Indoprofen

Identification

Name
Indoprofen
Accession Number
DB08951
Type
Small Molecule
Groups
Withdrawn
Description

A drug that has analgesic and anti-inflammatory properties. Following reports of adverse reactions including reports of carcinogenicity in animal studies it was withdrawn from the market worldwide.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
CPE46ZU14N
CAS number
31842-01-0
Weight
Average: 281.3059
Monoisotopic: 281.105193351
Chemical Formula
C17H15NO3
InChI Key
RJMIEHBSYVWVIN-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-[4-(1-oxo-2,3-dihydro-1H-isoindol-2-yl)phenyl]propanoic acid
SMILES
CC(C(O)=O)C1=CC=C(C=C1)N1CC2=CC=CC=C2C1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Glucuronidation.

Route of elimination
Not Available
Half life

2.3 hours.

Clearance

Renal.

Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Indoprofen.
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when Indoprofen is combined with 16-Bromoepiandrosterone.
19-norandrostenedioneThe risk or severity of adverse effects can be increased when Indoprofen is combined with 19-norandrostenedione.
5-androstenedioneThe risk or severity of adverse effects can be increased when Indoprofen is combined with 5-androstenedione.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Indoprofen is combined with Abciximab.
AcebutololIndoprofen may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Indoprofen is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Indoprofen is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Indoprofen is combined with Acenocoumarol.
AcetaminophenIndoprofen may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,767,805.

General References
  1. Sivelli R, Farinon AM, Ghirarduzzi A, Rinetti M: Duodenogastric reflux and gastric damage from non-steroidal antiinflammatory drugs. Int J Tissue React. 1986;8(1):61-6. [PubMed:3949444]
External Links
KEGG Drug
D04530
PubChem Compound
3718
PubChem Substance
310264916
ChemSpider
3587
BindingDB
50233673
ChEBI
76162
ChEMBL
CHEMBL15870
Wikipedia
Indoprofen
ATC Codes
M01AE10 — Indoprofen

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)208-210U.S. Patent 3,767,805.
Predicted Properties
PropertyValueSource
Water Solubility0.128 mg/mLALOGPS
logP2.44ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.14 m3·mol-1ChemAxon
Polarizability30.24 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-3790000000-98b2b4d927ad1042f83f

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Phenylpropanoic acids
Sub Class
Not Available
Direct Parent
Phenylpropanoic acids
Alternative Parents
Isoindolones / Isoindoles / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Lactams / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 3 more
Substituents
2-phenylpropanoic-acid / Isoindolone / Isoindoline / Isoindole / Isoindole or derivatives / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide / Carboxamide group / Lactam
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid, gamma-lactam, isoindoles (CHEBI:76162)

Drug created on May 27, 2014 13:29 / Updated on October 01, 2018 14:44