Chemical Properties
White Powder
History
Antipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.
Uses
Antipyrine has been used for immunoblotting. It has also been used as an internal reference marker for studying the transport characteristics of platinum-containing drug, cisplatin in the human placenta in vitro.
Uses
Analgesic; used to test hepatic drug-metabolizing activity.
Definition
ChEBI: A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at C-1 and C-5 and with a phenyl group at N-2.
Preparation
Antipyrine (1) was prepared from the reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with methyl iodide in methanol or in acetonitrile containing sodium bicarbonate in water in 58% yield. The reaction of 1-methyl-2-phenylhydrazine (2) with methyl 3-oxobutanoate (3) in acetonitrile gave 1 and pyrazolone 4 . Krohn has been reported the synthesis of 1 from the reaction of 5 with dimethyl sulfate in 71% yield. The reaction of pyrazolone 6 with methanol in the presence of triphenylphosphine afforded 1 (14%) and pyrazole 7 (53%). The same reaction was reported by Pegurier et al by heating the reactants in methanol containing calcium monoxide. Knorr early reported also, the synthesis of antipyrine from heating of 1-phenyl-5-ethoxy-3- methylpyrazole (8) with methyl iodide in methanol.
Brand name
Aerol;Antigestin;Asthma dellipsoids;Aurafair;Auralgicin;Auraltone;Bajumol;Breezeazy;Calmasmin;Cetussan;Codalgin;Crema antisolar evanescente;Doleron novum;Dolo-med-much;Dol-stop;Kalopsis;Lanceotic;Lavylgan;Mig-antos;Migranin;Natt-lunedon;Neo-felsol;Orecil;Otipyrin;Otosan-sulfan;Otothricinol;Palacaine;Pasta antisola;Pomada heridas;Prednefrin;Prefrin liquifilm;Prefrin z;Priatan;Prophyllen;Remolmed;Salicopil;Sedaural;Sedonan;Shhe 21;Spalt n;Tympagesic;Visublefarite.
World Health Organization (WHO)
Phenazone is a pyrazolone derivative chemically related to
aminophenazone. Some regulatory authorities have imposed restrictions on its use
on these grounds. However, a recent international study showed no statisticallybased
evidence of an association with agranulocytosis or aplastic anaemia. Nor
does it share with aminophenazone the propensity to produce potentially
carcinogenic nitrosamines.
General Description
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Biochem/physiol Actions
Antipyrine also referred to as phenazone or phenazonum is an anti-inflammatory agent that possesses analgesic, antipyretic and platelet-inhibitory actions.
Purification Methods
Antipyrine crystallises from EtOH/water mixture, *benzene, *benzene/pet ether or hot water (charcoal), and the crystals are dried under a vacuum. [Beilstein 24 H 27, 24 III/IV 75.]
