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

Molecular Formula	C14H18N2O
Molecular Weight	230.3055
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25221653	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Headache 47 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8583	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 1983
Toothache 15 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8583	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 1983
Lumbago 8 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8583	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 1983
Nerve pain 1 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8583	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 1983
Fever 23 Sources: http://www.lareb.nl/Signalen/kwb_2004_2_sarid.aspx	Primary	Approved 8583	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 1983

C_max

Value	Dose	Co-administered	Analyte	Population
3252.083 μg/L EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-DSDX200818007.htm	220 mg single, oral dose: 220 mg route of administration: Oral experiment type: SINGLE co-administered: DIPHENHYDRAMINE	DIPHENHYDRAMINE	PROPYPHENAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3220 μg/L EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-DSDX200818007.htm	220 mg 3 times / day multiple, oral dose: 220 mg route of administration: Oral experiment type: MULTIPLE co-administered: DIPHENHYDRAMINE	DIPHENHYDRAMINE	PROPYPHENAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3320 μg/L EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-DSDX200818007.htm	220 mg 3 times / day steady-state, oral dose: 220 mg route of administration: Oral experiment type: STEADY-STATE co-administered: DIPHENHYDRAMINE	DIPHENHYDRAMINE	PROPYPHENAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
8055.037 μg × h/L EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-DSDX200818007.htm	220 mg single, oral dose: 220 mg route of administration: Oral experiment type: SINGLE co-administered: DIPHENHYDRAMINE	DIPHENHYDRAMINE	PROPYPHENAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
6522.007 μg × h/L EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-DSDX200818007.htm	220 mg 3 times / day multiple, oral dose: 220 mg route of administration: Oral experiment type: MULTIPLE co-administered: DIPHENHYDRAMINE	DIPHENHYDRAMINE	PROPYPHENAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.826 h EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-DSDX200818007.htm	220 mg single, oral dose: 220 mg route of administration: Oral experiment type: SINGLE co-administered: DIPHENHYDRAMINE	DIPHENHYDRAMINE	PROPYPHENAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.029 h EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-DSDX200818007.htm	220 mg 3 times / day multiple, oral dose: 220 mg route of administration: Oral experiment type: MULTIPLE co-administered: DIPHENHYDRAMINE	DIPHENHYDRAMINE	PROPYPHENAZONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
80% REVIEW https://link.springer.com/chapter/10.1007/978-3-319-33889-7_1			PROPYPHENAZONE unknown	Homo sapiens

Doses

Dose	Population	Adverse events
300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/	Other AEs: Tiredness, Dizziness... Other AEs: Tiredness (4 patients) Dizziness (1 pt) Feeling of relaxation (1 pt) Feeling of warmth (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/

AEs

AE	Significance	Dose	Population
Dizziness	1 pt	300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/
Feeling of relaxation	1 pt	300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/
Feeling of warmth	1 pt	300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/
Tiredness	4 patients	300 mg single, oral Highest studied dose Dose: 300 mg Route: oral Route: single Dose: 300 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3492378/

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
Drug-induced hepatitis with hepatic granuloma due to saridon.	2002	12522541
IgE-mediated immediate-type hypersensitivity to the pyrazolone drug propyphenazone.	2003 Apr	12704373
Determination of polar pharmaceuticals in sewage water of Greece by gas chromatography-mass spectrometry.	2003 Apr	12586139
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
Dissolution and assaying of multicomponent tablets by chemometric methods using computer-aided spectrophotometer.	2003 Jan 16	12527161
[Current aspects of the treatment of migraine].	2003 Jul-Aug	14618813
Optimization of the RP-HPLC method for multicomponent analgetic drug determination.	2003 Nov	14971306
Wavelet analysis for the multicomponent determination in a binary mixture of caffeine and propyphenazone in tablets.	2004 Apr	15081352
[Two cases of anaphylactic shock after metamizol given during postoperative recovery].	2004 Mar	15200191
[Propyphenazone. Pharmacology and use].	2004 Mar	15032249
Developmental effects of propyphenazone in analgesic and antipyretic combination with caffeine or paracetamol.	2004 May	15222401
Safety of the new selective cyclooxygenase type 2 inhibitors rofecoxib and celecoxib in patients with anaphylactoid reactions to nonsteroidal anti-inflammatory drugs.	2004 Oct	15521372
Pharmaceuticals in the river Elbe and its tributaries.	2004 Oct	15294435
Detection and identification of phenazone-type drugs and their microbial metabolites in ground and drinking water applying solid-phase extraction and gas chromatography with mass spectrometric detection.	2004 Oct 1	15508313
Transport of pharmaceutically active compounds in saturated laboratory columns.	2004 Sep-Oct	15457799
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
Treatment of a landfill leachate containing compounds of pharmaceutical origin.	2008	18725727
Rejection of pharmaceuticals in nanofiltration and reverse osmosis membrane drinking water treatment.	2008 Aug	18656225
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
Evaluation of pharmaceuticals and personal care products as water-soluble molecular markers of sewage.	2008 Sep 1	18800500
Fate and distribution of pharmaceuticals in wastewater and sewage sludge of the conventional activated sludge (CAS) and advanced membrane bioreactor (MBR) treatment.	2009 Feb	19091371
Synaptopodin regulates plasticity of dendritic spines in hippocampal neurons.	2009 Jan 28	19176811
Quantification of 4-methylaminoantipyrine, the active metabolite of dipyrone, in human plasma.	2009 May	21083168
Acute myocardial infarction and Kounis syndrome.	2009 May 15	18378025
The characteristics of enriched nitrifier culture in the degradation of selected pharmaceutically active compounds.	2009 Nov 15	19615816
A case of linear immunoglobulin A bullous dermatosis in a patient exposed to sun and an analgesic.	2009 Sep	19843488
The role of organic matter in the removal of emerging trace organic chemicals during managed aquifer recharge.	2010 Jan	19748650
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
Diclofenac hypersensitivity: antibody responses to the parent drug and relevant metabolites.	2010 Oct 28	21060839

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:12 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:12 GMT 2025`
Record UNII	OED8FV75PY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROPYPHENAZONE

Official Name

English

YOSHIPYRIN

Preferred 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

Classification Tree Code System Code

WHO-VATC

QN02BB74