneous Nephrolithotomy1
4Not Yet RecruitingTreatmentAnalgesics, Opioid / Anti-Inflammatory Agents, Non-Steroidal / Child/Adolescent Problems / Emergency Service, Hospital / Fentanyl / Ibuprofen / Pain, Acute1
4Not Yet RecruitingTreatmentBack Pain Lower Back1
4Not Yet RecruitingTreatmentDistal Radius Fractures / Metacarpal Fractures / Pain Management1
4Not Yet RecruitingTreatmentOpioids Use / Postoperative pain / Quality of Life1
4Not Yet RecruitingTreatmentPain NOS1
4Not Yet RecruitingTreatmentPain, Acute1
4Not Yet RecruitingTreatmentPostoperative pain / Rotator Cuff Syndrome1
4RecruitingPreventionAnaesthesia therapy / Hip Fractures1
4RecruitingScreeningPhrenic Nerve Paralysis1
4RecruitingSupportive CareCarpal Tunnel1
4RecruitingSupportive CareImpacted Third Molar Tooth / Other Surgical Procedures / Pain NOS1
4RecruitingTreatmentAbortion Second Trimester1
4RecruitingTreatmentAcute Diverticulitis1
4RecruitingTreatmentAcute Kidney Injury (AKI) / Impaired Renal Function / Pharmacokinetics / Renal Failure1
4RecruitingTreatmentCervical Preparation / Pain NOS / Pregnancy Termination1
4RecruitingTreatmentEpisodic Migraine1
4RecruitingTreatmentFevers / Pain NOS1
4RecruitingTreatmentFlu caused by Influenza1
4RecruitingTreatmentLumbar Disc Disease / Lumbar Radiculopathy / Prolapsed Lumbar Disc1
4RecruitingTreatmentLung Cancers1
4RecruitingTreatmentPain NOS1
4RecruitingTreatmentPost-Cesarean Section / Postoperative pain1
4RecruitingTreatmentPostoperative pain3
4RecruitingTreatmentRib Fracture Multiple / Rib Fractures1
4RecruitingTreatmentRib Fractures / Wounds and Injuries1
4RecruitingTreatmentSciatica1
4RecruitingTreatmentSickle Cell Anemia Crisis1
4SuspendedTreatmentRotator Cuff Syndrome1
4TerminatedPreventionHeart Transplantation / Transplantation, Kidney / Transplantation, Liver1
4TerminatedPreventionHigh Blood Pressure (Hypertension)1
4TerminatedTreatmentAdverse Reaction to Drug / Obstructive Sleep Apnea (OSA) / Recurrent Tonsillitis / Sleep Disordered Breathing (SDB)1
4TerminatedTreatmentAnalgesia / Aspiration / Pain NOS / Tibial Fractures1
4TerminatedTreatmentDepression / Depression, Myalgia1
4TerminatedTreatmentHematologic Diseases / Sickle Cell Disorders1
4TerminatedTreatmentInflammatory Responses1
4TerminatedTreatmentPain NOS1
4TerminatedTreatmentPatent Ductus Arteriosus (PDA)1
4TerminatedTreatmentPeriodontitis1
4TerminatedTreatmentSickle Cell Disorders1
4Unknown StatusDiagnosticPatent Ductus Arteriosus (PDA)1
4Unknown StatusSupportive CareChronic Pelvic Pain1
4Unknown StatusTreatmentDental Extraction1
4Unknown StatusTreatmentFevers3
4Unknown StatusTreatmentPharyngitis1
4WithdrawnTreatmentArthritic Knee Pain1
4WithdrawnTreatmentPatent Ductus Arteriosus (PDA) / Very Low Birth Weight Infants1
Not AvailableActive Not RecruitingNot AvailableAdverse Events / Drug Overdose1
Not AvailableActive Not RecruitingTreatmentColles Fracture1
Not AvailableActive Not RecruitingTreatmentFlail Chest / General Surgery / Rib Fractures / Traumas1
Not AvailableCompletedNot AvailableAging / Physical Fitness1
Not AvailableCompletedNot AvailableConcussions / Headaches1
Not AvailableCompletedBasic ScienceAsthma, Allergic1
Not AvailableCompletedBasic ScienceBMI >30 kg/m21
Not AvailableCompletedBasic ScienceIschemic Reperfusion Injury1
Not AvailableCompletedBasic SciencePlatelet Aggregation1
Not AvailableCompletedBasic ScienceStability & Variability of Lipid-derived Molecules in Sweat1
Not AvailableCompletedDiagnosticDermatitis, Photocontact1
Not AvailableCompletedOtherAnti Inflammatory Non-Steroidal / Cystic Fibrosis (CF) / Neutrophils1
Not AvailableCompletedOtherLocal Anesthesia1
Not AvailableCompletedPreventionCardiovascular Disease (CVD)1
Not AvailableCompletedPreventionOsteoporosis / Sarcopenia1
Not AvailableCompletedPreventionPostoperative pain1
Not AvailableCompletedPreventionPostoperative pain / Wisdom Tooth1
Not AvailableCompletedSupportive CareElbow Fractures1
Not AvailableCompletedSupportive CareHyperalgesia / Ibuprofen / Postoperative pain / Remifentanil1
Not AvailableCompletedSupportive CareInfertilities / Subfertility1
Not AvailableCompletedSupportive CareRespiration Disorders1
Not AvailableCompletedTreatmentAnalgesia Post Fracture / Upper Extremity Fractures1
Not AvailableCompletedTreatmentBack Pain Lower Back1
Not AvailableCompletedTreatmentCancer, Breast1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)2
Not AvailableCompletedTreatmentDiverticulitis1
Not AvailableCompletedTreatmentDysmenorrhea1
Not AvailableCompletedTreatmentFracture Bone1
Not AvailableCompletedTreatmentGlaucoma / Ocular Hypertension1
Not AvailableCompletedTreatmentHemophilia A / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHernia, Abdominal / Inguinal Hernias / Laparoscopic Cholecystectomy / Umbilical Hernias1
Not AvailableCompletedTreatmentHypoxic Ischemic Encephalopathy (HIE) / Perinatal Asphyxia1
Not AvailableCompletedTreatmentInduction of Labour1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)4
Not AvailableCompletedTreatmentMusculoskeletal Injuries1
Not AvailableCompletedTreatmentPain NOS3
Not AvailableCompletedTreatmentPatent Ductus Arteriosus (PDA)3
Not AvailableCompletedTreatmentPneumonia1
Not AvailableCompletedTreatmentPostoperative Pain Management1
Not AvailableCompletedTreatmentPostoperative pain1
Not AvailableCompletedTreatmentSkin Laxity1
Not AvailableCompletedTreatmentSpinal Stenosis of Lumbar Region1
Not AvailableCompletedTreatmentSpondyloarthritis, Axial1
Not AvailableCompletedTreatmentTemporomandibular Disorders1
Not AvailableEnrolling by InvitationOtherKnee Osteoarthritis (Knee OA)1
Not AvailableNot Yet RecruitingTreatmentDysmenorrhea1
Not AvailableNot Yet RecruitingTreatmentInguinal Hernias1
Not AvailableRecruitingNot AvailableMultimodal Analgesia / Nonsteroidal Anti-inflammatory Drugs1
Not AvailableRecruitingPreventionCachexia / Neoplasms1
Not AvailableRecruitingPreventionDisorder of Urinary Stent / Ureteral Spasm / Ureteropelvic Junction Obstruction / Urolithiasis1
Not AvailableRecruitingPreventionImmune System and Related Disorders1
Not AvailableRecruitingTreatmentBiliary Colic1
Not AvailableRecruitingTreatmentHigh Altitude Headache / Other and unspecified effects of high altitude1
Not AvailableRecruitingTreatmentHypertension, Pregnancy-Induced1
Not AvailableRecruitingTreatmentInguinal Surgery1
Not AvailableRecruitingTreatmentPatent Ductus Arteriosus (PDA)2
Not AvailableRecruitingTreatmentRotator Cuff Tear Arthropathy1
Not AvailableSuspendedTreatmentLaceration / Pain NOS1
Not AvailableTerminatedOtherHealthy Volunteers1
Not AvailableTerminatedPreventionPain NOS1
Not AvailableTerminatedTreatmentCachexia / Cancer, Advanced1
Not AvailableTerminatedTreatmentInfants, Premature / Patent Ductus Arteriosus (PDA)1
Not AvailableTerminatedTreatmentPain, Chronic1
Not AvailableTerminatedTreatmentPatent Ductus Arteriosus (PDA) / Preterm, Infant1
Not AvailableTerminatedTreatmentSevere Traumatic Brain Injury / Subarachnoid Hemorrhage1
Not AvailableTerminatedTreatmentSoft Tissue Injury1
Not AvailableUnknown StatusNot AvailableFevers1
Not AvailableUnknown StatusBasic ScienceMalignant Neoplasm of Colon1
Not AvailableUnknown StatusPreventionOral Ibuprofen Prophylaxis in Very Low Birth Weight Infants1
Not AvailableUnknown StatusSupportive CarePrimary Post Tonsillectomy Hemorrhage / Secondary Post Tonsillectomy Hemorrhage1
Not AvailableUnknown StatusTreatmentFevers1
Not AvailableUnknown StatusTreatmentFracture Bone / Pain NOS1
Not AvailableUnknown StatusTreatmentPain NOS1
Not AvailableUnknown StatusTreatmentPleuro-pneumonia1
Not AvailableWithdrawnSupportive CareToothache1
Not AvailableWithdrawnTreatmentPsychiatric Disorder NOS1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Abbott Laboratories Ltd.
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Altura Pharmaceuticals Inc.
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • Apothecary Shop Wholesale
  • A-S Medication Solutions LLC
  • Ascend Laboratories LLC
  • Atlantic Biologicals Corporation
  • BASF Corp.
  • Bayer Healthcare
  • Ben Venue Laboratories Inc.
  • Blenheim Pharmacal
  • Breckenridge Pharmaceuticals
  • Bryant Ranch Prepack
  • Bv Pharbita
  • Cardinal Health
  • Caremark LLC
  • Central Texas Community Health Centers
  • Centrix Pharmaceuticals
  • Chain Drug
  • Corepharma LLC
  • Coupler Enterprises Inc.
  • Cumberland Pharmaceuticals
  • CVS Pharmacy
  • Darby Dental Supply Co. Inc.
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Dorx LLC
  • Eckerd
  • Equaline Vitamins
  • Gm Pharmaceuticals Inc.
  • Golden State Medical Supply Inc.
  • Greenstone LLC
  • Group Health Cooperative
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Hawthorn Pharmaceuticals
  • Heartland Repack Services LLC
  • Hl Moore Drug Exchange
  • Imiren Pharmaceuticals Inc.
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Keltman Pharmaceuticals Inc.
  • Kowa Pharmaceuticals America Inc.
  • Lake Erie Medical and Surgical Supply
  • LeaderPharma
  • Legacy Pharmaceuticals Packaging LLC
  • Liberty Pharmaceuticals
  • Lundbeck Inc.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • McNeil Laboratories
  • Medicine Shop
  • Medique Products
  • Medisca Inc.
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Particle Dynamics Co.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmaceutical Association
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacia Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Poly Pharmaceuticals Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Prescription Dispensing Service Inc.
  • Publix Super Markets
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Rite Aid Corp.
  • Sandhills Packaging Inc.
  • Shanghai Ziyuan Pharmaceutical Co. Ltd.
  • Shasun Chemicals & Drugs Ltd.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Sunmark
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Ultras Pharmaceuticals Inc.
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Veratex Corp.
  • Vintage Pharmaceuticals Inc.
  • Vistapharm Inc.
  • Walgreen Co.
  • Watson Pharmaceuticals
  • Wyeth Pharmaceuticals
  • Xactdose Inc.
Dosage forms
FormRouteStrength
Kit
KitTopical
Tablet, extended releaseOral600 mg
CapsuleOral
TabletOral
Capsule; kitOral
CapsuleOral400 mg
CapsuleOral200 mg
Tablet, coatedOral256 mg/1
TabletOral400 mg/400mg
TabletOral600 mg/600mg
TabletOral800 mg/800mg
TabletOral300 mg
TabletOral600 mg
TabletOral200 mg
InjectionIntravenous800 mg/8mL
SolutionIntravenous100 mg
SuspensionOral100 mg
Tablet, chewableOral50 mg
SuspensionOral
TabletOral50 mg
SolutionOral100 mg/5mL
SuspensionOral200 mg/10mL
Suspension / dropsOral100 mg/5mL
Kit; tabletOral
Kit800 mg/1
Tablet, film coatedOral256 mg/1
Capsule, liquid filledOral200 mg/1
SuspensionOral50 mg/1.25mL
Tablet, film coatedOral
Capsule, coatedOral200 mg/1
LiquidOral100 mg/5mL
SuspensionOral100 mg/5mL
Suspension / dropsOral50 mg/1.25mL
TabletOral200 mg/1
TabletOral400 mg/1
TabletOral600 mg/1
TabletOral800 1/1
TabletOral800 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral400 mg/1
Tablet, coatedOral600 mg/1
Tablet, coatedOral800 mg/1
Tablet, film coatedOral200 1/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral200 mg/1 1
Tablet, film coatedOral400 mg/1
Tablet, film coatedOral400 mg/400mg
Tablet, film coatedOral400 mg/301
Tablet, film coatedOral600 mg/600mg
Tablet, film coatedOral600 mg/1
Tablet, film coatedOral800 mg/800mg
Tablet, film coatedOral800 mg/1
Tablet, sugar coatedOral200 mg/1
Tablet, sugar coatedOral
CapsuleOral200 mg/1
Capsule, liquid filledOral
SuspensionOral40 mg
KitOral; Topical
Tablet, chewableOral100 mg
Tablet, coatedOral100 mg/1
TabletOral100 mg
Tablet, chewableOral100 mg/1
Tablet, film coatedOral100 mg/1
Injection, solutionIntravenous10 mg/1mL
SolutionIntravenous10 mg/1mL
Injection, solutionIntravenous5 mg/ml
LiquidOral50 mg/1.25mL
Kit600 mg/1
TabletOral400 mg
KitOral
TabletOral400 mg/537mg
Tablet, film coatedOral200 1/2001
CreamTopical
KitOral600 mg/1
Tablet, coatedOral
Prices
Unit descriptionCostUnit
Neoprofen 20 mg/2 ml vial304.5USD ml
Caldolor 400 mg/4 ml vial2.21USD ml
Caldolor 800 mg/8 ml vial1.58USD ml
Nuprin arthritis patch1.11USD patch
Ibuprofen powder1.04USD g
Nuprin muscle & joint patch1.03USD patch
Profen II 45-800 mg 12 Hour tablet0.69USD tablet
Motrin 800 mg tablet0.59USD tablet
Advil allergy sinus caplet0.5USD caplet
Ibu-drops 40 mg/ml suspension drops0.42USD ml
Motrin 600 mg tablet0.4USD tablet
Ibuprofen 800 mg tablet0.36USD tablet
Ibuprofen 400 mg tablet0.35USD tablet
Infant's motrin 50 mg/1.25 ml0.34USD ml
Childs ibuprofen susp drp0.33USD ml
Ibuprofen 600 mg tablet0.33USD tablet
Wal-profen cold & sinus cplt0.3USD caplet
Infant ibuprofen susp drop0.29USD ml
Motrin 400 mg tablet0.29USD tablet
CVS Pharmacy infant ibuprofen susp drop0.25USD ml
Infants medi-profen susp0.23USD ml
Advil cold & sinus caplet0.22USD caplet
Advil pm caplet0.22USD caplet
Soba profen cold-sinus tablet0.22USD tablet
Midol caplet0.21USD caplet
Advil migraine 200 mg capsule0.2USD capsule
Ibuprofen cold-sinus caplet0.2USD caplet
Motrin 100 mg caplet0.2USD caplet
