| 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 |
|
| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- alpha-(4-Isobutylphenyl)propionate
- alpha-(4-Isobutylphenyl)propionic acid
- alpha-p-Isobutylphenylpropionate
- alpha-p-Isobutylphenylpropionic acid
- Duralbuprofen
- p-Isobutyl-2-phenylpropionate
- p-Isobutyl-2-phenylpropionic acid
- p-Isobutylhydratropate
- 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)
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| Substituents |
|
| Direct Parent |
Aromatic Monoterpenes |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
- Extracellular
- Membrane (predicted from logP)
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| 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) |
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| Predicted Properties |
|
| Spectra |
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| Biological Properties |
|---|
| Cellular Locations |
- Extracellular
- Membrane (predicted from logP)
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| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
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| 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
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| Pathways |
Not Available
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
242.0 (2.42-485.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|---|
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| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
1.528 +/- 0.563 uM |
Adult (>18 years old) |
Both |
nerve root compression pain |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.815 +/- 0.296 uM |
Adult (>18 years old) |
Both |
nerve root compression pain |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.000592 +/- 0.000170 uM |
Adult (>18 years old) |
Both |
thoracotomy for lobectomy |
Not Available |
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| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank 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  |
| KEGG Compound ID |
C01588 |
| BioCyc ID |
CARBOXYPHENYLAMINO-DEOXYRIBULOSE-P |
| BiGG ID |
Not Available |
| Wikipedia Link |
Ibuprofen |
| NuGOwiki Link |
HMDB01925 |
| Metagene Link |
HMDB01925 |
| METLIN ID |
572 |
| PubChem Compound |
3672 |
| PDB ID |
Not Available |
| ChEBI ID |
5855 |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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
- 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
- Al-Saidan SM: Transdermal self-permeation enhancement of ibuprofen. J Control Release. 2004 Nov 24;100(2):199-209.
Pubmed: 15544868
- Albert KS, Gernaat CM: Pharmacokinetics of ibuprofen. Am J Med. 1984 Jul 13;77(1A):40-6.
Pubmed: 6465162
- 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
- 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
- Horn AC, Jarrett SW: Ibuprofen-induced aseptic meningitis in rheumatoid arthritis. Ann Pharmacother. 1997 Sep;31(9):1009-11.
Pubmed: 9296242
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Salas-Herrera IG, Pearson RM, Turner P: Concentration of ibuprofen in cervical mucus. J Pharm Pharmacol. 1991 Feb;43(2):142-4.
Pubmed: 1672904
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