Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H18O2.C6H14N2O2 |
| Molecular Weight | 352.4684 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCC[C@H](N)C(O)=O.CC(C)CC1=CC=C(C=C1)[C@H](C)C(O)=O
InChI
InChIKey=IHHXIUAEPKVVII-PTKYJSHISA-N
InChI=1S/C13H18O2.C6H14N2O2/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)/t10-;5-/m00/s1
| 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 |
| 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 |
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 |
|---|---|---|
| Synthesis of (S)-ibuprofen via enantioselective degradation of racemic ibuprofen with an isolated yeast, Trichosporon cutaneum KPY 30802, in an interface bioreactor. | 2001 |
|
| Effectiveness evaluation of available without prescription medicines for postoperative pain treatment after "one day surgery". | 2001 Jul-Sep |
|
| Bioequivalence study of two Ibuprofen formulations administered intravenously in healthy male volunteers. | 2004 |
|
| Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins. | 2005 |
|
| Enantioselective pharmacokinetics of ibuprofen and involved mechanisms. | 2005 |
|
| The effect of a dexibuprofen mouth rinse on experimental gingivitis in humans. | 2005 Jun |
|
| An eutomer/distomer ratio near unity does not justify non-enantiospecific assay methods in bioequivalence studies. | 2005 Oct |
|
| Similarity in structures of racemic and enantiomeric ibuprofen sodium dihydrates. | 2005 Sep |
|
| 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 Feb |
|
| Beyond the white coat ceremony. | 2006 Mar |
|
| (S)-Ibuprofen-imprinted polymers incorporating gamma-methacryloxypropyl-trimethoxysilane for CEC separation of ibuprofen enantiomers. | 2006 Nov |
|
| Binding studies of taxanes to human serum albumin by bioaffinity chromatography and circular dichroism. | 2006 Sep 11 |
|
| A novel method for assessing inhibition of ibuprofen chiral inversion and its application in drug discovery. | 2007 Apr 20 |
|
| A review of ibuprofen and acetaminophen use in febrile children and the occurrence of asthma-related symptoms. | 2007 Dec |
|
| Effects of St. John's wort supplementation on ibuprofen pharmacokinetics. | 2007 Feb |
|
| Effects of dexibuprofen on platelet function in humans: comparison with low-dose aspirin. | 2007 Feb |
|
| Synthesis and biological activities of novel dexibuprofen tetraacetylriboflavin conjugates. | 2007 Feb 1 |
|
| [Pharmacokinetic interaction between phenitoin and dexibuprofen resulting in acute neurologic toxicity]. | 2007 Feb 17 |
|
| 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 |
|
| An internet survey of 2,596 people with fibromyalgia. | 2007 Mar 9 |
|
| Stereoselective interaction between the CYP2C8 inhibitor gemfibrozil and racemic ibuprofen. | 2007 May |
|
| The effect of acetaminophen (four grams a day for three consecutive days) on hepatic tests in alcoholic patients--a multicenter randomized study. | 2007 May 30 |
|
| Effect of absorption rate on pharmacokinetics of ibuprofen in relation to chiral inversion in humans. | 2007 Nov |
|
| 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 Nov 15 |
|
| Stereochemical identification of (R)- and (S)-ibuprofen using residual dipolar couplings, NMR, and modeling. | 2007 Sep |
|
| 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 |
|
| Emergency department patient knowledge concerning acetaminophen (paracetamol) in over-the-counter and prescription analgesics. | 2008 Apr |
|
| Development of an affinity silica monolith containing human serum albumin for chiral separations. | 2008 Apr 14 |
|
| Prescribing pattern of drugs in the treatment of osteoarthritis in Italian general practice: the effect of rofecoxib withdrawal. | 2008 Apr 15 |
|
| NMR evaluation of adipocyte fatty acid binding protein (aP2) with R- and S-ibuprofen. | 2008 Apr 15 |
|
| 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 Aug 26 |
|
| Formulation of a extended release tablet containing dexibuprofen. | 2008 Dec |
|
| The effects and safety of dexibuprofen compared with ibuprofen in febrile children caused by upper respiratory tract infection. | 2008 Dec |
|
| Population pharmacokinetic analysis of Ibuprofen enantiomers in preterm newborn infants. | 2008 Dec |
|
| 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 Jan |
|
| Analgesic synergy between topical opioids and topical non-steroidal anti-inflammatory drugs in the mouse model of thermal pain. | 2008 Jan 28 |
|
| Chiral separation of ibuprofen and chiral pharmacokinetics in healthy Chinese volunteers. | 2008 Jan-Mar |
|
| Influence of CYP2C8 and CYP2C9 polymorphisms on pharmacokinetic and pharmacodynamic parameters of racemic and enantiomeric forms of ibuprofen in healthy volunteers. | 2008 Jul |
|
| Dexibuprofen (S(+)-isomer ibuprofen) reduces microglial activation and impairments of spatial working memory induced by chronic lipopolysaccharide infusion. | 2008 May |
|
| Postoperative ketorolac does not predispose to pseudoarthrosis following posterior spinal fusion and instrumentation for adolescent idiopathic scoliosis. | 2008 May 1 |
|
| Impaired intrinsic chiral inversion activity of ibuprofen in rats with adjuvant-induced arthritis. | 2008 Nov |
|
| Enantioselective formation of ibuprofen-S-acyl-glutathione in vitro in incubations of ibuprofen with rat hepatocytes. | 2008 Sep |
|
| Characterization of drug-protein binding process by employing equilibrium sampling through hollow-fiber supported liquid membrane and Bjerrum and Scatchard plots. | 2008 Sep 10 |
|
| ADIDAC trial: analgesia with dexibuprofen versus ibuprofen in patients suffering from primary dysmenorrhea: a crossover trial. | 2009 |
|
| Influence of benzylamine on the resolution of ibuprofen with (+)-(R)-phenylethylamine via supercritical fluid extraction. | 2009 Jun |
|
| Cyclic resolution of racemic ibuprofen via coupled efficient lipase and acid-base catalysis. | 2009 Mar |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 03:58:56 GMT 2023
by
admin
on
Sat Dec 16 03:58:56 GMT 2023
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| Record UNII |
B5VWM9PYNC
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID70150405
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113403-10-4
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B5VWM9PYNC
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9819902
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300000021795
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |