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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
Structure of DEXIBUPROFEN LYSINE

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

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 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

Targets
PubMed

PubMed

TitleDatePubMed
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
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
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
Aspirin use and lung cancer in men.
2003 Nov 3
Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins.
2005
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
Chromatographic analysis of allosteric effects between ibuprofen and benzodiazepines on human serum albumin.
2006 Jan
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
Dynamic kinetic resolution: alternative approach in optimizing S-ibuprofen production.
2006 Mar
Bioequivalence study of two formulations containing 400 mg dexibuprofen in healthy Indian subjects.
2008
Prescribing pattern of drugs in the treatment of osteoarthritis in Italian general practice: the effect of rofecoxib withdrawal.
2008 Apr 15
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 Mon Mar 31 18:05:08 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:08 GMT 2025
Record UNII
T179MT9211
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXIBUPROFEN LYSINE
USAN   WHO-DD  
USAN  
Official Name English
IBUPROFEN S-FORM L-LYSINE SALT MONOHYDRATE
MI  
Preferred Name English
BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (S)-, COMPD. WITH L-LYSINE (1:1) MONOHYDRATE
Common Name English
L-669,455
Code English
DEXIBUPROFEN LYSINE [USAN]
Common Name English
DOCTRIN
Brand Name English
IBUPROFEN S-FORM L-LYSINE SALT MONOHYDRATE [MI]
Common Name English
(+)-(S)-P-ISOBUTYLHYDRATROPIC ACID, COMPOUND WITH L-LYSINE (1:1), MONOHYDRATE
Common Name English
MK-233
Code English
L-669455
Code English
Dexibuprofen lysine [WHO-DD]
Common Name English
Code System Code Type Description
CAS
141505-32-0
Created by admin on Mon Mar 31 18:05:08 GMT 2025 , Edited by admin on Mon Mar 31 18:05:08 GMT 2025
PRIMARY
MERCK INDEX
m6189
Created by admin on Mon Mar 31 18:05:08 GMT 2025 , Edited by admin on Mon Mar 31 18:05:08 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID60931109
Created by admin on Mon Mar 31 18:05:08 GMT 2025 , Edited by admin on Mon Mar 31 18:05:08 GMT 2025
PRIMARY
PUBCHEM
11954362
Created by admin on Mon Mar 31 18:05:08 GMT 2025 , Edited by admin on Mon Mar 31 18:05:08 GMT 2025
PRIMARY
USAN
AA-56
Created by admin on Mon Mar 31 18:05:08 GMT 2025 , Edited by admin on Mon Mar 31 18:05:08 GMT 2025
PRIMARY
FDA UNII
T179MT9211
Created by admin on Mon Mar 31 18:05:08 GMT 2025 , Edited by admin on Mon Mar 31 18:05:08 GMT 2025
PRIMARY
NCI_THESAURUS
C169895
Created by admin on Mon Mar 31 18:05:08 GMT 2025 , Edited by admin on Mon Mar 31 18:05:08 GMT 2025
PRIMARY
SMS_ID
300000021796
Created by admin on Mon Mar 31 18:05:08 GMT 2025 , Edited by admin on Mon Mar 31 18:05:08 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY