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 | 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 | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| The oral bioavailability of ibuprofen enantiomers in broiler chickens. | 2001 Apr |
|
| Radical degradation of high molecular weight hyaluronan: inhibition of the reaction by ibuprofen enantiomers. | 2001 Mar |
|
| Pain treatment with NSAIDs, primary focus on ibuprofen. | 2001 Nov |
|
| Enantiospecific effects of cytochrome P450 2C9 amino acid variants on ibuprofen pharmacokinetics and on the inhibition of cyclooxygenases 1 and 2. | 2002 Jul |
|
| Dexibuprofen: pharmacology, therapeutic uses and safety. | 2003 |
|
| Bioavailability of two dermal formulations of S(+)ibuprofen in rabbit. | 2003 |
|
| Ask the doctors. I have arthritis and take Motrin. Is there a problem with also taking aspirin, since my doctor has told me to do this ever since my heart attack? | 2003 Apr |
|
| Comparison of the efficacy and tolerability of dexibuprofen and celecoxib in the treatment of osteoarthritis of the hip. | 2003 Apr |
|
| Quantitative analysis of allosteric drug-protein binding by biointeraction chromatography. | 2004 Nov |
|
| Enantioselective pharmacokinetics of ibuprofen and involved mechanisms. | 2005 |
|
| A supported liquid membrane encapsulating a surfactant-lipase complex for the selective separation of organic acids. | 2005 Feb 4 |
|
| The effect of a dexibuprofen mouth rinse on experimental gingivitis in humans. | 2005 Jun |
|
| Application of thin-layer chromatography to investigate oscillatory instability of the selected profen enantiomers in dichloromethane. | 2005 Nov-Dec |
|
| 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 |
|
| 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 |
|
| (S)-Ibuprofen-imprinted polymers incorporating gamma-methacryloxypropyl-trimethoxysilane for CEC separation of ibuprofen enantiomers. | 2006 Nov |
|
| A comparative study of the pharmacokinetics of ibuprofen arginate versus dexibuprofen in healthy volunteers. | 2006 Oct |
|
| A novel method for assessing inhibition of ibuprofen chiral inversion and its application in drug discovery. | 2007 Apr 20 |
|
| 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 |
|
| 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 |
|
| Stereochemical identification of (R)- and (S)-ibuprofen using residual dipolar couplings, NMR, and modeling. | 2007 Sep |
|
| Free drug metabolic clearance in elderly people. | 2008 |
|
| Development of an affinity silica monolith containing human serum albumin for chiral separations. | 2008 Apr 14 |
|
| 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 |
|
| Postoperative ketorolac does not predispose to pseudoarthrosis following posterior spinal fusion and instrumentation for adolescent idiopathic scoliosis. | 2008 May 1 |
|
| Cyclic resolution of racemic ibuprofen via coupled efficient lipase and acid-base catalysis. | 2009 Mar |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:40:33 GMT 2023
by
admin
on
Fri Dec 15 15:40:33 GMT 2023
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| Record UNII |
T179MT9211
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| Record Status |
Validated (UNII)
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m6189
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T179MT9211
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300000021796
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ACTIVE MOIETY |