Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C13H18O2 |
Molecular Weight | 206.2808 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CC1=CC=C(C=C1)[C@H](C)C(O)=O
InChI
InChIKey=HEFNNWSXXWATRW-JTQLQIEISA-N
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)/t10-/m0/s1
Dexibuprofen, S(+)-ibuprofen, is a non-steroidal anti-inflammatory drug and active dextrorotatory enantiomer of ibuprofen. Pharmacotherapeutic effects of dexibuprofen are more potent with lesser side effects than that of the racemic mixture of both isomers. In the acute and chronic treatment of osteoarthritis, it exhibits equivalent efficacy and tolerability as that of celecoxib. Dexibuprofen is a non-selective inhibitor of cyclooxygenase (COX), which is an enzyme involved in prostaglandin (mediators of pain and fever) and thromboxane (stimulators of blood clotting) synthesis via the arachidonic acid pathway. Dexibuprofen is a non-selective cyclooxygenase inhibitor and hence, it inhibits the activity of both COX-1 and COX-2. The inhibition of COX-2 activity decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever, and swelling while the inhibition of COX-1 is thought to cause some of the side effects of Dexibuprofen including GI ulceration. The major disadvantage of dexibuprofen is its low bioavailability, the account of its low solubility in physiological media.
Approval Year
PubMed
Title | Date | PubMed |
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Effectiveness evaluation of available without prescription medicines for postoperative pain treatment after "one day surgery". | 2001 Jul-Sep |
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Efficacy and long-term safety of dexibuprofen [S(+)-ibuprofen]: a short-term efficacy study in patients with osteoarthritis of the hip and a 1-year tolerability study in patients with rheumatic disorders. | 2001 Nov |
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Treatment of non-malignant pain in the Dutch GP population: an analysis of treatment standards, prescription habits and basic attitudes. | 2001 Nov |
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Ibuprofen interference in the determination of 3-phenoxybenzoic acid in urine. | 2001 Nov |
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Aseptic meningo-encephalitis related to dexibuprofen use in a patient with systemic lupus erythematosus: a case report with MR findings. | 2002 |
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Stereoselectivity of ibuprofen metabolism and pharmacokinetics following the administration of the racemate to healthy volunteers. | 2002 Aug |
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Enantioselective release of controlled delivery granules based on molecularly imprinted polymers. | 2002 Jan-Mar |
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Enantiospecific effects of cytochrome P450 2C9 amino acid variants on ibuprofen pharmacokinetics and on the inhibition of cyclooxygenases 1 and 2. | 2002 Jul |
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The cyclooxygenase inhibitor ibuprofen and the FLAP inhibitor MK886 inhibit pancreatic carcinogenesis induced in hamsters by transplacental exposure to ethanol and the tobacco carcinogen NNK. | 2002 Oct |
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Dexibuprofen: pharmacology, therapeutic uses and safety. | 2003 |
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Influence of age on the enantiomeric disposition of ibuprofen in healthy volunteers. | 2003 Jun |
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Synthesis and evaluation of S-4-(3-thienyl)phenyl-alpha-methylacetic acid. | 2004 Feb 23 |
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Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins. | 2005 |
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A supported liquid membrane encapsulating a surfactant-lipase complex for the selective separation of organic acids. | 2005 Feb 4 |
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The interaction of lipophilic drugs with intestinal fatty acid-binding protein. | 2005 May 6 |
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An eutomer/distomer ratio near unity does not justify non-enantiospecific assay methods in bioequivalence studies. | 2005 Oct |
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Similarity in structures of racemic and enantiomeric ibuprofen sodium dihydrates. | 2005 Sep |
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[Study on ion beam mutagenizing of the Trichosporon lactis T for enantioselective separation of ibuprofen]. | 2006 Apr |
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Evidence of COX-2 independent induction of apoptosis and cell cycle block in human colon carcinoma cells after S- or R-ibuprofen treatment. | 2006 Jul 1 |
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Dynamic kinetic resolution: alternative approach in optimizing S-ibuprofen production. | 2006 Mar |
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Binding studies of taxanes to human serum albumin by bioaffinity chromatography and circular dichroism. | 2006 Sep 11 |
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A novel method for assessing inhibition of ibuprofen chiral inversion and its application in drug discovery. | 2007 Apr 20 |
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A review of ibuprofen and acetaminophen use in febrile children and the occurrence of asthma-related symptoms. | 2007 Dec |
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Further characterization of a rat model of varicella zoster virus-associated pain: Relationship between mechanical hypersensitivity and anxiety-related behavior, and the influence of analgesic drugs. | 2007 Feb 23 |
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Effect of absorption rate on pharmacokinetics of ibuprofen in relation to chiral inversion in humans. | 2007 Nov |
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Free drug metabolic clearance in elderly people. | 2008 |
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S-ibuprofen effectively inhibits thromboxane B2 levels and platelet function in an experimental model of lipopolysaccharide-stimulated and non-stimulated whole blood. | 2008 |
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Development of an affinity silica monolith containing human serum albumin for chiral separations. | 2008 Apr 14 |
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Formulation of a extended release tablet containing dexibuprofen. | 2008 Dec |
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The effects and safety of dexibuprofen compared with ibuprofen in febrile children caused by upper respiratory tract infection. | 2008 Dec |
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Population pharmacokinetic analysis of Ibuprofen enantiomers in preterm newborn infants. | 2008 Dec |
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Analgesic synergy between topical opioids and topical non-steroidal anti-inflammatory drugs in the mouse model of thermal pain. | 2008 Jan 28 |
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Dexibuprofen (S(+)-isomer ibuprofen) reduces microglial activation and impairments of spatial working memory induced by chronic lipopolysaccharide infusion. | 2008 May |
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Impaired intrinsic chiral inversion activity of ibuprofen in rats with adjuvant-induced arthritis. | 2008 Nov |
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Influence of benzylamine on the resolution of ibuprofen with (+)-(R)-phenylethylamine via supercritical fluid extraction. | 2009 Jun |
Patents
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M01AE14
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QM01AE14
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C166907
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SUB07030MIG
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100000083204
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51146-56-6
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JJ-29
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DEXIBUPROFEN
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43415
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39912
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C539402
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759814
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DTXSID9048724
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CHEMBL175
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DB09213
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671DKG7P5S
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6426
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ACTIVE MOIETY
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