U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H18O2
Molecular Weight 206.2808
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXIBUPROFEN

SMILES

CC(C)CC1=CC=C(C=C1)[C@H](C)C(O)=O

InChI

InChIKey=HEFNNWSXXWATRW-JTQLQIEISA-N
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/m0/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

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
Effectiveness evaluation of available without prescription medicines for postoperative pain treatment after "one day surgery".
2001 Jul-Sep
Aseptic meningo-encephalitis related to dexibuprofen use in a patient with systemic lupus erythematosus: a case report with MR findings.
2002
Stereoselectivity of ibuprofen metabolism and pharmacokinetics following the administration of the racemate to healthy volunteers.
2002 Aug
The cyclooxygenase inhibitor ibuprofen and the FLAP inhibitor MK886 inhibit pancreatic carcinogenesis induced in hamsters by transplacental exposure to ethanol and the tobacco carcinogen NNK.
2002 Oct
Enantioselective analysis of ibuprofen in human plasma by anionic cyclodextrin-modified electrokinetic chromatography.
2002 Sep
Dexibuprofen: pharmacology, therapeutic uses and safety.
2003
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
Dexibuprofen (S+-isomer ibuprofen) reduces gastric damage and improves analgesic and antiinflammatory effects in rodents.
2003 Aug
Regio- and enantiospecific rhodium-catalyzed arylation of unsymmetrical fluorinated acyclic allylic carbonates: inversion of absolute configuration.
2003 Jun 18
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
Interindividual variability in ibuprofen pharmacokinetics is related to interaction of cytochrome P450 2C8 and 2C9 amino acid polymorphisms.
2004 Aug
Synthesis and evaluation of S-4-(3-thienyl)phenyl-alpha-methylacetic acid.
2004 Feb 23
Highly enantioselective separation using a supported liquid membrane encapsulating surfactant-enzyme complex.
2004 Jul 21
Enantioselective immunorecognition of protein modification with optically active ibuprofen using polyclonal antibody.
2004 Jun 25
Population pharmacokinetics of ibuprofen enantiomers in very premature neonates.
2004 Oct
Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins.
2005
Solid-phase microextraction and chiral HPLC analysis of ibuprofen in urine.
2005 Apr 25
A supported liquid membrane encapsulating a surfactant-lipase complex for the selective separation of organic acids.
2005 Feb 4
Perioperative pharmacokinetics of ibuprofen enantiomers after rectal administration.
2005 Jul
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
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
Dynamic kinetic resolution: alternative approach in optimizing S-ibuprofen production.
2006 Mar
Use of triplet excited States for the study of drug binding to human and bovine serum albumins.
2006 Sep
A review of ibuprofen and acetaminophen use in febrile children and the occurrence of asthma-related symptoms.
2007 Dec
Effects of dexibuprofen on platelet function in humans: comparison with low-dose aspirin.
2007 Feb
[Pharmacokinetic interaction between phenitoin and dexibuprofen resulting in acute neurologic toxicity].
2007 Feb 17
An internet survey of 2,596 people with fibromyalgia.
2007 Mar 9
Stereoselective interaction between the CYP2C8 inhibitor gemfibrozil and racemic ibuprofen.
2007 May
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
Bioequivalence study of two formulations containing 400 mg dexibuprofen in healthy Indian subjects.
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
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
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
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
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
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 Fri Dec 15 15:32:15 GMT 2023
Edited
by admin
on Fri Dec 15 15:32:15 GMT 2023
Record UNII
671DKG7P5S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXIBUPROFEN
INN   MART.   USAN   WHO-DD  
USAN   INN  
Official Name English
(S)-IBUPROFEN
Common Name English
S-IBUPROFEN
Common Name English
DEXIBUPROFEN [USAN]
Common Name English
dexibuprofen [INN]
Common Name English
Dexibuprofen [WHO-DD]
Common Name English
BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (S)-
Common Name English
DEXIBUPROFEN [MART.]
Common Name English
(+)-(S)-P-ISOBUTYLHYDRATROPIC ACID
Common Name English
NSC-759814
Code English
Classification Tree Code System Code
WHO-ATC M01AE14
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
WHO-VATC QM01AE14
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C166907
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
EVMPD
SUB07030MIG
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
SMS_ID
100000083204
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
DRUG CENTRAL
3851
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
CAS
51146-56-6
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
USAN
JJ-29
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
WIKIPEDIA
DEXIBUPROFEN
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
CHEBI
43415
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
PUBCHEM
39912
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
MESH
C539402
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
NSC
759814
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID9048724
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL175
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
DRUG BANK
DB09213
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
FDA UNII
671DKG7P5S
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
INN
6426
Created by admin on Fri Dec 15 15:32:15 GMT 2023 , Edited by admin on Fri Dec 15 15:32:15 GMT 2023
PRIMARY
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