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Details

Stereochemistry RACEMIC
Molecular Formula C17H15NO3
Molecular Weight 281.3059
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOPROFEN

SMILES

CC(C(O)=O)C1=CC=C(C=C1)N2CC3=C(C=CC=C3)C2=O

InChI

InChIKey=RJMIEHBSYVWVIN-UHFFFAOYSA-N
InChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21)

HIDE SMILES / InChI
Molecular Formula C17H15NO3
Molecular Weight 281.3059
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Indoprofen is one of several NSAIDs that have been withdrawn from the market due to causing severe gastrointestinal bleeding. The UK Licensing Authority suspended the product license on grounds of safety in 1983 and in 1984 the Italian manufacturers decided to withdraw it from the world market. The UK decision was taken because there was a high rate of adverse drug reactions in a voluntary postmarketing surveillance study and the spontaneous adverse reaction reporting system had noted 217 serious adverse effects, mainly gastrointestinal bleeding and perforation.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 21.0 µM [IC50]
Inhibitor
8504
Binding Agent
1076
 1.27 µM [Ki]
PubMed

PubMed

TitleDatePubMed
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015-01-05
Discovery, synthesis, and biological evaluation of novel SMN protein modulators.
2011-09-22
"Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography.
2010-12-10
Enantiomeric separation of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs by HPLC with hydroxypropyl-beta-cyclodextrin as chiral mobile phase additive.
2010-08
Spinal muscular atrophy disease: a literature review for therapeutic strategies.
2010-03-23
Enantiomeric separation of acidic compounds by nano-liquid chromatography with methylated-beta-cyclodextrin as a mobile phase additive.
2009-05
Alternative splicing of exon 10 in the tau gene as a target for treatment of tauopathies.
2008-12-03
Ca(2+) signaling occurs via second messenger release from intraorganelle synthesis sites.
2008-10-28
Chiral ionic liquids for enantioseparation of pharmaceutical products by capillary electrophoresis.
2008-09-19
Dexibuprofen (S(+)-isomer ibuprofen) reduces microglial activation and impairments of spatial working memory induced by chronic lipopolysaccharide infusion.
2008-05
Isoindol-1,3-dione and isoindol-1-one derivatives with high binding affinity to beta-amyloid fibrils.
2008-03-01
A randomized, crossover study to determine bioequivalence of two brands of dexibuprofen 400 mg tablets in healthy Asian adult male subjects of Indian origin.
2008-01
Singlet oxygen scavenging activity of non-steroidal anti-inflammatory drugs.
2008
Antioxidant activity and inhibition of human neutrophil oxidative burst mediated by arylpropionic acid non-steroidal anti-inflammatory drugs.
2006-08
Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography.
2006-08
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.
2006-04
Use of vancomycin chiral stationary phase for the enantiomeric resolution of basic and acidic compounds by nano-liquid chromatography.
2005-07-15
The effect of a dexibuprofen mouth rinse on experimental gingivitis in humans.
2005-06
Effect of anti-inflammatory drugs on splenocyte membrane fluidity.
2005-04-01
Phase behavior of amorphous molecular dispersions II: Role of hydrogen bonding in solid solubility and phase separation kinetics.
2005-03
Comparative study of the photophysical properties of indoprofen photoproducts in relation with their DNA photosensitizing properties.
2005-03
Indoprofen upregulates the survival motor neuron protein through a cyclooxygenase-independent mechanism.
2004-11
Cationic vesicles as chiral selector for enantioseparations of nonsteroidal antiinflammatory drugs by micellar electrokinetic chromatography.
2004-09-03
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
2004-07-02
Investigating the potential of erythromycin and derivatives as chiral selector in capillary electrophoresis.
2004-03-10
Optimization of sample stacking for the simultaneous determination of nonsteroidal anti-inflammatory drugs with a wall-coated histidine capillary column.
2004-02
DNA photosensitization by indoprofen - is DNA damage photoinduced by indoprofen or by its photoproducts?
2004-02
Photochemical and photophysical properties of indoprofen.
2003-05
Capillary electrochromatographic separation of non-steroidal anti-inflammatory drugs with a histidine bonded phase.
2002-12-27
A three-component coupling process based on vicarious nucleophilic substitution (VNS(AR))-alkylation reactions: an approach to indoprofen and derivatives.
2002-01-25
Aseptic meningo-encephalitis related to dexibuprofen use in a patient with systemic lupus erythematosus: a case report with MR findings.
2002
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001-11
Recognition of cyclooxygenase-2 (COX-2) active site by NSAIDs: a computer modelling study.
2001-09-21
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg.
2001-01-10
The non-steroidal anti-inflammatory drug, indomethacin, as an inhibitor of HIV replication.
1995-02-20
Duodenogastric reflux and gastric damage from non-steroidal antiinflammatory drugs.
1986
A double-blind evaluation of oral indoprofen versus ASA in osteoarthritic patients: influence on haemostatic parameters and clinical effects.
1981
Patents

