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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
Structure of DEXIBUPROFEN LYSINE ANHYDROUS

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

HIDE SMILES / InChI

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

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

Targets
PubMed

PubMed

TitleDatePubMed
The enantioselective immunoaffinity extraction of an optically active ibuprofen-modified peptide fragment.
2001 Sep 1
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
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
Dexibuprofen (S+-isomer ibuprofen) reduces gastric damage and improves analgesic and antiinflammatory effects in rodents.
2003 Aug
Enantioselective immunorecognition of protein modification with optically active ibuprofen using polyclonal antibody.
2004 Jun 25
Application of thin-layer chromatography to investigate oscillatory instability of the selected profen enantiomers in dichloromethane.
2005 Nov-Dec
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
Optimization of enantioselective resolution of racemic ibuprofen by native lipase from Aspergillus niger.
2006 Aug
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
Beyond the white coat ceremony.
2006 Mar
Dynamic kinetic resolution: alternative approach in optimizing S-ibuprofen production.
2006 Mar
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
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
Free drug metabolic clearance in elderly people.
2008
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
Formulation of a extended release tablet containing dexibuprofen.
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
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
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
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:19:57 GMT 2025
Edited
by admin
on Mon Mar 31 21:19:57 GMT 2025
Record UNII
B5VWM9PYNC
Record Status Validated (UNII)
Record Version
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Name Type Language
DEXIBUPROFEN LYSINE ANHYDROUS
Common Name English
(+)-(S)-P-ISOBUTYLHYDRATROPIC ACID, COMPOUND WITH L-LYSINE (1:1)
Preferred Name English
BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (S)-, COMPD. WITH L-LYSINE (1:1)
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID70150405
Created by admin on Mon Mar 31 21:19:57 GMT 2025 , Edited by admin on Mon Mar 31 21:19:57 GMT 2025
PRIMARY
CAS
113403-10-4
Created by admin on Mon Mar 31 21:19:57 GMT 2025 , Edited by admin on Mon Mar 31 21:19:57 GMT 2025
PRIMARY
FDA UNII
B5VWM9PYNC
Created by admin on Mon Mar 31 21:19:57 GMT 2025 , Edited by admin on Mon Mar 31 21:19:57 GMT 2025
PRIMARY
PUBCHEM
9819902
Created by admin on Mon Mar 31 21:19:57 GMT 2025 , Edited by admin on Mon Mar 31 21:19:57 GMT 2025
PRIMARY
SMS_ID
300000021795
Created by admin on Mon Mar 31 21:19:57 GMT 2025 , Edited by admin on Mon Mar 31 21:19:57 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY