NAV

Indoprofen

Identification

Generic Name
Indoprofen
DrugBank Accession Number
DB08951
Background

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 Following reports of adverse reactions including reports of carcinogenicity in animal studies it was withdrawn from the market worldwide.

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 281.3059
Monoisotopic: 281.105193351
Chemical Formula
C17H15NO3
Synonyms
  • Indoprofen
  • indoprofeno
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPyruvate kinase PKM
inhibitor
Humans
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.

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirIndoprofen may decrease the excretion rate of Abacavir which could result in a higher serum level.
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 Aceclofenac is combined with Indoprofen.
AcemetacinThe risk or severity of adverse effects can be increased when Indoprofen is combined with Acemetacin.
Food Interactions
Not Available

Categories

ATC Codes
M01AE10 — Indoprofen
Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Isoindole
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid, gamma-lactam, isoindoles (CHEBI:76162)
Affected organisms
Not Available

Chemical Identifiers

UNII
CPE46ZU14N
CAS number
31842-01-0
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

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. [Article]
KEGG Drug
D04530
PubChem Compound
3718
PubChem Substance
310264916
ChemSpider
3587
BindingDB
50233673
ChEBI
76162
ChEMBL
CHEMBL15870
Wikipedia
Indoprofen

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-000i-3790000000-98b2b4d927ad1042f83f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-3790000000-98b2b4d927ad1042f83f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-0090000000-6b60321539129fdadb18
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0190000000-e8edfb1e1f2d623b733f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1090000000-4c343b7ed6e378b24728
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-1690000000-6d05b743383f82b53a00
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-8970000000-840435af72e153ab31c7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zgi-0910000000-cf3bfb3e2d0773adc92c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-160.39482
predicted
DeepCCS 1.0 (2019)
[M+H]+162.75282
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.84596
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Pyruvate kinase PKM
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Pyruvate kinase activity
Specific Function
Glycolytic enzyme that catalyzes the transfer of a phosphoryl group from phosphoenolpyruvate (PEP) to ADP, generating ATP. Stimulates POU5F1-mediated transcriptional activation. Plays a general rol...
Gene Name
PKM
Uniprot ID
P14618
Uniprot Name
Pyruvate kinase PKM
Molecular Weight
57936.38 Da
References
  1. Ye X, Sun Y, Xu Y, Chen Z, Lu S: Integrated In Silico-In Vitro Discovery of Lung Cancer-related Tumor Pyruvate Kinase M2 (PKM2) Inhibitors. Med Chem. 2016;12(7):613-620. doi: 10.2174/1573406412666160307151535. [Article]

Drug created at May 27, 2014 19:29 / Updated at May 04, 2022 04:18