アンチピリン

解説アンチピリンは，アミノピリンよりはいくらか弱いながらも比較的に強い解熱鎮痛作用をもち，19世紀の終りころからわりあいに近ごろまで広く使用されてきた薬物。アミノピリンと同じく，ピラゾロン誘導体，いわゆる〈ピリン系〉薬剤で，現在ではその使用は急速に低下しアスピリンのほうに比重が移っている。分子の化学構造からみてアミノピリンとよく似ているが，アミノピリンでみられるような致命的な副作用，すなわち無顆粒球症が誘発される危険はいちおうないものとされており，またアスピリンでみられるような消化性潰瘍の副作用もないが，ピリン疹の名で知られる皮膚の発疹をおこすことが類似の薬物のなかでは最も多い。株式会社平凡社 世界大百科事典 第２版について 情報

用途アンチピリン（国際一般名?英国一般名：Phenazone、米国一般名：Antipyrine）とはピラゾロン誘導体であるサリチル酸様鎮痛解熱薬の一つである。頭痛、リウマチ、月経痛などに用いられる。体温調節中枢に作用し、皮膚血管を拡張することにより熱の放散を活発にする。 日本薬局方「ミグレニン」の主成分である。鎮痛、解熱に用いられる。疾患や他の薬剤が肝臓の代謝酵素に及ぼす影響を調べる際にも使われる。

用途ピラゾロン系化合物です。プ ロスタグランジン生合成阻害作用を示しま す。

用途薬理研究用。

来歴Antipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.

使用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. Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. It is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

一般的な説明Antipyrine is an antipyretic agent used for the symptomatic treatment of acute otitis media, most commonly in combination with benzocaine. One of the earliest widely used analgesics and antipyretics, antipyrine was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen.

製造方法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.

純化方法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.]

定義ChEBI: Antipyrine is a pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2. It has a role as a non-narcotic analgesic, an antipyretic, a non-steroidal anti-inflammatory drug, a cyclooxygenase 3 inhibitor, a xenobiotic and an environmental contaminant.