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

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
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Indoprofen is one of several NSAIDs that have been withdrawn from the market due to causing severe gastrointestinal bleeding.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
The non-steroidal anti-inflammatory drug, indomethacin, as an inhibitor of HIV replication.	1995 Feb 20	7875307
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
A three-component coupling process based on vicarious nucleophilic substitution (VNS(AR))-alkylation reactions: an approach to indoprofen and derivatives.	2002 Jan 25	11798318
Optimization of sample stacking for the simultaneous determination of nonsteroidal anti-inflammatory drugs with a wall-coated histidine capillary column.	2004 Feb	14981683
DNA photosensitization by indoprofen - is DNA damage photoinduced by indoprofen or by its photoproducts?	2004 Feb	14872241
Investigating the potential of erythromycin and derivatives as chiral selector in capillary electrophoresis.	2004 Mar 10	15019020
Effect of anti-inflammatory drugs on splenocyte membrane fluidity.	2005 Apr 1	15766721
Comparative study of the photophysical properties of indoprofen photoproducts in relation with their DNA photosensitizing properties.	2005 Mar	15738999
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
Chiral ionic liquids for enantioseparation of pharmaceutical products by capillary electrophoresis.	2008 Sep 19	18440541
Enantiomeric separation of 2-arylpropionic acid nonsteroidal anti-inflammatory drugs by HPLC with hydroxypropyl-beta-cyclodextrin as chiral mobile phase additive.	2010 Aug	20017213
Spinal muscular atrophy disease: a literature review for therapeutic strategies.	2010 Jan-Mar	20302191
Discovery, synthesis, and biological evaluation of novel SMN protein modulators.	2011 Sep 22	21819082

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:25:18 GMT 2023` Edited by `admin` on `Fri Dec 15 15:25:18 GMT 2023`
Record UNII	CPE46ZU14N
Record Status	`Validated (UNII)`
Record Version

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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