AMINOPHENAZONE

US Previously Marketed

First marketed in 1897

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H17N3O
Molecular Weight	231.2936
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RMMXTBMQSGEXHJ-UHFFFAOYSA-N

InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3

HIDE SMILES / InChI

Molecular Formula	C13H17N3O
Molecular Weight	231.2936
Charge	0
Count

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

Description
Sources: http://noillen.bitballoon.com/medicine2/amidopyrine-instruct261 | Vaz, R.J. & Klabunde, T. (2008) Antitargets: Prediction and Prevention of Drug Side Effects, page 5, retrieved from: https://books.google.ru/books?id=oSnSk1kv0dAC | (2004) Consolidated List of Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments: Pharmaceuticals, page 18, retrieved from: https://books.google.ru/books?id=leVCukUgNlsC | Suchy, F.J. et al. (2007) Liver Disease in Children, page 107, retrieved from: https://books.google.ru/books?id=rGxPASmZWesC

Aminophenazone is a phenyl-pyrazolone derivative with potent analgesic and antipyretic properties. Aminophenazone has been used as salt or complexes, including topically as the salicylate. It was recommended for the treatment of a fever, neuralgia, myositis, acute rheumatism, arthritis, chorea. In 1999 the FDA suspended aminophenazone. The drug caused agranulocytosis. Some of the cases of agranulocytosis were fatal. Another reason for suspending this drug from the market was its ability to react with nitrite-containing food, thus forming carcinogenic nitrosamines. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2095157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2498559	Inhibitor 8504		3.8 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Myositis 7 Sources: http://noillen.bitballoon.com/nutritional-suppleme5/	Palliative	Withdrawn	Pyramidon Approved Use Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Arthritis 87 Sources: http://noillen.bitballoon.com/medicine2/amidopyrine-instruct261	Palliative	Withdrawn	Pyramidon Approved Use Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Rheumatism 10 Sources: http://noillen.bitballoon.com/medicine2/amidopyrine-instruct261	Palliative	Withdrawn	Pyramidon Approved Use Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Neuralgia 12 Sources: http://noillen.bitballoon.com/medicine2/amidopyrine-instruct261	Palliative	Withdrawn	Pyramidon Approved Use Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.

C_max

Value	Dose	Co-administered	Analyte	Population
17.4 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/7002187/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		AMINOPHENAZONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.7 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/7002187/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		AMINOPHENAZONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.6 h REVIEW https://pubmed.ncbi.nlm.nih.gov/7002187/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		AMINOPHENAZONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
2.3 h REVIEW https://pubmed.ncbi.nlm.nih.gov/7002187/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		AMINOPHENAZONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
85% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15437290/			AMINOPHENAZONE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
220 mg 1 times / day multiple, oral Recommended Dose: 220 mg, 1 times / day Route: oral Route: multiple Dose: 220 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/	unhealthy, 27 years Health Status: unhealthy Age Group: 27 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/	Other AEs: Agranulocytosis... Other AEs: Agranulocytosis Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/
10 % 1 times / day single, topical Studied dose Dose: 10 %, 1 times / day Route: topical Route: single Dose: 10 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/	healthy, 28 years Health Status: healthy Age Group: 28 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/	Other AEs: Contact urticaria... Other AEs: Contact urticaria Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/
286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	Other AEs: Tiredness, Nausea... Other AEs: Tiredness (13.1%) Nausea (10.7%) Headache (1.2%) Vomiting (1.2%) Mental confusion (5.9%) Palpitation (1.2%) Faintness (1.2%) Loss of memory (1.2%) Urticaria (1.2%) Vertigo (1.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
220 mg 2 times / day multiple, rectal Recommended Dose: 220 mg, 2 times / day Route: rectal Route: multiple Dose: 220 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/	unhealthy, mean age 6.4 years Health Status: unhealthy Age Group: mean age 6.4 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/	Other AEs: Vomiting... Other AEs: Vomiting (5.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/

AEs

AE	Significance	Dose	Population
Agranulocytosis		220 mg 1 times / day multiple, oral Recommended Dose: 220 mg, 1 times / day Route: oral Route: multiple Dose: 220 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/	unhealthy, 27 years Health Status: unhealthy Age Group: 27 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6105412/
Contact urticaria		10 % 1 times / day single, topical Studied dose Dose: 10 %, 1 times / day Route: topical Route: single Dose: 10 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/	healthy, 28 years Health Status: healthy Age Group: 28 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6627934/
Faintness	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Headache	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Loss of memory	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Palpitation	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Urticaria	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Vertigo	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Vomiting	1.2%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Nausea	10.7%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Tiredness	13.1%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Mental confusion	5.9%	286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/	unhealthy, mean age 24.3 years Health Status: unhealthy Age Group: mean age 24.3 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3125269/
Vomiting	5.5%	220 mg 2 times / day multiple, rectal Recommended Dose: 220 mg, 2 times / day Route: rectal Route: multiple Dose: 220 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/	unhealthy, mean age 6.4 years Health Status: unhealthy Age Group: mean age 6.4 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/4589282/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C18 149 CYP2C19 1119 CYP2E1 729

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2C18 149	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/12124312/ \| https://pubmed.ncbi.nlm.nih.gov/28057172/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/28057172/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/28057172/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10784435/ \| https://pubmed.ncbi.nlm.nih.gov/19515014/ \| https://pubmed.ncbi.nlm.nih.gov/10199594/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:160246	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:160246
ChemicalBook	CB1476086	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1476086
eMolecules	537453	https://www.emolecules.com/cgi-bin/more?vid=537453
MolPort	MolPort-001-783-069	https://www.molport.com/shop/molecule-link/MolPort-001-783-069
Selleck Chemicals	amidopyrine	http://www.selleckchem.com/products/amidopyrine.html
ZINC	ZINC000000057115	http://zinc15.docking.org/substances/ZINC000000057115

PubMed

Title	Date	PubMed
Development of a cell-based assay system considering drug metabolism and immune- and inflammatory-related factors for the risk assessment of drug-induced liver injury.	2014-07-03	24747151
The study of aminophenazone radical cation and its interaction with some antioxidants.	2011-04-19	21495460
Synthesis and anti-bacterial activities of some novel Schiff bases derived from aminophenazone.	2010-10-08	20938399
Scavenging activity of aminoantipyrines against hydroxyl radical.	2010-06	20172632
A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women.	2008-09-27	18818187
Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters.	2008-01	17692886
Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury.	2008	19040780
Investigation of the behavior and metabolism of pharmaceutical residues during purification of contaminated ground water used for drinking water supply.	2007-11	17662339
Efficient use of the iron ortho-nitrophenylporphyrin chloride to mimic biological oxidations of dimethylaminoantipyrine.	2007-10	17937780
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.	2007-02-26	17324258
[Detection of phenol by means of 4-aminophenazone according to Emerson].	2006-09	17020161
Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention.	2005-12	16141368
Oxidation of pharmaceuticals during water treatment with chlorine dioxide.	2005-09	16061268
Determination of polar drug residues in sewage and surface water applying liquid chromatography-tandem mass spectrometry.	2004-11-15	15538775
IgE-mediated immediate-type hypersensitivity to the pyrazolone drug propyphenazone.	2003-04	12704373
Identification and significance of phenazone drugs and their metabolites in ground- and drinking water.	2002-11	12430641
The influence of interferon alpha on the rat liver injured by chronic administration of carbon tetrachloride.	2002	12898905
Studies on new cyclic imides obtained from aminophenazone with analgesic properties. Potent effects of a 3,4-dichloromaleimide derivative.	2002	12109046
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001-11	11792017
Toxic epidermal necrolysis in a patient with severe aplastic anemia treated with cyclosporin A and G-CSF.	2001	11321886
Role of caffeine in combined analgesic drugs from the point of view of experimental pharmacology.	1997-08	9296278
Breath tests: concepts, applications and limitations.	1997-08	9266210
[Amidazophen. Yes or no?].	1995-09-24	7566947
Mechanism of peroxidative activation of the bladder carcinogen 2-amino-4-(5-nitro-2-furyl)-thiazole (ANFT): comparison with benzidine.	1990-11	2121382
Effects of nonvolatile agents on oxygen demand and energy status in isolated hepatocytes.	1988-10	3421495
Toxic etiology of aplastic anemia. The Cooperative Study Group for Aplastic and Refractory Anemias.	1984-10-01	6523314
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.	1979-05	458805
Drug-induced anaphylaxis, convulsions, deafness, and extrapyramidal symptoms.	1977-03-12	65671
Tumor induction in rats by feeding aminopyrine or oxytetracycline with nitrite.	1975-08-15	168160
Short-term study of the effect of phenacetin, phenazone and amidopyrine on the rat kidney.	1968-01	5640170
[Bilateral renal cortical necrosis following pyrazolone treatment].	1967-06-09	4225848

Patents

Sample Use Guides

In Vivo Use Guide

250-300 mg 3-4 times a day

Route of Administration: Oral

In Vitro Use Guide

Aminophenazone inhibits rat gastric mucosal 6-keto-prostaglandin F1 alpha production with IC50 3.8x10(-3) M.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:13:21 GMT 2025` Edited by `admin` on `Wed Apr 02 09:13:21 GMT 2025`
Record UNII	01704YP3MO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMINOPYRINE

Preferred Name

English

AMINOPHENAZONE

Official Name

English

aminophenazone [INN]

Common Name

English

AMINOPHENAZONE [MART.]

Common Name

English

Aminophenazone [WHO-DD]

Common Name

English

4-DIMETHYLAMINOANTIPYRINE

Common Name

English

AMINOPYRINE [MI]

Common Name

English

AMINOPYRINE [JAN]

Common Name

English

MAMALLET A

Common Name

English

AMIDOPYRINE

Common Name

English

AMIDOPYRAZOLINE

Common Name

English

FEBRON

Brand Name

English

3H-PYRAZOL-3-ONE, 4-(DIMETHYLAMINO)-1,2-DIHYDRO-1,5-DIMETHYL-2-PHENYL-

Systematic Name

English

4-DIMETHYLAMINO-1,5-DIMETHYL-2-PHENYL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE

Systematic Name

English

NSC-4993

Code

English

DEREUMA

Brand Name

English

ITAMIDONE

Brand Name

English

BRUFANEUXOL

Common Name

English

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

Systematic Name

English

METAMIZOLE SODIUM MONOHYDRATE IMPURITY D [EP IMPURITY]

Common Name

English

AMIDAZOPHENE

Common Name

English

AMINOPYRINE [HSDB]

Common Name

English

NETSUSARIN

Brand Name

English

Classification Tree Code System Code

CFR

21 CFR 216.24