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Details

Stereochemistry ACHIRAL
Molecular Formula C13H17N3O.C9H7NO4S
Molecular Weight 456.515
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMINOPHENAZONE 8-HYDROXYQUINOLIN-7-SULFONATE

SMILES

OC1=C2N=CC=CC2=CC=C1S(O)(=O)=O.CN(C)C3=C(C)N(C)N(C3=O)C4=CC=CC=C4

InChI

InChIKey=QKTQVOHDBURFQG-UHFFFAOYSA-N
InChI=1S/C13H17N3O.C9H7NO4S/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11;11-9-7(15(12,13)14)4-3-6-2-1-5-10-8(6)9/h5-9H,1-4H3;1-5,11H,(H,12,13,14)

HIDE SMILES / InChI

Molecular Formula C9H7NO4S
Molecular Weight 225.221
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H17N3O
Molecular Weight 231.2936
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
3.8 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Pyramidon
Palliative
Pyramidon
Palliative
Pyramidon
Palliative
Pyramidon

Cmax

ValueDoseCo-administeredAnalytePopulation
17.4 μg/mL
600 mg single, oral
AMINOPHENAZONE plasma
Homo sapiens
2.7 μg/mL
250 mg single, oral
AMINOPHENAZONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.6 h
600 mg single, oral
AMINOPHENAZONE plasma
Homo sapiens
2.3 h
250 mg single, oral
AMINOPHENAZONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
85%
AMINOPHENAZONE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Drug as victim

PubMed

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
Record UNII
9FJ50DJA4M
Record Status Validated (UNII)
Record Version