PROPYPHENAZONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H18N2O
Molecular Weight	230.3055
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C1=C(C)N(C)N(C1=O)C2=CC=CC=C2

InChI

InChIKey=PXWLVJLKJGVOKE-UHFFFAOYSA-N

InChI=1S/C14H18N2O/c1-10(2)13-11(3)15(4)16(14(13)17)12-8-6-5-7-9-12/h5-10H,1-4H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25221653
Curator's Comment: description was created based on several sources, including https://www.medchemexpress.com/Propyphenazone.html?gclid=CKPT7oP5jM8CFUKeGwodv10NsQ

Propyphenazone is a pyrazolone derivative with anti-inflammatory, analgesic and antipyretic activity. The coupling of propyphenazone with other widely used acidic NSAIDs such as ketoprofen, ibuprofen, and diclofenac produced mutual prodrugs with synergistic analgesic effects. It was introduced for the treatment of different types of pain and fever and rheumatic disorders. Propyphenazone structurally relates to aminophenazone it has been associated with severe blood dyscrasias.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25221653	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Headache 47 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8429	saridon Approved Use It is indicated for: headache, toothache, nerve pain , lumbago, muscular pain, menstrual pain and fever and pain with influenza and viral rhinitis; fever and pain after vaccination Launch Date 4.11782414E11
Toothache 15 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8429	saridon Approved Use It is indicated for: headache, toothache, nerve pain , lumbago, muscular pain, menstrual pain and fever and pain with influenza and viral rhinitis; fever and pain after vaccination Launch Date 4.11782414E11
Lumbago 8 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8429	saridon Approved Use It is indicated for: headache, toothache, nerve pain , lumbago, muscular pain, menstrual pain and fever and pain with influenza and viral rhinitis; fever and pain after vaccination Launch Date 4.11782414E11
Nerve pain 1 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8429	saridon Approved Use It is indicated for: headache, toothache, nerve pain , lumbago, muscular pain, menstrual pain and fever and pain with influenza and viral rhinitis; fever and pain after vaccination Launch Date 4.11782414E11
Fever 23 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8429	saridon Approved Use It is indicated for: headache, toothache, nerve pain , lumbago, muscular pain, menstrual pain and fever and pain with influenza and viral rhinitis; fever and pain after vaccination Launch Date 4.11782414E11

PubMed

Title	Date	PubMed
Diagnosis of antibody-mediated drug allergy. Pyrazolinone and pyrazolidinedione cross-reactivity relationships.	1987 Nov	3425858
Autoimmune haemolytic anaemia induced by propyphenazone.	1998	9852417
Derivative ratio spectra-zero crossing spectrophotometry and LC method applied to the quantitative determination of paracetamol, propyphenazone and caffeine in ternary mixtures.	2001 Dec	11600288
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Drug-induced hepatitis with hepatic granuloma due to saridon.	2002	12522541
The onset of action and the analgesic efficacy of Saridon (a propyphenazone/paracetamol/ caffeine combination) in comparison with paracetamol, ibuprofen, aspirin and placebo (pooled statistical analysis).	2002	11999141
Advanced fibre optical scanning in thin-layer chromatography for drug identification.	2002 May 25	12016011
IgE-mediated immediate-type hypersensitivity to the pyrazolone drug propyphenazone.	2003 Apr	12704373
Effects of anti-inflammatory drugs on convulsant activity of quinolones: a comparative study of drug interaction between quinolones and anti-inflammatory drugs.	2003 Dec	14691652
[Current aspects of the treatment of migraine].	2003 Jul-Aug	14618813
Drug-induced anaphylaxis : case/non-case study based on an italian pharmacovigilance database.	2005	15924506
[Abuse pattern of analgesics in chronic daily headache: a study in the general population].	2005 Dec	16527179
Dipyrone and aminopyrine are effective scavengers of reactive nitrogen species.	2006	16805969
Long-term comparison of trace organics removal performances between conventional and membrane activated sludge processes.	2006 Dec	17243248
Mobility of pharmaceuticals carbamazepine, diclofenac, ibuprofen, and propyphenazone in miscible-displacement experiments.	2006 Feb 1	16343689
Inhibition of human neutrophil oxidative burst by pyrazolone derivatives.	2006 Feb 15	16458194
Celosomy is associated with prenatal exposure to cyclooxygenase inhibitors.	2006 Mar	16460959
Quantitative structure-pharmacokinetic relationships for drug clearance by using statistical learning methods.	2006 Mar	16290201
Pharmaceutical chemicals and endocrine disrupters in municipal wastewater in Tokyo and their removal during activated sludge treatment.	2006 Oct	16938339
Analysis of pharmaceuticals in wastewater and removal using a membrane bioreactor.	2007 Feb	17115140
Development of a multicommuted flow-through optosensor for the determination of a ternary pharmaceutical mixture.	2007 Jan 17	16978822
Determination of the analgesic components of Spasmomigraine tablet by liquid chromatography with ultraviolet detection.	2007 Jan-Feb	17373440
Development and validation of chemometrics-assisted spectrophotometry and liquid chromatography methods for the simultaneous determination of the active ingredients in two multicomponent mixtures containing chlorpheniramine maleate and phenylpropanolamine hydrochloride.	2007 Jul-Aug	17760333
Simultaneous determination of paracetamol, caffeine and propyphenazone in ternary mixtures by micellar electrokinetic capillary chromatography.	2007 Mar 1	17046340
Investigation of the behavior and metabolism of pharmaceutical residues during purification of contaminated ground water used for drinking water supply.	2007 Nov	17662339
Removal of selected pharmaceuticals and personal care products (PPCPs) and endocrine-disrupting chemicals (EDCs) during sand filtration and ozonation at a municipal sewage treatment plant.	2007 Nov	17632207
Removal of selected pharmaceuticals by chlorination, coagulation-sedimentation and powdered activated carbon treatment.	2008	18824814
Determination of caffeine and associated compounds in food, beverages, natural products, pharmaceuticals, and cosmetics by micellar electrokinetic capillary chromatography.	2008 Feb	18366873
Comprehensive screening and quantification of veterinary drugs in milk using UPLC-ToF-MS.	2008 Jul	18491081
Effects of propyphenazone and other non-steroidal anti-inflammatory agents on the synthetic and endogenous androgenic anabolic steroids urinary excretion and/or instrumental detection.	2010 Jan 4	19951758
VUV photon-induced ionization/dissociation of antipyrine and propyphenazone: mass spectrometric and theoretical insights.	2010 Jul	20623486
Two-column sequential injection chromatography--new approach for fast and effective analysis and its comparison with gradient elution chromatography.	2010 May 23	20457303

Patents

Sample Use Guides

In Vivo Use Guide

single oral doses of 150 and 300 mg

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

PROPYPHENAZONE

Official Name

English

ISOPROPYLANTIPYRINE [JAN]

Common Name

English

propyphenazone [INN]

Common Name

English

ISOPROPYLANTIPYRINE

Common Name

English

4-ISOPROPYL-2,3-DIMETHYL-1-PHENYL-3-PYRAZOLIN-5-ONE

Systematic Name

English

PROPYPHENAZONE [MI]

Common Name

English

Propyphenazone [WHO-DD]

Common Name

English

ISOPROPYLPHENAZONE

Systematic Name

English

PROPYPHENAZONE [EP MONOGRAPH]

Common Name

English

PROPYPHENAZONE [MART.]

Common Name

English

YOSHIPYRIN

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QN02BB74