Human Metabolome Database Version 3.5

Showing metabocard for Ibuprofen (HMDB01925)

Record Information
Version 3.5
Creation Date 2006-05-18 02:36:36 -0600
Update Date 2013-02-08 17:11:01 -0700
HMDB ID HMDB01925
Secondary Accession Numbers
  • HMDB01872
Metabolite Identification
Common Name Ibuprofen
Description Ibuprofen 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C13H18O2
Average Molecular Weight 206.2808
Monoisotopic Molecular Weight 206.13067982
IUPAC Name 2-[4-(2-methylpropyl)phenyl]propanoic acid
Traditional IUPAC Name (+-)-ibuprofen
CAS Registry Number 15687-27-1
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 Key HEFNNWSXXWATRW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Monoterpenes
Other Descriptors
  • Monocyclic Monoterpenes
  • Organic Compounds
  • Phenylacetic Acid Derivatives
  • monocarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct Parent Aromatic Monoterpenes
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 76 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.021 mg/mL at 25 °C Not Available
LogP 3.97 AVDEEF,A (1997)
Predicted Properties
Property Value Source
Water Solubility 0.068 g/L ALOGPS
LogP 3.50 ALOGPS
LogP 3.84 ChemAxon
LogS -3.48 ALOGPS
pKa (strongest acidic) 4.85 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 60.73 ChemAxon
Polarizability 23.79 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum EI-B (HITACHI RMU-6E)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Testes
  • Kidney
  • Epidermis
  • Myelin
  • Prostate
  • Adrenal Gland
  • Adipose Tissue
  • Adrenal Cortex
  • Nerve Cells
  • Platelet
  • Spleen
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
242.0 (2.42-485.0) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 1.528 +/- 0.563 uM Adult (>18 years old) Both nerve root compression pain
Cerebrospinal Fluid (CSF) Detected and Quantified 0.815 +/- 0.296 uM Adult (>18 years old) Both nerve root compression pain
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000592 +/- 0.000170 uM Adult (>18 years old) Both thoracotomy for lobectomy
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022743
KNApSAcK ID Not Available
Chemspider ID 3544 Link_out
KEGG Compound ID C01588 Link_out
BioCyc ID CARBOXYPHENYLAMINO-DEOXYRIBULOSE-P Link_out
BiGG ID Not Available
Wikipedia Link Ibuprofen Link_out
NuGOwiki Link HMDB01925 Link_out
Metagene Link HMDB01925 Link_out
METLIN ID 572 Link_out
PubChem Compound 3672 Link_out
PDB ID Not Available
ChEBI ID 5855 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  3. Al-Saidan SM: Transdermal self-permeation enhancement of ibuprofen. J Control Release. 2004 Nov 24;100(2):199-209. Pubmed: 15544868 Link_out
  4. Albert KS, Gernaat CM: Pharmacokinetics of ibuprofen. Am J Med. 1984 Jul 13;77(1A):40-6. Pubmed: 6465162 Link_out
  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 Link_out
  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 Link_out
  7. Horn AC, Jarrett SW: Ibuprofen-induced aseptic meningitis in rheumatoid arthritis. Ann Pharmacother. 1997 Sep;31(9):1009-11. Pubmed: 9296242 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Amine oxidase [flavin-containing] B
Reactions: Not Available
Gene Name: MAOB
Uniprot ID: P27338 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C1
Reactions: Not Available
Gene Name: AKR1C1
Uniprot ID: Q04828 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldo-keto reductase family 1 member C2
Reactions: Not Available
Gene Name: AKR1C2
Uniprot ID: P52895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 2
Reactions: Not Available
Gene Name: PTGS2
Uniprot ID: P35354 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 1
Reactions: Not Available
Gene Name: PTGS1
Uniprot ID: P23219 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum albumin
Reactions: Not Available
Gene Name: ALB
Uniprot ID: P02768 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA