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Record Information
Version3.6
Creation Date2006-05-18 08:36:36 UTC
Update Date2014-09-23 05:28:23 UTC
HMDB IDHMDB01925
Secondary Accession Numbers
  • HMDB01872
Metabolite Identification
Common NameIbuprofen
DescriptionIbuprofen is a nonsteroidal anti-inflammatory drug (NSAID) widely marketed under various trademarks including Act-3, Advil, Brufen, Motrin, Nuprin, and Nurofen. It is used for relief of symptoms of arthritis, primary dysmenorrhoea, and fever; Ibuprofen is an NSAID which is believed to work through inhibition of cyclooxygenase (COX), thus inhibiting prostaglandin synthesis. There are at least 2 variations of cyclooxygenase (COX-1 and COX-2), ibuprofen inhibits both COX-1 and COX-2. It appears that its analgesic, antipyretic, and anti-inflammatory activity are achieved principally through COX-2 inhibition; whereas COX-1 inhibition is responsible for its unwanted effects on platelet aggregation and the GI mucosa. As with other NSAIDs, ibuprofen inhibits platelet aggregation, but is not used therapeutically for this action since it is a minor and reversible effect. -- Wikipedia.
Structure
Thumb
Synonyms
  1. alpha-(4-Isobutylphenyl)propionate
  2. alpha-(4-Isobutylphenyl)propionic acid
  3. alpha-p-Isobutylphenylpropionate
  4. alpha-p-Isobutylphenylpropionic acid
  5. Duralbuprofen
  6. p-Isobutyl-2-phenylpropionate
  7. p-Isobutyl-2-phenylpropionic acid
  8. p-Isobutylhydratropate
  9. p-Isobutylhydratropic acid
Chemical FormulaC13H18O2
Average Molecular Weight206.2808
Monoisotopic Molecular Weight206.13067982
IUPAC Name2-[4-(2-methylpropyl)phenyl]propanoic acid
Traditional Name(+-)-ibuprofen
CAS Registry Number15687-27-1
SMILES
CC(C)CC1=CC=C(C=C1)C(C)C(O)=O
InChI Identifier
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)
InChI KeyHEFNNWSXXWATRW-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassPrenol Lipids
Sub ClassMonoterpenes
Other Descriptors
  • Monocyclic Monoterpenes
  • Organic Compounds
  • Phenylacetic Acid Derivatives
  • monocarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct ParentAromatic Monoterpenes
Ontology
StatusDetected and Quantified
Origin
  • Drug
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point76 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.021 mg/mL at 25 °CNot Available
LogP3.97AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP3.5ALOGPS
logP3.84ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)4.85ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity60.73ChemAxon
Polarizability23.79ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Stratum Corneum
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified242.0 (2.42-485.0) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified1.528 +/- 0.563 uMAdult (>18 years old)Bothnerve root compression pain details
Cerebrospinal Fluid (CSF)Detected and Quantified0.815 +/- 0.296 uMAdult (>18 years old)Bothnerve root compression pain details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000592 +/- 0.000170 uMAdult (>18 years old)BothBronchial carcinoma details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022743
KNApSAcK IDNot Available
Chemspider ID3544
KEGG Compound IDC01588
BioCyc IDCARBOXYPHENYLAMINO-DEOXYRIBULOSE-P
BiGG IDNot Available
Wikipedia LinkIbuprofen
NuGOwiki LinkHMDB01925
Metagene LinkHMDB01925
METLIN ID572
PubChem Compound3672
PDB IDNot Available
ChEBI ID5855
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Perioli L, Ambrogi V, Angelici F, Ricci M, Giovagnoli S, Capuccella M, Rossi C: Development of mucoadhesive patches for buccal administration of ibuprofen. J Control Release. 2004 Sep 14;99(1):73-82. Pubmed: 15342182
  2. Whitlam JB, Brown KF, Crooks MJ, Room GF: Transsynovial distribution of ibuprofen in arthritic patients. Clin Pharmacol Ther. 1981 Apr;29(4):487-92. Pubmed: 7471614
  3. Al-Saidan SM: Transdermal self-permeation enhancement of ibuprofen. J Control Release. 2004 Nov 24;100(2):199-209. Pubmed: 15544868
  4. Albert KS, Gernaat CM: Pharmacokinetics of ibuprofen. Am J Med. 1984 Jul 13;77(1A):40-6. Pubmed: 6465162
  5. Alam I, Ferrell LD, Bass NM: Vanishing bile duct syndrome temporally associated with ibuprofen use. Am J Gastroenterol. 1996 Aug;91(8):1626-30. Pubmed: 8759674
  6. Townsend RJ, Benedetti TJ, Erickson SH, Cengiz C, Gillespie WR, Gschwend J, Albert KS: Excretion of ibuprofen into breast milk. Am J Obstet Gynecol. 1984 May 15;149(2):184-6. Pubmed: 6720796
  7. Horn AC, Jarrett SW: Ibuprofen-induced aseptic meningitis in rheumatoid arthritis. Ann Pharmacother. 1997 Sep;31(9):1009-11. Pubmed: 9296242
  8. Van Overmeire B, Allegaert K, Casaer A, Debauche C, Decaluwe W, Jespers A, Weyler J, Harrewijn I, Langhendries JP: Prophylactic ibuprofen in premature infants: a multicentre, randomised, double-blind, placebo-controlled trial. Lancet. 2004 Nov 27-Dec 3;364(9449):1945-9. Pubmed: 15567010
  9. Castillo M, Smith PC: Disposition and reactivity of ibuprofen and ibufenac acyl glucuronides in vivo in the rhesus monkey and in vitro with human serum albumin. Drug Metab Dispos. 1995 May;23(5):566-72. Pubmed: 7587932
  10. Hockertz S, Heckenberger R, Emmendorffer A, Muller M: Influence of ibuprofen on the infection with Listeria monocytogenes. Arzneimittelforschung. 1995 Jan;45(1):104-7. Pubmed: 7893261
  11. Day RO, Williams KM, Graham GG, Lee EJ, Knihinicki RD, Champion GD: Stereoselective disposition of ibuprofen enantiomers in synovial fluid. Clin Pharmacol Ther. 1988 May;43(5):480-7. Pubmed: 3365913
  12. Trappe TA, White F, Lambert CP, Cesar D, Hellerstein M, Evans WJ: Effect of ibuprofen and acetaminophen on postexercise muscle protein synthesis. Am J Physiol Endocrinol Metab. 2002 Mar;282(3):E551-6. Pubmed: 11832356
  13. Laffi G, Daskalopoulos G, Kronborg I, Hsueh W, Gentilini P, Zipser RD: Effects of sulindac and ibuprofen in patients with cirrhosis and ascites. An explanation for the renal-sparing effect of sulindac. Gastroenterology. 1986 Jan;90(1):182-7. Pubmed: 3079594
  14. Goldenberg NA, Jacobson L, Manco-Johnson MJ: Brief communication: duration of platelet dysfunction after a 7-day course of Ibuprofen. Ann Intern Med. 2005 Apr 5;142(7):506-9. Pubmed: 15809462
  15. Yao M, Zhou W, Sangha S, Albert A, Chang AJ, Liu TC, Wolfe MM: Effects of nonselective cyclooxygenase inhibition with low-dose ibuprofen on tumor growth, angiogenesis, metastasis, and survival in a mouse model of colorectal cancer. Clin Cancer Res. 2005 Feb 15;11(4):1618-28. Pubmed: 15746067
  16. Jabor VA, Lanchote VL, Bonato PS: Enantioselective analysis of ibuprofen in human plasma by anionic cyclodextrin-modified electrokinetic chromatography. Electrophoresis. 2002 Sep;23(17):3041-7. Pubmed: 12207314
  17. Salas-Herrera IG, Pearson RM, Turner P: Concentration of ibuprofen in cervical mucus. J Pharm Pharmacol. 1991 Feb;43(2):142-4. Pubmed: 1672904

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
General function:
Involved in monooxygenase 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 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.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in transport
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:
ALB
Uniprot ID:
P02768
Molecular weight:
69365.9