IBUPROFEN

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H18O2
Molecular Weight	206.2808
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CC1=CC=C(C=C1)C(C)C(O)=O

InChI

InChIKey=HEFNNWSXXWATRW-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20718179

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. It’s used temporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps and temporarily reduces fever. 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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15481334	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Headache 47 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8429	IBU-TAB Approved Use temporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date 5.8717438E11
Common cold 58 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8429	IBU-TAB Approved Use temporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date 5.8717438E11
Muscular aches 12 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8429	IBU-TAB Approved Use temporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date 5.8717438E11
Backache 16 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8429	IBU-TAB Approved Use temporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date 5.8717438E11
Toothache 15 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8429	IBU-TAB Approved Use temporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date 5.8717438E11

C_max

Value	Dose	Co-administered	Analyte	Population
27.9 μg/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/6465162	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		IBUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
103 μg × h/mL REVIEW https://www.ncbi.nlm.nih.gov/pubmed/6465162	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		IBUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.2 h REVIEW https://www.ncbi.nlm.nih.gov/pubmed/6465162	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		IBUPROFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% REVIEW https://onlinelibrary.wiley.com/doi/10.1002/9781118743614.ch4			IBUPROFEN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
199800 mg single, oral Overdose Dose: 199800 mg Route: oral Route: single Dose: 199800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18072160	unknown, 17 years Health Status: unknown Age Group: 17 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18072160	Other AEs: Cardiovascular collapse, Acidosis... Other AEs: Cardiovascular collapse (grade 5, 1 patient) Acidosis (grade 5, 1 patient) Hypothermia (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18072160
90 g single, oral Overdose Dose: 90 g Route: oral Route: single Dose: 90 g Sources: https://pubmed.ncbi.nlm.nih.gov/20419362	unknown, 19 years Health Status: unknown Age Group: 19 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20419362	Other AEs: Polyuria, Acidosis... Other AEs: Polyuria (1 patient) Acidosis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/20419362
800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21127424	unhealthy, 33 years n = 40 Health Status: unhealthy Age Group: 33 years Sex: M+F Population Size: 40 Sources: https://pubmed.ncbi.nlm.nih.gov/21127424	Other AEs: Acute respiratory distress syndrome, Tachypnea... Other AEs: Acute respiratory distress syndrome (serious, 1 patient) Tachypnea (serious, 1 patient) Septic shock (serious, 1 patient) Breathlessness (serious, 1 patient) Septicemia (serious, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/21127424
400 mg 4 times / day multiple, intravenous Recommended Dose: 400 mg, 4 times / day Route: intravenous Route: multiple Dose: 400 mg, 4 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf Page: p.87	unhealthy, 42 years (range: 17-73 years) n = 195 Health Status: unhealthy Age Group: 42 years (range: 17-73 years) Sex: M+F Population Size: 195 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf Page: p.87	Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (2%) Headache (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf Page: p.87
800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf Page: p.87	unhealthy, 44 years (range: 20-69 years) n = 304 Health Status: unhealthy Age Group: 44 years (range: 20-69 years) Sex: M+F Population Size: 304 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf Page: p.87	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (2 patients) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf Page: p.87
240000 mg single, oral Overdose Dose: 240000 mg Route: oral Route: single Dose: 240000 mg Co-administed with:: divalproex sodium Sources: https://pubmed.ncbi.nlm.nih.gov/18072160	unknown, 49 years Health Status: unknown Age Group: 49 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/18072160	Other AEs: Cardiovascular collapse... Other AEs: Cardiovascular collapse (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18072160
240000 mg single, oral Overdose Dose: 240000 mg Route: oral Route: single Dose: 240000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/18072160	unknown, 49 years Health Status: unknown Age Group: 49 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/18072160	Other AEs: Acidosis, Hypothermia... Other AEs: Acidosis (grade 5, 1 patient) Hypothermia (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18072160
400 mg 4 times / day multiple, intravenous Recommended Dose: 400 mg, 4 times / day Route: intravenous Route: multiple Dose: 400 mg, 4 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022348lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: Pain Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022348lbl.pdf	Other AEs: Myocardial infarction, Stroke... Other AEs: Myocardial infarction (serious\|grade 5) Stroke (serious\|grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022348lbl.pdf
400 mg 6 times / day multiple, oral Recommended Dose: 400 mg, 6 times / day Route: oral Route: multiple Dose: 400 mg, 6 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/017463s105lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: pain Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/017463s105lbl.pdf	Other AEs: Myocardial infarction, Stroke... Other AEs: Myocardial infarction (serious\|grade 5) Stroke (serious\|grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/017463s105lbl.pdf
200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: https://clinicaltrials.gov/ct2/show/NCT01842633	unhealthy n = 62 Health Status: unhealthy Condition: Episodic Tension Type Headache Population Size: 62 Sources: https://clinicaltrials.gov/ct2/show/NCT01842633	Other AEs: Depression, Insomnia... Other AEs: Depression (below serious, 1 patient) Insomnia (below serious, 1 patient) Oropharyngeal pain (below serious, 1 patient) Sinus congestion (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT01842633
97.5 mg 4 times / day multiple, oral Dose: 97.5 mg, 4 times / day Route: oral Route: multiple Dose: 97.5 mg, 4 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01420653	unhealthy n = 112 Health Status: unhealthy Condition: Dental Pain Population Size: 112 Sources: https://clinicaltrials.gov/ct2/show/NCT01420653	Other AEs: Facial swelling... Other AEs: Facial swelling (below serious, 8 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01420653
10 mg/kg single, oral Dose: 10 mg/kg Route: oral Route: single Dose: 10 mg/kg Sources: https://clinicaltrials.gov/ct2/show/NCT02241512	unhealthy n = 29 Health Status: unhealthy Condition: Post-ERCP Pancreatitis Population Size: 29 Sources: https://clinicaltrials.gov/ct2/show/NCT02241512	Other AEs: Bleeding, Perforation... Other AEs: Bleeding (below serious, 2 patients) Perforation (below serious, 1 patient) Sources: https://clinicaltrials.gov/ct2/show/NCT02241512

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inducer 781	substrate 1037	substrate 1217	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 OAT3 642 OAT1 599 OAT2 145 OAT4 146 OCT1 512 MRP2 383 Nav1.7 36	CYP2C8 693 CYP2C19 991 UGT1A3 422 UGT1A9 380 UGT2B4 249 UGT2B7 389 UGT2B17 213 UGT1A10 291 OATP1B1 406 OATP1B3 350 CYP1A2 1054 CYP2A6 543 CYP2E1 667 CYP4A11 119 UGT2B1 14

Drug as perpetrator

Target	Modality	Activity
MRP2 475	inhibitor 3277 Sources: https://www.jstage.jst.go.jp/article/dmpk/17/1/17_1_23/_article/-char/ja/ Page: 26.0	no
OAT3 644	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1111/cts.12486 Page: abstract	yes [IC50 4.4 uM]
CYP3A4 1925	inducer 1573 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2014.955831 Page: 8.0	yes
Nav1.7 36	inhibitor 3277 Sources: https://www.sciencedirect.com/science/article/abs/pii/S152659000400762X Page: abstract	yes
OAT1 603	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
OAT2 147	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
OAT4 146	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
OCT1 543	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
P-gp 1650	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.3109/14756366.2016.1149476 Page: 867.0	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	minor
CYP2C19 991	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	minor
CYP2C8 693	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	minor
CYP2A6 543	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	no
CYP2D6 1217	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	no
CYP2E1 667	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	no
CYP4A11 119	substrate 3367 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	no
OATP1B1 406	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	no
OATP1B3 350	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	no
CYP2C9 1037	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1517/17425255.2012.680886 Page: 701.0	yes
CYP3A4 1737	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT1A10 291	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT1A3 422	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT1A9 380	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT2B1 14	substrate 3367 Sources: https://hrcak.srce.hr/index.php?show=clanak&id_clanak_jezik=227797 Page: 2.0	yes
UGT2B17 213	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT2B4 249	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT2B7 389	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.frontiersin.org/articles/10.3389/fphar.2012.00003/full Page: 5.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5855	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5855
ChemicalBook	CB3699656	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3699656
ChemicalBook	CB4336930	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4336930
ChemicalBook	CB92675917	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB92675917
MolPort	MolPort-001-791-802	https://www.molport.com/shop/molecule-link/MolPort-001-791-802
Selleck Chemicals	Ibuprofen(Advil)	http://www.selleckchem.com/products/Ibuprofen(Advil).html
eMolecules	539665	https://www.emolecules.com/cgi-bin/more?vid=539665

PubMed

Title	Date	PubMed
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries.	2001	11296921
Non-steroidal anti-inflammatory drugs protect against chondrocyte apoptotic death.	2001	11296547
Interpolymer complexation. II. Entrapment of ibuprofen by in-situ complexation between polyvinyl acetate phthalate (PVAP) and polyvinylpyrrolidone (PVP) and development of a chewable tablet formulation.	2001	11247277
A benefit/risk analysis of the prevention of brain ischaemia with anticoagulant drugs: when, how and whom to treat?	2001	11244207
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations.	2001	11228592
[Misuse of drugs in recreational sports].	2001 Apr	11344954
Reversible binding of the novel anti-tumour agent 5,6-dimethylxanthenone-4-acetic acid to plasma proteins and its distribution into blood cells in various species.	2001 Apr	11341362
Obsessive-compulsive disorder: a neuronal membrane phospholipid hypothesis and concomitant therapeutic strategy.	2001 Apr	11339839
Group B Streptococci and inducible nitric oxide synthase: modulation by nuclear factor kappa B and ibuprofen.	2001 Apr	11339667
Ibuprofen-lysine for closure of patent ductus arteriosus.	2001 Apr	11332944
In vitro effect of different non-steroidal anti-inflammatory drugs on human polymorphonuclear leukocyte activity measured by luminol-dependent chemiluminescence of the whole blood.	2001 Apr	11331497
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice.	2001 Apr	11315375
Induced accumulation of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) in maize leaves.	2001 Apr	11314951
Renal failure and vestibular toxicity in an adolescent with cystic fibrosis receiving gentamicin and standard-dose ibuprofen.	2001 Apr	11288217
Nonsurgical female sterilization: comparison of intrauterine application of quinacrine alone or in combination with ibuprofen.	2001 Apr	11287047
Percutaneous, intramuscular neuromuscular electrical stimulation for the treatment of shoulder subluxation and pain in chronic hemiplegia: a case report.	2001 Apr	11277137
Esophageal laceration and charcoal mediastinum complicating gastric lavage.	2001 Apr	11267816
Permeability of endothelial monolayers to albumin is increased by bradykinin and inhibited by prostaglandins.	2001 Apr	11238014
Nitric oxide-releasing nonsteroidal anti-inflammatory drugs (NSAIDs) alter the kinetics of human colon cancer cell lines more effectively than traditional NSAIDs: implications for colon cancer chemoprevention.	2001 Apr 15	11309281
IL-10 mediation of activation-induced TH1 cell apoptosis and lymphoid dysfunction in polymicrobial sepsis.	2001 Apr 7	11298491
Investigational COX-2 inhibitor relieves pain in dental model.	2001 Feb	11320990
Determination of nonsteroidal anti-inflammatory drugs in biological fluids by automatic on-line integration of solid-phase extraction and capillary electrophoresis.	2001 Feb	11258759
The use of anti-inflammatory drugs in cancer pain.	2001 Feb	11237777
Ibuprofen affects pro- and anti-inflammatory cytokine production by mononuclear cells of preterm newborns.	2001 Feb	11223651
[Topical administration is better than oral administration].	2001 Feb 1	11234523
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.	2001 Feb 23	11263577
Ibuprofen versus indomethacin for closure of patent ductus arteriosus.	2001 Feb 8	11221607
Activity profile of glycolamide ester prodrugs of ibuprofen.	2001 Jan	11247537
Effect of a single dose of ibuprofen lysinate before embryo transfer on pregnancy rates in cows.	2001 Jan	11226038
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg.	2001 Jan 10	11231885
Pharmacokinetics of celecoxib in the presence and absence of interferon-induced acute inflammation in the rat: application of a novel HPLC assay.	2001 Jan-Apr	11302784
Investigation of foreign substances in food.	2001 Jan-Feb	11272336
Allergic reactions due to ibuprofen in children.	2001 Jan-Feb	11207978
[Necrotizing fasciitis. Clinical criteria and risk factors].	2001 Mar	11319368
Synthesis of N-pyridinyl(methyl)-1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carboxamides and analogues and their anti-inflammatory activity in mice and rats.	2001 Mar	11291760
Synthesis and hydrolytic behaviour of glycerol-1,2-diibuprofenate-3-nitrate, a putative pro-drug of ibuprofen and glycerol-1-nitrate.	2001 Mar	11291749
Inhibitors of arachidonic acid metabolism have variable effects on calcium signaling pathways.	2001 Mar	11281236
Pharmacokinetics, safety, and tolerability of BAY 12-9566 and nonsteroidal anti-inflammatory agents (naproxen, ibuprofen) during coadministration in patients with osteoarthritis.	2001 Mar	11269574
Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals.	2001 Mar	11259508
Continuous low-level topical heat in the treatment of dysmenorrhea.	2001 Mar	11239634
Agonist-specific regulation of monocyte chemoattractant protein-1 expression by cyclooxygenase metabolites in hepatic stellate cells.	2001 Mar	11230753
Analysis of nonsteroidal antiinflammatory drugs in meconium and its relation to persistent pulmonary hypertension of the newborn.	2001 Mar	11230592
Expression of rat liver long-chain acyl-CoA synthetase and characterization of its role in the metabolism of R-ibuprofen and other fatty acid-like xenobiotics.	2001 Mar 15	11266649
Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water.	2001 Mar 16	11293584
Linear drug eruption.	2001 Mar-Apr	11275808
Coexisting linear and disseminated drug eruption: a clinical clue to the understanding of the genetic basis of drug eruptions.	2001 Mar-Apr	11275799
Invasive group A streptococcal infection and nonsteroidal antiinflammatory drug use among children with primary varicella.	2001 May	11331694
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Chemical reactivity in solid-state pharmaceuticals: formulation implications.	2001 May 16	11325479
Microencapsulation of ibuprofen and Eudragit RS 100 by the emulsion solvent diffusion technique.	2001 May 7	11337145

Patents

Sample Use Guides

In Vivo Use Guide

adults: take 1 tablet every 4 to 6 hours while symptoms persist. If pain or fever does not respond to 1 tablet, 2 tablets may be used; do not exceed 6 tablets in 24 hours. Children under 12 years: ask a doctor.

Route of Administration: Oral

In Vitro Use Guide

Ibuprofen, in a 400-μM concentration, decreased the expression of Hsp70 by 23% in comparison with untreated cells, whereas other NSAID had no effect. Ibuprofen also decreased the expression of Hsp70 in H358, a human lung adenocarcinoma cell line, in a dose-dependent manner (from 0-400 uM).

Name

Type

Language

IBUPROFEN

Official Name

English

IBUPROFEN COMPONENT OF ADVIL ALLERGY SINUS

Common Name

English

IB-100

Code

English

IBUPROFEN COMPONENT OF SINE-AID IB

Common Name

English

IBUPROFEN COMPONENT OF CHILDREN'S MOTRIN COLD

Common Name

English

ibuprofen [INN]

Common Name

English

U-18,573

Code

English

COMBOGESIC COMPONENT IBUPROFEN

Brand Name

English

IBUPROFEN COMPONENT OF VICOPROFEN

Common Name

English

PROFEN

Brand Name

English

IBUPROFEN [EP MONOGRAPH]

Common Name

English

(±)-2-(P-ISOBUTYLPHENYL)PROPIONIC ACID

Common Name

English

CAP-PROFEN

Brand Name

English

IBUPROFEN COMPONENT OF COMBOGESIC

Brand Name

English

IBUPROFEN [MI]

Common Name

English

IBUPROFEN [ORANGE BOOK]

Common Name

English

IBUPROFEN COMPONENT OF REPREXAIN

Common Name

English

IBUPROFEN [EMA EPAR]

Common Name

English

(±)-P-ISOBUTYLHYDRATROPIC ACID

Common Name

English

TAB-PROFEN

Brand Name

English

VICOPROFEN COMPONENT IBUPROFEN

Common Name

English

IBUPROFEN [HSDB]

Common Name

English

IBUPROFEN [USP-RS]

Common Name

English

NSC-256857

Code

English

BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL), (±)-

Common Name

English

ADVIL ALLERGY SINUS COMPONENT IBUPROFEN

Common Name

English

IBUPROFEN [INCI]

Common Name

English

IBU-TAB

Brand Name

English

CALDOLOR

Brand Name

English

BURANA

Brand Name

English

IBUPROFEN [MART.]

Common Name

English

NUPRIN

Brand Name

English

ADVIL CONGESTION RELIEF COMPONENT IBUPROFEN

Common Name

English

ACHES-N-PAIN

Brand Name

English

IBUPROFEN COMPONENT OF COMBUNOX

Common Name

English

IBUPROFEN [USP MONOGRAPH]

Common Name

English

MIDOL

Brand Name

English

IBUPROFEN COMPONENT OF CHILDREN'S ADVIL COLD

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-

Common Name

English

M01AE01

Code

English

(±)-IBUPROFEN

Common Name

English

CHILDREN'S ADVIL COLD COMPONENT IBUPROFEN

Common Name

English

IBUPROFEN COMPONENT OF ADVIL CONGESTION RELIEF

Common Name

English

U-18573

Code

English

COMBUNOX COMPONENT IBUPROFEN

Common Name

English

REPREXAIN COMPONENT IBUPROFEN

Common Name

English

RD 13621

Code

English

IBUPRIN

Brand Name

English

MEDIPREN

Brand Name

English

RUFEN

Brand Name

English

Ibuprofen [WHO-DD]

Common Name

English

PEDEA

Brand Name

English

IBUPROFEN [USAN]

Common Name

English

IBUPROFEN [WHO-IP]

Common Name

English

IBUPROFEN [VANDF]

Common Name

English

MOTRIN

Brand Name

English

IBU

Brand Name

English

SINE-AID IB COMPONENT IBUPROFEN

Common Name

English

IBUPROFENUM [WHO-IP LATIN]

Common Name

English

IBUPROFEN [JAN]

Common Name

English

CHILDREN'S MOTRIN COLD COMPONENT IBUPROFEN

Common Name

English

IBUPROFEN [USP IMPURITY]

Common Name

English

IBUPROHM

Brand Name

English

ADVIL

Brand Name

English

Classification Tree Code System Code

WHO-ATC

N02AJ19