Aminophenazone
- 4 -dimethylamino-1 ,5-dimethyl -2-phenyl -1 ,2- dihydro -3H -pyrazol- 3-one ( IUPAC)
- Dimethylaminophenyldimethylpyrazolon
- 4- dimethylaminoantipyrine
- Aminopyrine
- 2,3- dimethyl-4- dimethylamino -1-phenyl -5-pyrazolone
- Dimethylaminophenazon
- Pyramidon
N02BB03
Light-sensitive, flammable, white to off- white crystalline powder or colorless crystals
Fixed
107 to 108.5 ° C
- Slightly soluble in water
- Slightly soluble in ethanol 96 %
Risk
Template: Infobox chemical / molecular formula search available
Aminophenazone is a chemical compound from the group of nitrogen heterocycles and pyrazolone derivatives. It thus consists of ( the well-known in the fever and pain ) pyrazolone skeleton having an amino group in the 4- position of the pyrazolone heterocycle.
History
Friedrich Ludwig Knorr pride and are considered the inventors of aminophenazone, which came in 1897 by Hoechst as Pyramidon ® on the market.
Production and representation
Aminophenazone can be obtained from phenazone by nitration and subsequent reduction.
Use
Aminophenazone is a pyrazolone ( pyrazolin- 3-one) with analgesic, anti-inflammatory and antipyretic properties ( ie is a non-opioid analgesic with over Phenazone three times more impact ), but has the risk of agranulocytosis. A breath test using 13C -labeled aminopyrine was for non-invasive measurement of the cytochrome P-450 activity is used in the liver. Aminophenazone as a further development of antipyrine may only veterinary use ( in early stages of septic Schockes in dogs and cats and in combination with phenylbutazone ) yet and will be replaced in combination products since 1977 by propyphenazone due to the carcinogenic metabolites dimethylnitrosamine.
Pharmacokinetics
Following oral administration of aminophenazone is rapidly absorbed. [T 2] It is a low plasma protein binding before. Demonstrated in rats was 30 minutes after the administration of an increased concentration in the nasal mucosa and in the liver [3 t]. [T 4] in the urine was detected 4 -acetylamino- 3- methyl-1- phenylpyrazolone. This suggests oxidative N -dealkylation by the MFO system [t 5] ( cytochrome P450 - containing monooxygenase or mixed function oxygenases ) in the liver and subsequent acetylation of the free primary amino group close. [T 1] An analogous mechanism in the metabolism the structurally very similar dipyrone metabolite 4 - methylaminophenazone observed after its absorption. The rate of metabolism by the cytochrome P450 system in rats depending on the time. [T 6] Renal is aminophenazone either unchanged glucoronidiert or excreted sulfated. [T 2] It is also reported on the excretion of Rubazonsäure, [t 7] which has a red coloration of the urine can cause ..