Ibuprofen

IBUPROFEN
Identification
Name Ibuprofen
Accession Number DB01050 (APRD00372)
Type small molecule
Groups Approved
Ibuprofen, a propionic acid derivative, is a prototypical nonsteroidal anti-

Description
inflammatory agent (NSAIA) with analgesic and antipyretic properties.
Structure
Download: MOL | SDF | SMILES | InChI

Display: 2D Structure | 3D Structure
Ibuprophen
Synonyms P-Isobutylhydratropic Acid
Para-Isobutylhydratropic Acid
Salts Not Available
Name Company
Act-3
Actiprofen
Adex
Adran
Advil
Brand names Advil Liqui-Gels
Aktren
Alaxan
Alges-X
Algoflex
Brand Name Ingredients

Brand mixtures
Advil Cold & Sinus ibuprofen + pseudoephedrine HCl
Brand Name Ingredients
Advil Cold & Sinus
ibuprofen + pseudoephedrine HCl
Daytime
Advil Cold and Sinus ibuprofen + pseudoephedrine HCll +
Nighttime chlorpheniramine maleate
Advil Cold and Sinus ibuprofen + pseudoephedrine HCl +
Plus chlorpheniramine maleate
Advil Flu & Body Ache ibuprofen + pseudoephedrine HCl
Children's Advil Cold ibuprofen + pseudoephedrine HCl
Dristan Sinus Caplets ibuprofen + pseudoephedrine HCl
Motrin Children's Cold ibuprofen + pseudoephedrine HCl
Motrin Sinus Headache ibuprofen + pseudoephedrine HCl
Robax Platinum methocarbamol + ibuprofen
Anti-inflammatory Agents
Cyclooxygenase Inhibitors
Analgesics
Categories
Analgesics, Non-Narcotic
Antipyretics
Nonsteroidal Anti-inflammatory Agents (NSAIAs)
CAS number 15687-27-1

Average: 206.2808
Weight
Monoisotopic: 206.13067982
Chemical Formula C13H18O2
InChI Key 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-
InChI 10H,8H2,1-3H3,(H,14,15)
Plain Text
IUPAC Name 2-[4-(2-methylpropyl)phenyl]propanoic acid
SMILES CC(C)CC1=CC=C(C=C1)C(C)C(O)=O
Plain Text
Mass Spec show (11.4 KB)
Taxonomy
Kingdom Organic
Classes Phenylacetates
Hydroxy Compounds
Acetates
Carboxylic Acids and Derivatives

Substructures
Phenylacetates
Benzene and Derivatives
Aromatic compounds
Pharmacology
For symptomatic treatment of rheumatoid arthritis, juvenile rheumatoid
arthritis and osteoarthritis. May be used to treat mild to moderate pain and
for the management of dysmenorrhea. May be used to reduce fever. Has been
used with some success for treating ankylosing spondylitis, gout and
Indication
psoriatic arthritis. May reduce pain, fever and inflammation of pericarditis.
May be used IV with opiates to relieve moderate to severe pain. Ibuprofen
lysine may be used IV to treat patent ductus arteriosus (PDA) in premature
neonates.
Ibuprofen is a nonsteroidal anti-inflammatory agent (NSAIA) or nonsteroidal
anti-inflammatory drug (NSAID), with analgesic and antipyretic properties.
Pharmacodynamic
Ibuprofen has pharmacologic actions similar to those of other prototypical
s
NSAIAs, which are thought to act through inhibition of prostaglandin
synthesis.
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,
Mechanism of fever and swelling. Antipyretic effects may be due to action on the
action hypothalamus, resulting in an increased peripheral blood flow, vasodilation,
and subsequent heat dissipation. Inhibition of COX-1 is thought to cause
some of the side effects of ibuprofen including GI ulceration. Ibuprofen is
administered as a racemic mixture. The R-enantiomer undergoes extensive
interconversion to the S-enantiomer in vivo. The S-enantiomer is believed to
be the more pharmacologically active enantiomer.
Absorption ~ 80% absorbed from GI tract
Time to reach peak plasma concentration = 47 minutes (suspension), 62
minutes (chewable tablets), 120 minutes (conventional tablets)
Volume of
Not Available
distribution
90-99% to whole human plasma and site II of purified albumin, binding
Protein binding appears to be saturable and becomes non-linear at concentrations exceeding
20 mcg/ml.
R-enanatiomer undergoes extensive enantiomeric conversion (53-65%) to the
more active S-enantiomer in vivo. Metablized by oxidation to 2 inactive
metabolites: (+)-2[4-(2-hydroxy-2-methylpropyl)phenyl]propionic acid and
(+)-2-[4-(2-carboxypropyl)phenyl]propionic acid. Very small amounts of 1-
hydroxyibuprofen and 3-hydroxyibuprofen have been recovered from urine.
Cytochrome P450 2C9 is the major catalyst in the formation of oxidative
metabolites. Oxidative metabolites may be conjugated to glucuronide prior to
excretion.
Important The metabolism module of DrugBank is currently in beta.

Questions or suggestions? Please contact us.
Substrate Enzymes Product
UDP-
glucuronosyltransf
erase 1-1
Metabolism UDP-
glucuronosyltransf
erase 1-3
UDP-
Ibuprofen glucuronosyltransf Ibuprofen glucuronide Details
erase 1-9
UDP-
glucuronosyltransf
erase 2B4
UDP-
glucuronosyltransf
erase 2B7
Ibuprofen 2-Hydroxyibuprofen Details

Cytochrome P450
2C8
Cytochrome P450
2C9
Cytochrome P450
2C8
Ibuprofen 3-Hydroxyibuprofen Details
Cytochrome P450
2C9
(+)-2-[4'-(2-
Ibuprofen carboxypropyl)phenyl]propioni Details
c acid
(+)-2[4'-(2-hydroxy-2-
Ibuprofen methylpropyl)phenyl]propionic Details
acid
Ibuprofen 1-hydroxyibuprofen Details
Ibuprofen Carboxy-ibuprofen Details
Route of
Ibuprofen is rapidly metabolized and eliminated in the urine.
elimination
Half life 2-4 hours
Clearance Not Available
Side effects: May cause peripheral edema and fluid retention. Use caution in
patients with congestive heart failure or severe uncontrolled hypertension.
May cause dyspepsia, heartburn, nausea, vomiting, anorexia, diarrhea,
constipation, stomatitis, flatulence, bloating, epigastric pain, and abdominal
pain. Peptic ulcer and GI bleeding have been reported. May also cause
dizziness, headache and nervousness. Acute renal failure accompanied by
acute tubular necrosis has been reported.
Toxicity Most common symptoms of overdose are abdominal pain, nausea, vomiting,
lethargy, vertigo, drowsiness (somnolence), dizziness and insomnia. Other
symptoms of overdose include headache, loss of consciousness, tinnitus,
CNS depression, convulsions and seizures. May rarely cause metabolic
acidosis, abnormal hepatic function, hyperkalemia, renal failure, dyspnea,
respiratory depression, coma, acute renal failure, and apnea (primarily in
very young pediatric patients).
LD50=1255mg/kg(orally in mice)
Affected
Humans and other mammals
organisms
Pathway Name SMPDB ID
Pathways
Ibuprofen Pathway SMP00086
Pharmacoeconomics
Manufacturers
Wyeth consumer healthcare
Banner pharmacaps inc
Contract pharmacal corp
Dr reddys laboratories ltd
Marksans pharma ltd
Bayer healthcare llc
Cumberland pharmaceuticals inc
Mcneil consumer healthcare
Perrigo co
Tris pharma inc
Mcneil consumer products co div mcneilab inc
Alterna tchp llc
L perrigo co
Abbott laboratories pharmaceutical products div

Actavis mid atlantic llc
Perrigo r and d co
Mcneil consumer healthcare div mcneil ppc inc
Mcneil pediatrics
Lederle laboratories div american cyanamid co
Basf corp
Pliva inc
Advent pharmaceuticals inc
Amneal pharmaceuticals ny llc
Dr reddys laboratories louisiana llc
Dr reddys laboratories inc
Halsey drug co inc
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Leiner health products inc
Lnk international inc
Mutual pharmaceutical co inc
Mylan pharmaceuticals inc
Mylan laboratories inc
Northstar healthcare holdings ltd
Ohm corp
Ohm laboratories inc

