U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of AMINOPHENAZONE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.8 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Pyramidon

Approved Use

Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Palliative
Pyramidon

Approved Use

Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Palliative
Pyramidon

Approved Use

Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Palliative
Pyramidon

Approved Use

Aminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.7 μg/mL
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
17.4 μg/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.3 h
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
2.6 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
AMINOPHENAZONE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse 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
Co-administed with::
allobarbitone(30 mg; 1-2 tablets once or twice per day for 18 days)
Sources:
unhealthy, 27 years
n = 1
Health Status: unhealthy
Condition: pain
Age Group: 27 years
Sex: F
Population Size: 1
Sources:
Other AEs: Agranulocytosis...
Other AEs:
Agranulocytosis
Sources:
10 % 1 times / day single, topical
Studied dose
Dose: 10 %, 1 times / day
Route: topical
Route: single
Dose: 10 %, 1 times / day
Sources:
healthy, 28 years
n = 1
Health Status: healthy
Age Group: 28 years
Sex: F
Population Size: 1
Sources:
Other AEs: Contact urticaria...
Other AEs:
Contact urticaria
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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:
220 mg 2 times / day multiple, rectal
Recommended
Dose: 220 mg, 2 times / day
Route: rectal
Route: multiple
Dose: 220 mg, 2 times / day
Co-administed with::
codeine(5 mg; 2 per day)
diallymal(30 mg; 2 per day)
Sources:
unhealthy, mean age 6.4 years
n = 43
Health Status: unhealthy
Condition: pain
Age Group: mean age 6.4 years
Sex: M+F
Population Size: 43
Sources:
Other AEs: Vomiting...
Other AEs:
Vomiting (5.5%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Co-administed with::
allobarbitone(30 mg; 1-2 tablets once or twice per day for 18 days)
Sources:
unhealthy, 27 years
n = 1
Health Status: unhealthy
Condition: pain
Age Group: 27 years
Sex: F
Population Size: 1
Sources:
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:
healthy, 28 years
n = 1
Health Status: healthy
Age Group: 28 years
Sex: F
Population Size: 1
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
barbital(114 mg; 2 per day during 2.5 days)
aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days)
Sources:
unhealthy, mean age 24.3 years
n = 84
Health Status: unhealthy
Condition: pain
Age Group: mean age 24.3 years
Sex: M+F
Population Size: 84
Sources:
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
Co-administed with::
codeine(5 mg; 2 per day)
diallymal(30 mg; 2 per day)
Sources:
unhealthy, mean age 6.4 years
n = 43
Health Status: unhealthy
Condition: pain
Age Group: mean age 6.4 years
Sex: M+F
Population Size: 43
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
[Bilateral renal cortical necrosis following pyrazolone treatment].
1967 Jun 9
Short-term study of the effect of phenacetin, phenazone and amidopyrine on the rat kidney.
1968 Jan
Tumor induction in rats by feeding aminopyrine or oxytetracycline with nitrite.
1975 Aug 15
Drug-induced anaphylaxis, convulsions, deafness, and extrapyramidal symptoms.
1977 Mar 12
Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates.
1979 May
Toxic etiology of aplastic anemia. The Cooperative Study Group for Aplastic and Refractory Anemias.
1984 Oct-Dec
Effects of nonvolatile agents on oxygen demand and energy status in isolated hepatocytes.
1988 Oct
Mechanism of peroxidative activation of the bladder carcinogen 2-amino-4-(5-nitro-2-furyl)-thiazole (ANFT): comparison with benzidine.
1990 Nov
[Amidazophen. Yes or no?].
1995 Sep 24
Role of caffeine in combined analgesic drugs from the point of view of experimental pharmacology.
1997 Aug
Breath tests: concepts, applications and limitations.
1997 Aug
Toxic epidermal necrolysis in a patient with severe aplastic anemia treated with cyclosporin A and G-CSF.
2001
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
The influence of interferon alpha on the rat liver injured by chronic administration of carbon tetrachloride.
2002
Studies on new cyclic imides obtained from aminophenazone with analgesic properties. Potent effects of a 3,4-dichloromaleimide derivative.
2002
Identification and significance of phenazone drugs and their metabolites in ground- and drinking water.
2002 Nov
IgE-mediated immediate-type hypersensitivity to the pyrazolone drug propyphenazone.
2003 Apr
Determination of polar drug residues in sewage and surface water applying liquid chromatography-tandem mass spectrometry.
2004 Nov 15
Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention.
2005 Dec
Oxidation of pharmaceuticals during water treatment with chlorine dioxide.
2005 Sep
[Detection of phenol by means of 4-aminophenazone according to Emerson].
2006 Sep
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.
2007 Feb 26
Investigation of the behavior and metabolism of pharmaceutical residues during purification of contaminated ground water used for drinking water supply.
2007 Nov
Efficient use of the iron ortho-nitrophenylporphyrin chloride to mimic biological oxidations of dimethylaminoantipyrine.
2007 Oct
Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury.
2008
A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women.
2008 Feb-Mar
Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters.
2008 Jan
Scavenging activity of aminoantipyrines against hydroxyl radical.
2010 Jun
Synthesis and anti-bacterial activities of some novel Schiff bases derived from aminophenazone.
2010 Oct 8
The study of aminophenazone radical cation and its interaction with some antioxidants.
2010 Oct-Dec
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 Jul 3
Patents

Sample Use Guides

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.
Name Type Language
AMINOPHENAZONE
INN   MART.   WHO-DD  
INN  
Official Name English
AMINOPYRINE
HSDB   JAN   MI  
Common 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
WHO-ATC N02BB03
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
WHO-VATC QN02BB53
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
WHO-ATC N02BB53
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
NCI_THESAURUS C257
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
WHO-VATC QN02BB03
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
WHO-VATC QN02BB73
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
WHO-ATC N02BB73
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
Code System Code Type Description
HSDB
2135
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
SMS_ID
100000092139
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
MESH
D000632
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
WIKIPEDIA
AMINOPHENAZONE
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
INN
375
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
RXCUI
695
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C76792
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-365-8
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
DRUG BANK
DB01424
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
CHEBI
160246
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
PUBCHEM
6009
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
EVMPD
SUB05442MIG
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID7020504
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
DRUG CENTRAL
171
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
FDA UNII
01704YP3MO
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
CAS
58-15-1
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
NSC
4993
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY
MERCK INDEX
m1740
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL288470
Created by admin on Sat Dec 16 17:29:41 UTC 2023 , Edited by admin on Sat Dec 16 17:29:41 UTC 2023
PRIMARY