Motrin pm caplet0.2USD caplet
Advil 200 mg liqui-gel capsule0.19USD capsule
Soba profen ib caplet0.19USD caplet
Motrin 100 mg tablet chew0.18USD tablet
Pub infants profenib drops0.18USD ml
Sm ibuprofen ib 100 mg tablet0.18USD tablet
Eck ibuprofen jr caplet0.17USD caplet
Ibuprofen pm caplet0.17USD caplet
Advil 200 mg caplet0.15USD capsule
Advil 200 mg gel caplet0.15USD caplet
Advil 200 mg tablet0.15USD tablet
Ibuprofen 100 mg tablet chew0.15USD tablet
Motrin ib 200 mg caplet0.15USD caplet
Apo-Ibuprofen 600 mg Tablet0.14USD tablet
CVS Pharmacy ibuprofen jr str 100 mg tablet0.14USD tablet
Nu-Ibuprofen 600 mg Tablet0.14USD tablet
Motrin ib 200 mg tablet0.13USD tablet
Motrin ib 200 mg gelcap0.12USD capsule
Nuprin 200 mg caplet0.12USD caplet
Wal-profen 200 mg caplet0.12USD caplet
Wal-profen 200 mg tablet0.12USD tablet
Eql ibuprofen 200 mg tablet0.1USD tablet
Nuprin 200 mg tablet0.1USD tablet
Apo-Ibuprofen 400 mg Tablet0.08USD tablet
Ibuprofen ib 200 mg tablet0.08USD tablet
Novo-Profen 400 mg Tablet0.08USD tablet
Apo-Ibuprofen 300 mg Tablet0.07USD tablet
Medi-profen 200 mg tablet0.07USD tablet
Ibuprofen 100 mg/5ml Suspension0.06USD ml
Ibuprofen 200 mg caplet0.06USD caplet
Child ibuprofen susp0.05USD ml
Children's medi-profen susp0.05USD ml
Children's motrin cold suspension0.05USD ml
CVS Pharmacy ibuprofen 200 mg tablet0.05USD tablet
Ibuprofen cold suspension0.05USD ml
I-prin 200 mg tablet0.05USD tablet
Novo-Profen 600 mg Tablet0.05USD tablet
Children's motrin cold0.04USD ml
Pv ibuprofen 200 mg caplet0.04USD caplet
Soba children's profenib susp0.04USD ml
Ibuprofen 200 mg tablet0.03USD tablet
CVS Pharmacy ibuprofen 200 mg caplet0.02USD caplet
Pv ibuprofen 200 mg tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5215755No1993-06-012010-06-01Us
US6599531No2003-07-292017-06-10Us
US6348216No2002-02-192017-06-10Us
US6342530No2002-01-292020-11-14Us
US6344479No2002-02-052021-03-20Us
US8415337No2013-04-092032-03-02Us
US6211246No2001-04-032019-06-10Us
US8883849No2014-11-112022-01-17Us
US9155718No2015-10-132022-01-17Us
US8263647No2012-09-112022-05-30Us
US7863287No2011-01-042027-02-28Us
US6251426No2001-06-262018-06-25Us
US6727286No2004-04-272021-11-27Us
US8735452No2014-05-272029-09-30Us
US9138404No2015-09-222029-09-30Us
US9114068No2015-08-252029-09-30Us
US8871810No2014-10-282029-09-30Us
US9012508No2015-04-212030-09-14Us
US9295639No2016-03-292029-09-30Us
US8067451No2011-11-292026-07-18Us
US8501228No2013-08-062026-07-18Us
US8318202No2012-11-272026-07-18Us
US8449910No2013-05-282026-07-18Us
US8309127No2012-11-132026-07-18Us
US8067033No2011-11-292026-07-18Us
US9649284No2017-05-162029-09-30Us
US9072710No2015-07-072032-03-16Us
US9072661No2015-07-072032-03-16Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)75-77.5 ºCU.S. Patent 3,228,831 U.S. Patent 3,385,886
boiling point (°C)157 ºC'AlfaAesar MSDS'
water solubility21 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.97AVDEEF,A (1997)
logS-3.99ADME Research, USCD
Caco2 permeability-4.28ADME Research, USCD
pKa5.3Bushra and Aslam. Oman Med. 25, 3. (2010)
Predicted Properties
PropertyValueSource
Water Solubility0.0684 mg/mLALOGPS
logP3.5ALOGPS
logP3.84ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.85ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity60.73 m3·mol-1ChemAxon
Polarizability23.76 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9927
Blood Brain Barrier+0.9619
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.759
P-glycoprotein inhibitor INon-inhibitor0.9705
P-glycoprotein inhibitor IINon-inhibitor0.9323
Renal organic cation transporterNon-inhibitor0.9323
CYP450 2C9 substrateNon-substrate0.7594
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6877
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9305
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9881
CYP450 3A4 inhibitorNon-inhibitor0.9655
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9691
Ames testNon AMES toxic0.9894
CarcinogenicityCarcinogens 0.5553
BiodegradationReady biodegradable0.5142
Rat acute toxicity2.3092 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9719
hERG inhibition (predictor II)Non-inhibitor0.9734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.4 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-02t9-1910000000-23f448d7be7d5cc35682
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-02t9-1910000000-cbe52d63986b68a2cec0
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)GC-MSsplash10-00di-9300000000-cc259b7768023e4cdba8
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03di-3910000000-618880f8fd7b8ec3d473
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-02t9-1910000000-23f448d7be7d5cc35682
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-02t9-1910000000-cbe52d63986b68a2cec0
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9300000000-cc259b7768023e4cdba8
Mass Spectrum (Electron Ionization)MSsplash10-03xr-3900000000-e20ef3c30496e17720ba
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-03di-0910000000-90bf6813134491c9fbfd
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-001i-9800000000-56f599abc462380b648c
MS/MS Spectrum - EI-B (HITACHI RMU-6E) , PositiveLC-MS/MSsplash10-03di-3910000000-618880f8fd7b8ec3d473
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1900000000-f1b7a986fee133d97eb1
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0920000000-aa36b3244e32560bb9d5
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Phenylpropanoic acids
Sub Class
Not Available
Direct Parent
Phenylpropanoic acids
Alternative Parents
Monocyclic monoterpenoids / Aromatic monoterpenoids / Phenylpropanes / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
2-phenylpropanoic-acid / P-cymene / Aromatic monoterpenoid / Monocyclic monoterpenoid / Monoterpenoid / Phenylpropane / Monocyclic benzene moiety / Benzenoid / Monocarboxylic acid or derivatives / Carboxylic acid
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid (CHEBI:5855)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51. [PubMed:12852704]
  2. Ouellet M, Falgueyret JP, Percival MD: Detergents profoundly affect inhibitor potencies against both cyclo-oxygenase isoforms. Biochem J. 2004 Feb 1;377(Pt 3):675-84. [PubMed:14510637]
  3. Gallego-Sandin S, Novalbos J, Rosado A, Gisbert JP, Galvez-Mugica MA, Garcia AG, Pajares JM, Abad-Santos F: Effect of ibuprofen on cyclooxygenase and nitric oxide synthase of gastric mucosa: correlation with endoscopic lesions and adverse reactions. Dig Dis Sci. 2004 Sep;49(9):1538-44. [PubMed:15481334]
