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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H17N3O.C6H8O6
Molecular Weight 407.4177
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINOPHENAZONE ASCORBATE

SMILES

[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO.CN(C)C2=C(C)N(C)N(C2=O)C3=CC=CC=C3

InChI

InChIKey=ZPBURGJOLTWBJU-MGMRMFRLSA-N
InChI=1S/C13H17N3O.C6H8O6/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11;7-1-2(8)5-3(9)4(10)6(11)12-5/h5-9H,1-4H3;2,5,7-10H,1H2/t;2-,5+/m.0/s1

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

Molecular Formula C6H8O6
Molecular Weight 176.1241
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Drug-induced anaphylaxis, convulsions, deafness, and extrapyramidal symptoms.
1977 Mar 12
Effects of nonvolatile agents on oxygen demand and energy status in isolated hepatocytes.
1988 Oct
[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
Identification and significance of phenazone drugs and their metabolites in ground- and drinking water.
2002 Nov
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
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
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:05:10 GMT 2023
Edited
by admin
on Sat Dec 16 08:05:10 GMT 2023
Record UNII
G46D7HK10C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMINOPHENAZONE ASCORBATE
Common Name English
ANTIPYRINE, 4-(DIMETHYLAMINO)-, L-ASCORBATE
Common Name English
L-ASCORBIC ACID, COMPD. WITH 4-(DIMETHYLAMINO)-1,2-DIHYDRO-1,5-DIMETHYL-2-PHENYL-3H-PYRAZOL-3-ONE
Common Name English
VADITON
Brand Name English
AMINOPYRINE ASCORBATE
Common Name English
L-ASCORBIC ACID, COMPD. WITH 4-(DIMETHYLAMINO)ANTIPYRINE
Common Name English
3H-PYRAZOL-3-ONE, 4-(DIMETHYLAMINO)-1,2-DIHYDRO-1,5-DIMETHYL-2-PHENYL-, COMPD. WITH L-ASCORBIC ACID
Common Name English
Code System Code Type Description
FDA UNII
G46D7HK10C
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY
CAS
23635-43-0
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY
PUBCHEM
72710703
Created by admin on Sat Dec 16 08:05:10 GMT 2023 , Edited by admin on Sat Dec 16 08:05:10 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY