IBUPROFEN MEGLUMINE

Details

Stereochemistry	EPIMERIC
Molecular Formula	C13H18O2.C7H17NO5
Molecular Weight	401.4944
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CC(C)CC1=CC=C(C=C1)C(C)C(O)=O

InChI

InChIKey=VXVMMZWKWPUJIT-WZTVWXICSA-N

InChI=1S/C13H18O2.C7H17NO5/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15;1-8-2-4(10)6(12)7(13)5(11)3-9/h4-7,9-10H,8H2,1-3H3,(H,14,15);4-13H,2-3H2,1H3/t;4-,5+,6+,7+/m.0/s1

HIDE SMILES / InChI

Molecular Formula	C7H17NO5
Molecular Weight	195.2136
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C13H18O2
Molecular Weight	206.2808
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 8504

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 8583	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 1988
Common cold 58 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8583	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 1988
Muscular aches 12 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8583	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 1988
Backache 16 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8583	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 1988
Toothache 15 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608	Palliative	Approved 8583	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 1988

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 Health Status: unhealthy Age Group: 33 years Sex: M+F 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	unhealthy, 42 years (range: 17-73 years) Health Status: unhealthy Age Group: 42 years (range: 17-73 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf	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
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	unhealthy, 44 years (range: 20-69 years) Health Status: unhealthy Age Group: 44 years (range: 20-69 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf	Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (2 patients) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022348s000MedR.pdf
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: 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 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 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 Health Status: unhealthy 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 Health Status: unhealthy 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 Health Status: unhealthy 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 1946 inducer 1087	substrate 1193	substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 OAT3 747 OAT1 725 OAT2 153 OAT4 150 OCT1 620 MRP2 499 Nav1.7 32	CYP2C8 810 CYP2C19 1119 UGT1A3 470 UGT1A9 423 UGT2B4 278 UGT2B7 456 UGT2B17 237 UGT1A10 331 OATP1B1 503 OATP1B3 435 CYP1A2 1197 CYP2A6 626 CYP2E1 729 CYP4A11 137 UGT2B1 14

Drug as perpetrator

Target	Modality	Activity
MRP2 625	inhibitor 4027 Sources: https://www.jstage.jst.go.jp/article/dmpk/17/1/17_1_23/_article/-char/ja/ Page: 26.0	no
OAT3 749	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1111/cts.12486 Page: abstract	yes [IC50 4.4 uM]
CYP3A4 2633	inducer 1966 Sources: https://www.tandfonline.com/doi/abs/10.3109/00498254.2014.955831 Page: 8.0	yes
Nav1.7 32	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/abs/pii/S152659000400762X Page: abstract	yes
OAT1 730	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
OAT2 155	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
OAT4 150	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
OCT1 656	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
P-gp 1932	inhibitor 4027 Sources: https://www.tandfonline.com/doi/abs/10.3109/14756366.2016.1149476 Page: 867.0	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	minor
CYP2C19 1119	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	minor
CYP2C8 810	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	minor
CYP2A6 626	substrate 4014 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	no
CYP2E1 729	substrate 4014 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	no
CYP4A11 137	substrate 4014 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0006295297001433 Page: 37.0	no
OATP1B1 503	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	no
OATP1B3 435	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.tandfonline.com/doi/abs/10.1517/17425255.2012.680886 Page: 701.0	yes
CYP3A4 1946	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT1A10 331	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT1A3 470	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT1A9 423	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT2B1 14	substrate 4014 Sources: https://hrcak.srce.hr/index.php?show=clanak&id_clanak_jezik=227797 Page: 2.0	yes
UGT2B17 237	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT2B4 278	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes
UGT2B7 456	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4355401/ Page: 2.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 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
eMolecules	539665	https://www.emolecules.com/cgi-bin/more?vid=539665
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

PubMed

Title	Date	PubMed
Chemical reactivity in solid-state pharmaceuticals: formulation implications.	2001-05-16	11325479
Microencapsulation of ibuprofen and Eudragit RS 100 by the emulsion solvent diffusion technique.	2001-05-07	11337145
Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations.	2001-05-01	11318639
Invasive group A streptococcal infection and nonsteroidal antiinflammatory drug use among children with primary varicella.	2001-05	11331694
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001-05	11306713
Indomethacin and telomerase activity in tumor growth retardation.	2001-05	11295037
Pharmacokinetics of celecoxib in the presence and absence of interferon-induced acute inflammation in the rat: application of a novel HPLC assay.	2001-04-17	11302784
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.	2001-04-15	11309281
Inverse association of non-steroidal anti-inflammatory drugs and malignant melanoma among women.	2001-04-11	11295097
IL-10 mediation of activation-induced TH1 cell apoptosis and lymphoid dysfunction in polymicrobial sepsis.	2001-04-07	11298491
Use of glucosamine and chondroitin sulfate in the management of osteoarthritis.	2001-04-03	11281631
[Misuse of drugs in recreational sports].	2001-04	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.	2001-04	11341362
Obsessive-compulsive disorder: a neuronal membrane phospholipid hypothesis and concomitant therapeutic strategy.	2001-04	11339839
Group B Streptococci and inducible nitric oxide synthase: modulation by nuclear factor kappa B and ibuprofen.	2001-04	11339667
Ibuprofen-lysine for closure of patent ductus arteriosus.	2001-04	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.	2001-04	11331497
Ibuprofen-induced bullous leukocytoclastic vasculitis.	2001-04	11324392
Celecoxib and rofecoxib. The role of COX-2 inhibitors in dental practice.	2001-04	11315375
Induced accumulation of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) in maize leaves.	2001-04	11314951
Renal failure and vestibular toxicity in an adolescent with cystic fibrosis receiving gentamicin and standard-dose ibuprofen.	2001-04	11288217
Nonsurgical female sterilization: comparison of intrauterine application of quinacrine alone or in combination with ibuprofen.	2001-04	11287047
Percutaneous, intramuscular neuromuscular electrical stimulation for the treatment of shoulder subluxation and pain in chronic hemiplegia: a case report.	2001-04	11277137
The effect of standard care, ibuprofen, and music on pain relief and patient satisfaction in adults with musculoskeletal trauma.	2001-04	11275859
Esophageal laceration and charcoal mediastinum complicating gastric lavage.	2001-04	11267816
Permeability of endothelial monolayers to albumin is increased by bradykinin and inhibited by prostaglandins.	2001-04	11238014
Linear drug eruption.	2001-03-29	11275808
Coexisting linear and disseminated drug eruption: a clinical clue to the understanding of the genetic basis of drug eruptions.	2001-03-29	11275799
Investigation of foreign substances in food.	2001-03-29	11272336
Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water.	2001-03-16	11293584
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.	2001-03-15	11266649
NSAIDs bound to methacrylic carriers: microstructural characterization and in vitro release analysis.	2001-03-12	11245914
[Necrotizing fasciitis. Clinical criteria and risk factors].	2001-03	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.	2001-03	11291760
Synthesis and hydrolytic behaviour of glycerol-1,2-diibuprofenate-3-nitrate, a putative pro-drug of ibuprofen and glycerol-1-nitrate.	2001-03	11291749
Inhibitors of arachidonic acid metabolism have variable effects on calcium signaling pathways.	2001-03	11281236
Pharmacokinetics, safety, and tolerability of BAY 12-9566 and nonsteroidal anti-inflammatory agents (naproxen, ibuprofen) during coadministration in patients with osteoarthritis.	2001-03	11269574
Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals.	2001-03	11259508
Association of human herpesvirus 6 infection with drug reaction with eosinophilia and systemic symptoms.	2001-03	11255328
Audit of pain management at home following tonsillectomy in children.	2001-03	11244527
Seeking a simple measure of analgesia for mega-trials: is a single global assessment good enough?	2001-03	11240091
Continuous low-level topical heat in the treatment of dysmenorrhea.	2001-03	11239634
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.	2001-02-23	11263577
Investigational COX-2 inhibitor relieves pain in dental model.	2001-02	11320990
Determination of nonsteroidal anti-inflammatory drugs in biological fluids by automatic on-line integration of solid-phase extraction and capillary electrophoresis.	2001-02	11258759
Activity profile of glycolamide ester prodrugs of ibuprofen.	2001-01	11247537
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

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:58:35 GMT 2025` Edited by `admin` on `Mon Mar 31 22:58:35 GMT 2025`
Record UNII	56SFW97YYQ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

IBUPROFEN MEGLUMINE

Common Name

English

ARTRENE

Preferred Name

English

Ibuprofen meglumine [WHO-DD]

Common Name

English

(2R,3R,4R,5S)-6-(METHYLAMINO)HEXANE-1,2,3,4,5-PENTOL, 2-(4-(2-METHYLPROPYL)PHENYL)PROPANOIC ACID

Systematic Name

English

IBUPROFEN METHYLGLUCAMINE SALT

Common Name

English

BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, COMPD. WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:1)

Systematic Name

English

D-GLUCITOL, 1-DEOXY-1-(METHYLAMINO)-, .ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETATE (SALT)

Systematic Name

English

D-GLUCITOL, 1-DEOXY-1-(METHYLAMINO)-, .ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETATE (1:1)

Systematic Name

English

2-(4-ISOBUTYLPHENYL)PROPANOIC ACID-1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:1)

Systematic Name

English

Code System Code Type Description

PUBCHEM

9930909