Par pharmaceutical inc
Purepac pharmaceutical co
Sandoz inc
Shasun usa inc
Superpharm corp
Teva pharmaceuticals usa inc
Vintage pharmaceuticals inc
Watson laboratories inc
Alra laboratories inc
Bristol myers products inc
Lundbeck inc
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 Form Route Strength

Capsule Oral 200 mg
Concentrate Intravenous 100 mg/ml
Suspension Oral 100 mg/5 ml
Form Route Strength
Suspension Oral 40 mg/ml
Tablet Oral 200 mg
Tablet Oral 400 mg
Tablet Oral 600 mg
Tablet Oral 800 mg
Tablet, chewable Oral 100 mg
Tablet, chewable Oral 50 mg
Unit description Cost Unit

Neoprofen 20 mg/2 ml vial 304.5 USD ml
Caldolor 400 mg/4 ml vial 2.21 USD ml
Caldolor 800 mg/8 ml vial 1.58 USD ml
Nuprin arthritis patch 1.11 USD patch
Ibuprofen powder 1.04 USD g
Nuprin muscle & joint patch 1.03 USD patch
Prices Profen II 45-800 mg 12 Hour tablet 0.69 USD tablet
Motrin 800 mg tablet 0.59 USD tablet
Advil allergy sinus caplet 0.5 USD caplet
Ibu-drops 40 mg/ml suspension drops 0.42 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for
informational purposes only.
Country Patent Number Approved Expires (estimated)
Patents United States 6727286 2001-11-27 2021-11-27
United States 5215755 1993-06-01 2010-06-01
Properties
State Solid
Property Value Source
melting point 76 C PhysProp
YALKOWSKY,SH &
water solubility 21 mg/L (at 25 C)
DANNENFELSER,RM (1992)
Experimental
logP 3.97 AVDEEF,A (1997)
Properties
logS -3.99 ADME Research, USCD
Caco2
-4.28 ADME Research, USCD
permeability
pKa 4.91 SANGSTER (1994)
Predicted Property Value Source
Properties water solubility 6.84e-02 g/l ALOGPS
logP 3.5 ALOGPS
logP 3.84 ChemAxon
logS -3.5 ALOGPS
pKa (strongest acidic) 4.85 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor
2 ChemAxon
count
hydrogen donor count 1 ChemAxon
polar surface area 37.3 ChemAxon
rotatable bond count 4 ChemAxon
Refractivity 60.73 ChemAxon
Polarizability 23.76 ChemAxon
References
Synthesis
http://en.wikipedia.org/wiki/Ibuprofen#Synthesis
Reference
1. Zawada ET Jr: Renal consequences of nonsteroidal antiinflammatory

drugs. Postgrad Med. 1982 May;71(5):223-30. Pubmed
2. Townsend KP, Pratico D: Novel therapeutic opportunities for

Alzheimers disease: focus on nonsteroidal anti-inflammatory drugs.
FASEB J. 2005 Oct;19(12):1592-601. Pubmed
3. Chen H, Jacobs E, Schwarzschild MA, McCullough ML, Calle EE,

Thun MJ, Ascherio A: Nonsteroidal antiinflammatory drug use and
the risk for Parkinsons disease. Ann Neurol. 2005 Dec;58(6):963-7.
Pubmed
General Reference 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
5. Bergner T, Przybilla B: Photosensitization caused by ibuprofen. J Am

Acad Dermatol. 1992 Jan;26(1):114-6. Pubmed
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
External Links Resource Link

KEGG Drug D00126
KEGG Compound C01588
PubChem Compound 3672
PubChem Substance 46507255
ChemSpider 3544
ChEBI 5855
ChEMBL 5855
Therapeutic Targets Database DAP000780
PharmGKB PA449957
IUPHAR 2713
Guide to Pharmacology 2713
HET IBP
Drug Product Database 636525
RxList http://www.rxlist.com/cgi/generic/ibup.htm
Drugs.com http://www.drugs.com/ibuprofen.html
Wikipedia http://en.wikipedia.org/wiki/Ibuprofen
C01EB16
G02CC01
ATC Codes M01AE01
M01AE14
M02AA13
AHFS Codes 28:08.04.92
PDB Entries Not Available

FDA label show (1.77 MB)
MSDS show (73.5 KB)
Interactions
Drug Interactions Drug Interaction
Acebutolol Risk of inhibition of renal prostaglandins
The NSAID, ibuprofen, may increase the anticoagulant
Acenocoumarol
effect of acenocoumarol.
Acetylsalicylic acid Concomitant therapy of the NSAID, ketoprofen, and
acetylsalicylic acid may result in additive adverse/toxic
effects (e.g. GI bleeding). The NSAID may also limit
the cardioprotective effect of acetylsalicylic acid.
Occasional concomitant use may not cause clinically
significant problems, but regular, frequent concomitant
therapy is not recommended.
Alendronate Increased risk of gastric toxicity
Anisindione
effect of anisindione.
Atenolol Risk of inhibition of renal prostaglandins
Increases toxicity of each. May deteriorate renal
Azilsartan
function, particularly in volume depleted or elderly
medoxomil
patients. Decreases effects of azilsartan by antagonism.
Nonsteroidal Anti-Inflammatory Agents such as
ibuprofen may diminish the antihypertensive effect of
Beta-Blockers such as betaxolol. Monitor for increases
in blood pressure if a nonsteroidal anti-inflammatory
Betaxolol agent (NSAID) is initiated/dose increased, or decreases
in blood pressure if a NSAID is discontinued/dose
decreased; this is particularly important if NSAID
treatment is for extended periods of time. Ophthalmic
beta-blockers are likely of little concern.
Bevantolol Risk of inhibition of renal prostaglandins
Bisoprolol Risk of inhibition of renal prostaglandins
The NSAID, ibuprofen, may antagonize the diuretic and
Bumetanide antihypertensive effects of the loop diuretic,
bumetanide.
Carteolol Risk of inhibition of renal prostaglandins
Carvedilol Risk of inhibition of renal prostaglandins
Bile acid sequestrants may decrease the absorption of
Nonsteroidal Anti-Inflammatory Agents. Monitor for
decreased serum concentrations/therapeutic effects of
nonsteroidal anti-inflammatory agents (NSAID) if
coadministered with bile acid sequestrants. Separating
Colesevelam
the administration of doses by 2 or more hours may
reduce (but not eliminate) the risk of interaction. The
manufacturer of colesevelam recommends that drugs
should be administered at least 1 hour before or 4 hours
after colesevelam.
Cyclosporine Monitor for nephrotoxicity
Dicumarol
effect of dicumarol.
Increases levels of Ibuprofen via metabolism decrease.
Eltrombopag UDP-glucuronosyltransferase inhibition with unclear
significance.
Esmolol Risk of inhibition of renal prostaglandins
Ethacrynic acid antihypertensive effects of the loop diuretic, ethacrynic
acid.
Furosemide
antihypertensive effects of the loop diuretic, furosemide.
Additive anticoagulant/antiplatelet effects may increase
Ginkgo biloba
bleed risk. Concomitant therapy should be avoided.
Avoid combination with ibuprofen and other
nonsteroidal anti-inflammatory drugs (NSAIDs) due to
the potential enhancement of homoharringtonine
Homoharringtonine
associated bleeding-related adverse effects. Specifically
it is suggested to avoid this combination in patients with
a platelet count of less than 50,000/uL.
Labetalol Risk of inhibition of renal prostaglandins
The NSAID, ibuprofen, may decrease the renal
Lithium
excretion of lithium. Increased risk of lithium toxicity.
The NSAID, ibuprofen, may decrease the renal
Methotrexate excretion of methotrexate. Increased risk of
methotrexate toxicity.
Metoprolol Risk of inhibition of renal prostaglandins
Nadolol Risk of inhibition of renal prostaglandins
Oxprenolol Risk of inhibition of renal prostaglandins
Penbutolol Risk of inhibition of renal prostaglandins
Pindolol Risk of inhibition of renal prostaglandins
Practolol Risk of inhibition of renal prostaglandins
NSAIDs increase the risk of toxicity due to impairment
of renal clearance of pralatrexate thus increasing
Pralatrexate
exposure. Monitor for adverse effects or adjust dose of
pralatrexate.
Coadministration with NSAIDS used chronically may
Prasugrel
increase the risk of bleeding.
Propranolol Risk of inhibition of renal prostaglandins
Sotalol Risk of inhibition of renal prostaglandins
Ibuprofen may reduce clearance rate of Tamoxifen.
Monitor for changes in therapeutic/adverse effects of
Tamoxifen
Tamoxifen if Ibuprofen is initiated, discontinued or dose
changed.
Ibuprofen, a strong CYP2C9 inhibitor, may decrease the
metabolism and clearance of Tolbutamide, a CYP2C9
Tolbutamide substrate. Consider alternate therapy or monitor for
changes in Tolbutamide therapeutic and adverse effects
if Ibuprofen is initiated, discontinued or dose changed.
The NSAID, ibuprofen, may decrease the diuretic and
Torasemide
antihypertensive effect of the loop diuretic, torasemide.
Trandolapril The NSAID, Ibuprofen, may reduce the antihypertensive
effect of Trandolapril. Consider alternate therapy or
monitor for changes in Trandolapril efficacy if
Ibuprofen is initiated, discontinued or dose changed.
The prostacyclin analogue, Treprostinil, may increase
the risk of bleeding when combined with the NSAID,
Treprostinil
Ibuprofen. Monitor for increased bleeding during
concomitant thearpy.
The metabolite of triflusal, 2-hydroxy-4-trifluoro-
methyl-benzoic acid (HTB), impairs the serum protein
binding of ibuprofen to the same extent as acetylsalisylic
Triflusal
acid. Thus, the free fraction of glisentide may be
increased. A dosage reduction may be required if used in
combination.
The strong CYP2C9 inhibitor, Ibuprofen, may decrease
the metabolism and clearance of Trimethoprim, a
CYP2C9 substrate. Consider alternate therapy or
Trimethoprim
monitor for changes in therapeutic and adverse effects of
Trimethoprim if Ibuprofen is initiated, discontinued or
dose changed.
Increased risk of bleeding with concomitant use of non-
Vilazodone
steroidal anti-inflammatory drugs with vilazodone.
Ibuprofen, a strong CYP2C9 inhibitor, may increase the
serum concentration of voriconazole by decreasing its
Voriconazole metabolism. Monitor for changes in the therapeutic and
adverse effects of voriconazole if ibuprofen is initiated,
discontinued or dose changed.
Ibuprofen, a strong CYP2C9 inhibitor, may decrease the
metabolism of warfarin. The antiplatelet effect of
ibuprofen may also increase the bleed risk associated
Warfarin with warfarin. Consider alternate therapy or monitor for
changes in the therapeutic and adverse effects of
warfarin if ibuprofen is initiated, discontinued or dose
changed.
Avoid alcohol
Food delays the time to reach peak plasma concentrations by 30-60