  4. Murphey LJ, Williams MK, Sanchez SC, Byrne LM, Csiki I, Oates JA, Johnson DH, Morrow JD: Quantification of the major urinary metabolite of PGE2 by a liquid chromatographic/mass spectrometric assay: determination of cyclooxygenase-specific PGE2 synthesis in healthy humans and those with lung cancer. Anal Biochem. 2004 Nov 15;334(2):266-75. [PubMed:15494133]
  5. Sanchez-Fidalgo S, Martin-Lacave I, Illanes M, Motilva V: Angiogenesis, cell proliferation and apoptosis in gastric ulcer healing. Effect of a selective cox-2 inhibitor. Eur J Pharmacol. 2004 Nov 28;505(1-3):187-94. [PubMed:15556152]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51. [PubMed:12852704]
  2. Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. [PubMed:14592549]
  3. Gupta K, Kaub CJ, Carey KN, Casillas EG, Selinsky BS, Loll PJ: Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors. Bioorg Med Chem Lett. 2004 Feb 9;14(3):667-71. [PubMed:14741265]
  4. Martic M, Tatic I, Markovic S, Kujundzic N, Kostrun S: Synthesis, biological activity and molecular modeling studies of novel COX-1 inhibitors. Eur J Med Chem. 2004 Feb;39(2):141-51. [PubMed:14987823]
  5. Hillarp A: [Acetylsalicylic acid resistance--clinical diagnosis with unclear mechanism]. Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. [PubMed:15575422]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Yu L, Shi D, Ma L, Zhou Q, Zeng S: Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87. doi: 10.1002/bdd.1842. Epub 2013 Jun 3. [PubMed:23536207]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Modulator
General Function
Ubiquitin protein ligase binding
Specific Function
Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appea...
Gene Name
BCL2
Uniprot ID
P10415
Uniprot Name
Apoptosis regulator Bcl-2
Molecular Weight
26265.66 Da
References
  1. Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [PubMed:22668799]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Transmembrane signaling receptor activity
Specific Function
Thrombomodulin is a specific endothelial cell receptor that forms a 1:1 stoichiometric complex with thrombin. This complex is responsible for the conversion of protein C to the activated protein C ...
Gene Name
THBD
Uniprot ID
P07204
Uniprot Name
Thrombomodulin
Molecular Weight
60328.72 Da
References
  1. Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [PubMed:22668799]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Transporter activity
Specific Function
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds satu...
Gene Name
FABP2
Uniprot ID
P12104
Uniprot Name
Fatty acid-binding protein, intestinal
Molecular Weight
15207.165 Da
References
  1. Velkov T, Chuang S, Wielens J, Sakellaris H, Charman WN, Porter CJ, Scanlon MJ: The interaction of lipophilic drugs with intestinal fatty acid-binding protein. J Biol Chem. 2005 May 6;280(18):17769-76. Epub 2005 Feb 18. [PubMed:15722357]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Dill J, Patel AR, Yang XL, Bachoo R, Powell CM, Li S: A molecular mechanism for ibuprofen-mediated RhoA inhibition in neurons. J Neurosci. 2010 Jan 20;30(3):963-72. doi: 10.1523/JNEUROSCI.5045-09.2010. [PubMed:20089905]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Pdz domain binding
Specific Function
Involved in the transport of chloride ions. May regulate bicarbonate secretion and salvage in epithelial cells by regulating the SLC4A7 transporter. Can inhibit the chloride channel activity of ANO...
Gene Name
CFTR
Uniprot ID
P13569
Uniprot Name
Cystic fibrosis transmembrane conductance regulator
Molecular Weight
168139.895 Da
References
  1. Devor DC, Schultz BD: Ibuprofen inhibits cystic fibrosis transmembrane conductance regulator-mediated Cl- secretion. J Clin Invest. 1998 Aug 15;102(4):679-87. [PubMed:9710435]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA: Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1997 Feb 7;272(6):3406-10. [PubMed:9013583]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Thrombin receptor activity
Specific Function
GP-Ib, a surface membrane protein of platelets, participates in the formation of platelet plugs by binding to the A1 domain of vWF, which is already bound to the subendothelium.
Gene Name
GP1BA
Uniprot ID
P07359
Uniprot Name
Platelet glycoprotein Ib alpha chain
Molecular Weight
71539.265 Da
References
  1. Palayoor ST, J-Aryankalayil M, Makinde AY, Cerna D, Falduto MT, Magnuson SR, Coleman CN: Gene expression profile of coronary artery cells treated with nonsteroidal anti-inflammatory drugs reveals off-target effects. J Cardiovasc Pharmacol. 2012 Jun;59(6):487-99. doi: 10.1097/FJC.0b013e31824ba6b5. [PubMed:22668799]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
S100A7
Uniprot ID
P31151
Uniprot Name
Protein S100-A7
Molecular Weight
11470.87 Da
References
  1. Fujiwara R, Takenaka S, Hashimoto M, Narawa T, Itoh T: Expression of human solute carrier family transporters in skin: possible contributor to drug-induced skin disorders. Sci Rep. 2014 Jun 11;4:5251. doi: 10.1038/srep05251. [PubMed:24918694]

Enzymes

Details
1. Cytochrome P450 2C9
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Carlile DJ, Hakooz N, Bayliss MK, Houston JB: Microsomal prediction of in vivo clearance of CYP2C9 substrates in humans. Br J Clin Pharmacol. 1999 Jun;47(6):625-35. [PubMed:10383540]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  3. FDA label, Ibuprofen [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Yu L, Shi D, Ma L, Zhou Q, Zeng S: Influence of CYP2C8 polymorphisms on the hydroxylation metabolism of paclitaxel, repaglinide and ibuprofen enantiomers in vitro. Biopharm Drug Dispos. 2013 Jul;34(5):278-87. doi: 10.1002/bdd.1842. Epub 2013 Jun 3. [PubMed:23536207]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [PubMed:19949916]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
Gene Name
UGT2B4
Uniprot ID
P06133
Uniprot Name
UDP-glucuronosyltransferase 2B4
Molecular Weight
60512.035 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Not Available
Specific Function
Catalytic activity
Gene Name
AMACR
Uniprot ID
D6RB81
Uniprot Name
Alpha-methylacyl-CoA racemase
Molecular Weight
40674.37 Da
References
  1. Rainsford KD: Ibuprofen: pharmacology, efficacy and safety. Inflammopharmacology. 2009 Dec;17(6):275-342. doi: 10.1007/s10787-009-0016-x. Epub 2009 Nov 21. [PubMed:19949916]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Yamasaki K, Rahman MH, Tsutsumi Y, Maruyama T, Ahmed S, Kragh-Hansen U, Otagiri M: Circular dichroism simulation shows a site-II-to-site-I displacement of human serum albumin-bound diclofenac by ibuprofen. AAPS PharmSciTech. 2000 May 14;1(2):E12. [PubMed:14727845]
  2. Galantini L, Leggio C, Konarev PV, Pavel NV: Human serum albumin binding ibuprofen: a 3D description of the unfolding pathway in urea. Biophys Chem. 2010 Apr;147(3):111-22. doi: 10.1016/j.bpc.2010.01.002. Epub 2010 Jan 18. [PubMed:20117876]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [PubMed:15640378]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730]
  3. Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [PubMed:11099697]
  4. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [PubMed:11306713]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730]
  3. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [PubMed:15100168]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730]
  2. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [PubMed:10660625]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2018 10:08