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 |
---|---|---|
Synthesis of (S)-ibuprofen via enantioselective degradation of racemic ibuprofen with an isolated yeast, Trichosporon cutaneum KPY 30802, in an interface bioreactor. | 2001 |
|
The enantioselective immunoaffinity extraction of an optically active ibuprofen-modified peptide fragment. | 2001 Sep 1 |
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In vitro detection of (S)-naproxen and ibuprofen binding to plaques in the Alzheimer's brain using the positron emission tomography molecular imaging probe 2-(1-[6-[(2-[(18)F]fluoroethyl)(methyl)amino]-2-naphthyl]ethylidene)malononitrile. | 2003 |
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Inhibition of spinal prostaglandin synthesis early after L5/L6 nerve ligation prevents the development of prostaglandin-dependent and prostaglandin-independent allodynia in the rat. | 2003 Nov |
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Aspirin use and lung cancer in men. | 2003 Nov 3 |
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Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins. | 2005 |
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Application of thin-layer chromatography to investigate oscillatory instability of the selected profen enantiomers in dichloromethane. | 2005 Nov-Dec |
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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 Apr |
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Chromatographic analysis of allosteric effects between ibuprofen and benzodiazepines on human serum albumin. | 2006 Jan |
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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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Bioequivalence study of two formulations containing 400 mg dexibuprofen in healthy Indian subjects. | 2008 |
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Prescribing pattern of drugs in the treatment of osteoarthritis in Italian general practice: the effect of rofecoxib withdrawal. | 2008 Apr 15 |
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Population pharmacokinetic analysis of Ibuprofen enantiomers in preterm newborn infants. | 2008 Dec |
|
Dexibuprofen (S(+)-isomer ibuprofen) reduces microglial activation and impairments of spatial working memory induced by chronic lipopolysaccharide infusion. | 2008 May |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:05:08 GMT 2025
by
admin
on
Mon Mar 31 18:05:08 GMT 2025
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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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11954362
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AA-56
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T179MT9211
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C169895
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300000021796
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |