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
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
Effectiveness evaluation of available without prescription medicines for postoperative pain treatment after "one day surgery".
2001 Jul-Sep
Efficacy and long-term safety of dexibuprofen [S(+)-ibuprofen]: a short-term efficacy study in patients with osteoarthritis of the hip and a 1-year tolerability study in patients with rheumatic disorders.
2001 Nov
Treatment of non-malignant pain in the Dutch GP population: an analysis of treatment standards, prescription habits and basic attitudes.
2001 Nov
Ibuprofen interference in the determination of 3-phenoxybenzoic acid in urine.
2001 Nov
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
Enantioselective release of controlled delivery granules based on molecularly imprinted polymers.
2002 Jan-Mar
Enantiospecific effects of cytochrome P450 2C9 amino acid variants on ibuprofen pharmacokinetics and on the inhibition of cyclooxygenases 1 and 2.
2002 Jul
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
Dexibuprofen: pharmacology, therapeutic uses and safety.
2003
Influence of age on the enantiomeric disposition of ibuprofen in healthy volunteers.
2003 Jun
Synthesis and evaluation of S-4-(3-thienyl)phenyl-alpha-methylacetic acid.
2004 Feb 23
Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins.
2005
A supported liquid membrane encapsulating a surfactant-lipase complex for the selective separation of organic acids.
2005 Feb 4
The interaction of lipophilic drugs with intestinal fatty acid-binding protein.
2005 May 6
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
[Study on ion beam mutagenizing of the Trichosporon lactis T for enantioselective separation of ibuprofen].
2006 Apr
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
Binding studies of taxanes to human serum albumin by bioaffinity chromatography and circular dichroism.
2006 Sep 11
A novel method for assessing inhibition of ibuprofen chiral inversion and its application in drug discovery.
2007 Apr 20
A review of ibuprofen and acetaminophen use in febrile children and the occurrence of asthma-related symptoms.
2007 Dec
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
Effect of absorption rate on pharmacokinetics of ibuprofen in relation to chiral inversion in humans.
2007 Nov
Free drug metabolic clearance in elderly people.
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
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
Population pharmacokinetic analysis of Ibuprofen enantiomers in preterm newborn infants.
2008 Dec
Analgesic synergy between topical opioids and topical non-steroidal anti-inflammatory drugs in the mouse model of thermal pain.
2008 Jan 28
Dexibuprofen (S(+)-isomer ibuprofen) reduces microglial activation and impairments of spatial working memory induced by chronic lipopolysaccharide infusion.
2008 May
Impaired intrinsic chiral inversion activity of ibuprofen in rats with adjuvant-induced arthritis.
2008 Nov
Influence of benzylamine on the resolution of ibuprofen with (+)-(R)-phenylethylamine via supercritical fluid extraction.
2009 Jun
Patents
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