Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H18O2.C6H14N2O2.H2O |
| Molecular Weight | 370.4837 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.NCCCC[C@H](N)C(O)=O.CC(C)CC1=CC=C(C=C1)[C@H](C)C(O)=O
InChI
InChIKey=ZLGIZCLYTDPXEP-LQDNOSPQSA-N
InChI=1S/C13H18O2.C6H14N2O2.H2O/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15;7-4-2-1-3-5(8)6(9)10;/h4-7,9-10H,8H2,1-3H3,(H,14,15);5H,1-4,7-8H2,(H,9,10);1H2/t10-;5-;/m00./s1
| Molecular Formula | C13H18O2 |
| Molecular Weight | 206.2808 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C6H14N2O2 |
| Molecular Weight | 146.1876 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Influence of benzylamine on the resolution of ibuprofen with (+)-(R)-phenylethylamine via supercritical fluid extraction. | 2009-06 |
|
| Cyclic resolution of racemic ibuprofen via coupled efficient lipase and acid-base catalysis. | 2009-03 |
|
| ADIDAC trial: analgesia with dexibuprofen versus ibuprofen in patients suffering from primary dysmenorrhea: a crossover trial. | 2009 |
|
| Formulation of a extended release tablet containing dexibuprofen. | 2008-12 |
|
| The effects and safety of dexibuprofen compared with ibuprofen in febrile children caused by upper respiratory tract infection. | 2008-12 |
|
| Population pharmacokinetic analysis of Ibuprofen enantiomers in preterm newborn infants. | 2008-12 |
|
| Impaired intrinsic chiral inversion activity of ibuprofen in rats with adjuvant-induced arthritis. | 2008-11 |
|
| Characterization of drug-protein binding process by employing equilibrium sampling through hollow-fiber supported liquid membrane and Bjerrum and Scatchard plots. | 2008-09-10 |
|
| Enantioselective formation of ibuprofen-S-acyl-glutathione in vitro in incubations of ibuprofen with rat hepatocytes. | 2008-09 |
|
| Spinal nerve ligation-induced activation of nuclear factor kappaB is facilitated by prostaglandins in the affected spinal cord and is a critical step in the development of mechanical allodynia. | 2008-08-26 |
|
| Influence of CYP2C8 and CYP2C9 polymorphisms on pharmacokinetic and pharmacodynamic parameters of racemic and enantiomeric forms of ibuprofen in healthy volunteers. | 2008-07 |
|
| Chiral separation of ibuprofen and chiral pharmacokinetics in healthy Chinese volunteers. | 2008-06-12 |
|
| Postoperative ketorolac does not predispose to pseudoarthrosis following posterior spinal fusion and instrumentation for adolescent idiopathic scoliosis. | 2008-05-01 |
|
| Dexibuprofen (S(+)-isomer ibuprofen) reduces microglial activation and impairments of spatial working memory induced by chronic lipopolysaccharide infusion. | 2008-05 |
|
| Prescribing pattern of drugs in the treatment of osteoarthritis in Italian general practice: the effect of rofecoxib withdrawal. | 2008-04-15 |
|
| NMR evaluation of adipocyte fatty acid binding protein (aP2) with R- and S-ibuprofen. | 2008-04-15 |
|
| Development of an affinity silica monolith containing human serum albumin for chiral separations. | 2008-04-14 |
|
| Emergency department patient knowledge concerning acetaminophen (paracetamol) in over-the-counter and prescription analgesics. | 2008-04 |
|
| Analgesic synergy between topical opioids and topical non-steroidal anti-inflammatory drugs in the mouse model of thermal pain. | 2008-01-28 |
|
| A randomized, crossover study to determine bioequivalence of two brands of dexibuprofen 400 mg tablets in healthy Asian adult male subjects of Indian origin. | 2008-01 |
|
| Bioequivalence study of two formulations containing 400 mg dexibuprofen in healthy Indian subjects. | 2008 |
|
| Nonsteroidal anti-inflammatory drugs and breast cancer risk in the National Institutes of Health-AARP Diet and Health Study. | 2008 |
|
| Free drug metabolic clearance in elderly people. | 2008 |
|
| The role of peroxisome proliferator-activated receptors in the development and physiology of gametes and preimplantation embryos. | 2008 |
|
| S-ibuprofen effectively inhibits thromboxane B2 levels and platelet function in an experimental model of lipopolysaccharide-stimulated and non-stimulated whole blood. | 2008 |
|
| A review of ibuprofen and acetaminophen use in febrile children and the occurrence of asthma-related symptoms. | 2007-12 |
|
| NMR spectroscopic studies on the in vitro acyl glucuronide migration kinetics of Ibuprofen ((+/-)-(R,S)-2-(4-isobutylphenyl) propanoic acid), its metabolites, and analogues. | 2007-11-15 |
|
| Effectiveness evaluation of available without prescription medicines for postoperative pain treatment after "one day surgery". | 2007-11-07 |
|
| Effect of absorption rate on pharmacokinetics of ibuprofen in relation to chiral inversion in humans. | 2007-11 |
|
| Stereochemical identification of (R)- and (S)-ibuprofen using residual dipolar couplings, NMR, and modeling. | 2007-09 |
|
| The effect of acetaminophen (four grams a day for three consecutive days) on hepatic tests in alcoholic patients--a multicenter randomized study. | 2007-05-30 |
|
| Stereoselective interaction between the CYP2C8 inhibitor gemfibrozil and racemic ibuprofen. | 2007-05 |
|
| A novel method for assessing inhibition of ibuprofen chiral inversion and its application in drug discovery. | 2007-04-20 |
|
| An internet survey of 2,596 people with fibromyalgia. | 2007-03-09 |
|
| 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. | 2007-02-23 |
|
| [Pharmacokinetic interaction between phenitoin and dexibuprofen resulting in acute neurologic toxicity]. | 2007-02-17 |
|
| Synthesis and biological activities of novel dexibuprofen tetraacetylriboflavin conjugates. | 2007-02-01 |
|
| Effects of St. John's wort supplementation on ibuprofen pharmacokinetics. | 2007-02 |
|
| Effects of dexibuprofen on platelet function in humans: comparison with low-dose aspirin. | 2007-02 |
|
| (S)-Ibuprofen-imprinted polymers incorporating gamma-methacryloxypropyl-trimethoxysilane for CEC separation of ibuprofen enantiomers. | 2006-11 |
|
| A comparative study of the pharmacokinetics of ibuprofen arginate versus dexibuprofen in healthy volunteers. | 2006-10 |
|
| Use of triplet excited States for the study of drug binding to human and bovine serum albumins. | 2006-09 |
|
| Optimization of enantioselective resolution of racemic ibuprofen by native lipase from Aspergillus niger. | 2006-08 |
|
| Evidence of COX-2 independent induction of apoptosis and cell cycle block in human colon carcinoma cells after S- or R-ibuprofen treatment. | 2006-07-01 |
|
| [Study on ion beam mutagenizing of the Trichosporon lactis T for enantioselective separation of ibuprofen]. | 2006-04 |
|
| Modification of pepsinogen I levels and their correlation with gastrointestinal injury after administration of dexibuprofen, ibuprofen or diclofenac: a randomized, open-label, controlled clinical trial. | 2006-04 |
|
| Beyond the white coat ceremony. | 2006-03 |
|
| Increased expression of cyclooxygenase and nitric oxide isoforms, and exaggerated sensitivity to prostaglandin E2, in the rat lumbar spinal cord 3 days after L5-L6 spinal nerve ligation. | 2006-02 |
|
| Application of thin-layer chromatography to investigate oscillatory instability of the selected profen enantiomers in dichloromethane. | 2006-01-28 |
|
| Bioequivalence study of two Ibuprofen formulations administered intravenously in healthy male volunteers. | 2004 |
Patents
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
T179MT9211
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| Record Status |
Validated (UNII)
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| Record Version |
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141505-32-0
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m6189
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DTXSID60931109
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T179MT9211
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C169895
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300000021796
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