INDOPROFEN

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 Search

SMILES

CC(C(O)=O)C1=CC=C(C=C1)N2CC3=CC=CC=C3C2=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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3514486 | https://www.ncbi.nlm.nih.gov/pubmed/14872241 | https://www.ncbi.nlm.nih.gov/pubmed/6490241

Indoprofen is one of several NSAIDs that have been withdrawn from the market due to causing severe gastrointestinal bleeding.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

Targets

Primary Target	Pharmacology	Potency
Pyruvate kinase isozymes M1/M2 12 Target ID: CHEMBL1075189 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26951145	Inhibitor 8297	21.0 µM [IC50]
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11563332\|https://www.ncbi.nlm.nih.gov/pubmed/3141302\|https://www.ncbi.nlm.nih.gov/pubmed/10217458	Inhibitor 8297
Fatty acid-binding protein, liver 2 Target ID: CHEMBL5738 Sources: http://drugcentral.org/drugcard/1442	Binding Agent 1064	1.27 µM [Ki]

PubMed

Title	Date	PubMed
Duodenogastric reflux and gastric damage from non-steroidal antiinflammatory drugs.	1986	3949444
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Aseptic meningo-encephalitis related to dexibuprofen use in a patient with systemic lupus erythematosus: a case report with MR findings.	2002	12195787
Photochemical and photophysical properties of indoprofen.	2003 May	12812289
DNA photosensitization by indoprofen - is DNA damage photoinduced by indoprofen or by its photoproducts?	2004 Feb	14872241
Indoprofen upregulates the survival motor neuron protein through a cyclooxygenase-independent mechanism.	2004 Nov	15555999
Cationic vesicles as chiral selector for enantioseparations of nonsteroidal antiinflammatory drugs by micellar electrokinetic chromatography.	2004 Sep 3	15453427
Use of vancomycin chiral stationary phase for the enantiomeric resolution of basic and acidic compounds by nano-liquid chromatography.	2005 Jul 15	16013606
The effect of a dexibuprofen mouth rinse on experimental gingivitis in humans.	2005 Jun	15882220
Phase behavior of amorphous molecular dispersions II: Role of hydrogen bonding in solid solubility and phase separation kinetics.	2005 Mar	15835750
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	16625984
Enantiomeric separation of acidic compounds by nano-liquid chromatography with methylated-beta-cyclodextrin as a mobile phase additive.	2009 May	19370733
Enantiomeric separation of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs by HPLC with hydroxypropyl-beta-cyclodextrin as chiral mobile phase additive.	2010 Aug	20017213
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015 Jan 5	25455453

Patents

Name

Type

Language

INDOPROFEN

Official 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

BOR-IND

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