Patents

20010002262
19
JP2003515526A
470
JPS5432464A
2
JPS5750961A
2
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:57:06 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:06 GMT 2025
Record UNII
CPE46ZU14N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDOPROFEN
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
BOR-IND
Preferred Name English
2-(4-(1-OXO-2-ISOINDOLINYL)PHENYL)PROPIONIC ACID
Systematic Name English
IPP
Common Name English
P-(1-OXO-2-ISOINDOLINYL)HYDRATROPIC ACID
Common Name English
REUMOFENE
Brand Name English
K-4277
Code English
Indoprofen [WHO-DD]
Common Name English
INDOPROFEN [USAN]
Common Name English
NSC-757065
Code English
ISINDONE
Brand Name English
indoprofen [INN]
Common Name English
PRAXIS
Brand Name English
INDOPROFEN [MI]
Common Name English
BENZENEACETIC ACID, 4-(1,3-DIHYDRO-1-OXO-2H-ISOINDOL-2-YL)-.ALPHA.-METHYL-
Common Name English
FLOSINT
Brand Name English
K 4277
Code English
FLOSIN
Brand Name English
4-(1,3-DIHYDRO-1-OXO-2H-ISOINDOL-2-YL)-.ALPHA.-METHYLBENZENEACETIC ACID
Systematic Name English
1-OXO-2-(P-((.ALPHA.-METHYL)CARBOXYMETHYL)PHENYL)ISOINDOLINE
Common Name English
2-(4-(1-CARBOXYETHYL)PHENYL)-1-ISOINDOLINONE
Systematic Name English
INDOPROFEN [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QM01AE10
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
WHO-ATC M01AE10
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
NCI_THESAURUS C257
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
Code System Code Type Description
SMS_ID
100000083395
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
INN
3689
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID5045831
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
EVMPD
SUB08183MIG
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
MERCK INDEX
m771
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY Merck Index
CAS
31842-01-0
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
NCI_THESAURUS
C83801
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
CAS
53022-60-9
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
SUPERSEDED
NSC
757065
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
PUBCHEM
3718
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
ECHA (EC/EINECS)
250-833-0
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
FDA UNII
CPE46ZU14N
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
DRUG CENTRAL
1442
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
ChEMBL
CHEMBL15870
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
MESH
D007216
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
CHEBI
76162
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
WIKIPEDIA
INDOPROFEN
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
DRUG BANK
DB08951
Created by admin on Mon Mar 31 17:57:06 GMT 2025 , Edited by admin on Mon Mar 31 17:57:06 GMT 2025
PRIMARY
Related Record Type Details
Structure of DEXINDOPROFEN
ENANTIOMER -> RACEMATE
Structure of INDOPROFEN, (-)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of INDOPROFEN
ACTIVE MOIETY
NIH
NCATS
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