Food Interactions minutes and reduces peak plasma concentrations by 30-50%. Extent
of absorption is unaffected.
Take with food to reduce gastric irritation.
Targets
1. Prostaglandin G/H synthase 2
Pharmacological action: yes

Actions: inhibitor
May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in
activity-dependent plasticity
Organism class: human

UniProt ID: P35354
Gene: PTGS2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
1. Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51.
Pubmed
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
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
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
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
6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002
Jan 1;30(1):412-5. Pubmed
Pharmacological action: yes
May play an important role in regulating or promoting cell proliferation in some normal and
neoplastically transformed cells

UniProt ID: P23219
Gene: PTGS1
SNPs: SNPJam Report
References:
1. Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51.
Pubmed
2. Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease.

Thromb Res. 2003 Jun 15;110(5-6):281-6. Pubmed
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
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
5. Hillarp A: [Acetylsalicylic acid resistanceclinical diagnosis with unclear mechanism]

Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. Pubmed
6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002
Jan 1;30(1):412-5. Pubmed
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

3. Pubmed

3. Pubmed

3. Pubmed

3. Pubmed

3. Pubmed

3. Pubmed

3. Pubmed

3. Pubmed

3. Pubmed

3. Pubmed
3. Apoptosis regulator Bcl-2
Pharmacological action: unknown

Actions: modulator
Suppresses apoptosis in a variety of cell systems including factor-dependent

lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial
membrane permeability. Appears to function in a feedback loop system with caspases. Inhibits
caspase activity either by preventing the release of cytochrome c from the mitochondria and/or
by binding to the apoptosis-activating factor (APAF-1)

UniProt ID: P10415
Gene: BCL2
SNPs: SNPJam Report
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
4. Thrombomodulin

Actions: modulator
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 (protein Ca). Once evolved, protein Ca scissions the activated cofactors of the
coagulation mechanism, factor Va and factor VIIIa, and thereby reduces the amount of thrombin
generated

UniProt ID: P07204
Gene: THBD
SNPs: SNPJam Report
References:
5. Tissue-type plasminogen activator

Actions: negative modulator
Converts the abundant, but inactive, zymogen plasminogen to plasmin by hydrolyzing a single
Arg-Val bond in plasminogen. By controlling plasmin-mediated proteolysis, it plays an
important role in tissue remodeling and degradation, in cell migration and many other
physiopathological events. Play a direct role in facilitating neuronal migration

UniProt ID: P00750
Gene: PLAT
SNPs: SNPJam Report
References:
6. Fatty acid-binding protein, intestinal

Actions: binder
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
saturated long-chain fatty acids with a high affinity, but binds with a lower affinity to
unsaturated long- chain fatty acids. FABP2 may also help maintain energy homeostasis by
functioning as a lipid sensor
UniProt ID: P12104
Gene: FABP2
SNPs: SNPJam Report
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
7. Peroxisome proliferator-activated receptor gamma

Actions: activator
Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once
activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase
and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of
fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis

UniProt ID: P37231
Gene: PPARG
SNPs: SNPJam Report
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
8. Cystic fibrosis transmembrane conductance regulator

Actions: inhibitor
Involved in the transport of chloride ions. May regulate bicarbonate secretion and salvage in
epithelial cells by regulating the SLC4A7 transporter

UniProt ID: P13569
Gene: CFTR
SNPs: SNPJam Report
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
Enzymes
1. Cytochrome P450 2C9
Actions: substrate, inhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme
contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-
warfarin, diclofenac, phenytoin, tolbutamide and losartan
UniProt ID: P11712

Gene: CYP2C9
SNPs: SNPJam Report
References:
1. Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features
and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009
Dec;10(10):1075-126. Pubmed
2. 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
3. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana
University School of Medicine (2007). Accessed May 28, 2010.
4. 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. Epub 2009 Nov 24. Pubmed
5. 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
Actions: substrate
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the
epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids.
It is the principal enzyme responsible for the metabolism the anticancer drug paclitaxel (taxol)
UniProt ID: P10632

Gene: CYP2C8
SNPs: SNPJam Report
References:


3. Pubmed

Actions: substrate
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 imipramine
UniProt ID: P33261

Gene: CYP2C19
SNPs: SNPJam Report
References:

4. UDP-glucuronosyltransferase 1-1
Actions: substrate
UDPGT is of major importance in the conjugation and subsequent elimination of potentially

toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX- alpha
to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate
UniProt ID: P22309

Gene: UGT1A1
SNPs: SNPJam Report
References:
Actions: substrate
toxic xenobiotics and endogenous compounds
UniProt ID: P35503

Gene: UGT1A3
SNPs: SNPJam Report
References:
Actions: substrate

toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols
UniProt ID: O60656

Gene: UGT1A9
SNPs: SNPJam Report
References:
7. UDP-glucuronosyltransferase 2B4
Actions: substrate
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 estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-
methylumbelliferone, 1-naphthol, 4- nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and
menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid
UniProt ID: P06133

Gene: UGT2B4
SNPs: SNPJam Report
References:
8. UDP-glucuronosyltransferase 2B7
Actions: substrate
Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important
role in regulating the level and activity of these potent and active estrogen metabolites
UniProt ID: P16662

Gene: UGT2B7
SNPs: SNPJam Report
References:
Actions: inhibitor
May play an important role in regulating or promoting cell proliferation in some normal and
neoplastically transformed cells
UniProt ID: P23219

Gene: PTGS1
SNPs: SNPJam Report
References:
Actions: inhibitor
May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in
activity-dependent plasticity
UniProt ID: P35354

Gene: PTGS2
SNPs: SNPJam Report
References:
Transporters
1. Solute carrier organic anion transporter family member 2B1
Actions: substrate
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the

prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
UniProt ID: O94956

Gene: SLCO2B1
SNPs: SNPJam Report
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
2. Multidrug resistance protein 1
Actions: substrate
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-

resistant cells
UniProt ID: P08183

Gene: ABCB1
SNPs: SNPJam Report
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
3. Multidrug resistance-associated protein 4
Actions: inhibitor
May be an organic anion pump relevant to cellular detoxification
UniProt ID: O15439

Gene: ABCC4
SNPs: SNPJam Report
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
4. Multidrug resistance-associated protein 1
Actions: inhibitor
May participate directly in the active transport of drugs into subcellular organelles or influence
drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May
protect milk against xenobiotics
UniProt ID: P33527

Gene: ABCC1
SNPs: SNPJam Report
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
5. Solute carrier organic anion transporter family member 1A2
Actions: inhibitor
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP)

and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity)
UniProt ID: P46721

Gene: SLCO1A2
SNPs: SNPJam Report
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
6. Solute carrier family 22 member 6
Actions: inhibitor
UniProt ID: Q4U2R8
Gene: hROAT1
SNPs: SNPJam Report
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
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
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
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
Actions: inhibitor
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,
fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD),
2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and
ochratoxin (OTA)
UniProt ID: Q8TCC7

Gene: SLC22A8
SNPs: SNPJam Report
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

Pubmed
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
Actions: inhibitor
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related

compounds
UniProt ID: Q9NSA0

Gene: SLC22A11
SNPs: SNPJam Report
References:

Pubmed
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
Carriers
1. Serum albumin
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
colloidal osmotic pressure of blood
UniProt ID: P02768

Gene: ALB
SNPs: SNPJam Report
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

Ibuprofen

Caricato da

Informazioni sul documento

Copyright

Formati disponibili

Condividi questo documento

Condividi o incorpora il documento

Opzioni di condivisione

Hai trovato utile questo documento?

Questo contenuto è inappropriato?

Copyright:

Formati disponibili

Ibuprofen

Caricato da

Copyright:

Formati disponibili

IBUPROFEN

Ibuprofen, a propionic acid derivative, is a prototypical nonsteroidal anti-

Download: MOL | SDF | SMILES | InChI

Brand Name Ingredients

Nonsteroidal Anti-inflammatory Agents (NSAIAs)

CAS number 15687-27-1

Carboxylic Acids and Derivatives

Benzene and Derivatives

Important The metabolism module of DrugBank is currently in beta.

Substrate Enzymes Product

Ibuprofen 2-Hydroxyibuprofen Details

Pathway Name SMPDB ID

Banner pharmacaps inc

Contract pharmacal corp

Dr reddys laboratories ltd

Marksans pharma ltd

Bayer healthcare llc

Cumberland pharmaceuticals inc

Mcneil consumer healthcare

Tris pharma inc

Mcneil consumer products co div mcneilab inc

Alterna tchp llc

Abbott laboratories pharmaceutical products div

Mcneil consumer healthcare div mcneil ppc inc

Lederle laboratories div american cyanamid co

Advent pharmaceuticals inc

Amneal pharmaceuticals ny llc

Dr reddys laboratories louisiana llc

Dr reddys laboratories inc

Halsey drug co inc

Ivax pharmaceuticals inc sub teva pharmaceuticals usa

Leiner health products inc

Lnk international inc

Mutual pharmaceutical co inc

Mylan pharmaceuticals inc

Mylan laboratories inc

Northstar healthcare holdings ltd

Ohm laboratories inc

Shasun usa inc

Teva pharmaceuticals usa inc

Vintage pharmaceuticals inc

Watson laboratories inc

Alra laboratories inc

Bristol myers products inc

Advanced Pharmaceutical Services Inc.

Aidarex Pharmacuticals LLC

Altura Pharmaceuticals Inc.

Amerisource Health Services Corp.

Apothecary Shop Wholesale

Ascend Laboratories LLC

Atlantic Biologicals Corporation

Ben Venue Laboratories Inc.

Bryant Ranch Prepack

Central Texas Community Health Centers

Coupler Enterprises Inc.

Darby Dental Supply Co. Inc.

Dept Health Central Pharmacy

Direct Dispensing Inc.

Diversified Healthcare Services Inc.

Doctor Reddys Laboratories Ltd.

Golden State Medical Supply Inc.

Group Health Cooperative

H.J. Harkins Co. Inc.

Heartland Repack Services LLC