Basic information
- CAS
31842-01-0- Standard SMILES
CC(C(=O)O)c1ccc(N2Cc3ccccc3C2=O)cc1- InChIKey
RJMIEHBSYVWVIN-UHFFFAOYSA-N- Molecular formula
- C17H15NO3
- Average molar mass
- 281.3 g/mol
- Monoisotopic mass
- 281.10519334
Overview
Indoprofen is a monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-(1-oxo-1,3-dihydroisoindol-2-yl)phenyl group. Initially used as an anti-inflammatory and analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It has been subsequently found to increase production of the survival motor neuron protein. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic and an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor. It is a member of isoindoles, a monocarboxylic acid and a gamma-lactam. It is functionally related to a propionic acid.
Names & identifiers
- Preferred name
- Indoprofen
- IUPAC
- 2-[4-(3-oxo-1H-isoindol-2-yl)phenyl]propanoic acid
- English name
- alpha-Methyl-p-[1-oxo-2-isoindolinyl]-benzeneacetic acid
- Molecular formula
- C17H15NO3
- Molecular weight
- 281.31
Names & synonyms
indoprofen31842-01-0IsindoneReumofeneFlosinFlosintIndoprofeneIndoprofenoPraxisBor-indIndoprofenumK 4277
Show more names
k4277ReumofeAids025462
2-(4-(1-Carboxyethyl)phenyl)-1-isoindolinoneDTXSID5045831p-(1-Oxo-2-isoindolinyl)hydratropic acidCPE46ZU14NK-4277NSC-7570651-Oxo-2-(p-((alpha-methyl)carboxymethyl)phenyl)isoindoline4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)-alpha-methylbenzeneacetic acid
Database identifiers
- CAS
31842-01-0- PubChem CID
- 3718
- DTXSID
DTXSID5045831- ChEMBL
CHEMBL15870- ChEBI
CHEBI:76162- UNII
- CPE46ZU14N
- EC Number
- 250-833-0
- Nikkaji
- J19.918D
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 57.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 414
Experimental & physicochemical properties
Solubility>42.2 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsPharmaceuticals
Melting Point208-210
Collision Cross Section
166.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
166.4 Ų [M+H]+ [CCS Type: TW]
155.36 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 213 · 213-214°
- Boiling point
- 423.97 °C · 423.97°C (rough estimate)
- Density
- 1.1302 · 1.1302 (rough estimate)
- refractive index
- 1.45 · 1.4500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly, Sonicated)
- form
- Solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Benzeneacetic acid, 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-.alpha.-methyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- 3
- rtecs
- MU6645000
- ridadr
- UN 2811 6.1 / PGIII
- Toxicity
- LD50 in rats (mg/kg): 58.66 i.v.; 60.83 orally (Buttinoni)
- risk_code
- 25-40
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- T
- safety_code
- 22-36/37/39-45
- Hazard statements
- H301-H351
- Precautionary statements
- P201-P301+P310+P330
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
Biological Half-Life2.3 hours.
Metabolism/MetabolitesGlucuronidation.
MeSH Pharmacological ClassificationCompounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Absorption, Distribution and ExcretionRenal.
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesALPHA-METHYL-P-[1-OXO-2-ISOINDOLINYL]-BENZENEACETIC ACID is a non-steroidal anti-inflammatory agent used for treatment of pain and inflammation
Usesanalgesic, antiinflammatory
Upstream & downstream products
Upstream raw materials
Related reactions
10 records
Compound notes
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