Propyphenazone Explained

Propyphenazone (known as isopropylantipyrine in Japan)^[1] is a derivative of phenazone^[2] with similar analgesic and antipyretic effects. Originally patented in 1931,^[3] propyphenazone is marketed as a combination formulation with paracetamol and caffeine for treatment of primary headache disorder.^[4]

Synthesis

Ethyl 2-isopropylacetoacetate (1) and phenylhydrazine (2) are combined to form the pyrazolone ring in the intermediate (3), which is alkylated with methyl iodide to yield propyphenazone.^{[5] [6]}

Serious adverse events

Case reports have described acute inferior-wall myocardial infarctions characterized by low atrial rhythms (Kounis syndrome) secondary to propyphenazone use.^[7]

Banned

• Sri Lanka^[8]
• Malaysia
• Thailand

See also

• Propyphenazone/paracetamol/caffeine

Notes and References

1. Web site: Isopropylantipyrine. Drugs.com. 8 March 2018.
2. Göres E, Kossowicz J, Schneider HG . [Propyphenazone. Pharmacology and use] . German . Medizinische Monatsschrift für Pharmazeuten . 27 . 3 . 72–6 . March 2004 . 15032249 . Propyphenazone. Pharmacology and use .
3. Book: Fischer J, Ganellin CR . Analogue-based Drug Discovery . 2006 . John Wiley & Sons . 9783527607495 . 530 . en.
4. News: SC exempts painkiller Saridon from the banned list in India. February 21, 2019. The Economic Times.
5. 10.1248/yakushi1881.57.11_953 . free . Synthese verschiedener Pyrazolonderivate . 1937 . Sawa . Yoshiro . Yakugaku Zasshi . 57 . 11 . 953–962 . DE.
6. Web site: Propyphenazone . Pharmaceutical Substances . Thieme . 2024-07-17.
7. Akyel A, Alsancak Y, Yayla Ç, Sahinarslan A, Özdemir M . Acute inferior myocardial infarction with low atrial rhythm due to propyphenazone: Kounis syndrome . International Journal of Cardiology . 148 . 3 . 352–3 . May 2011 . 20541820 . 10.1016/j.ijcard.2010.05.038 .
8. Web site: Multi-Country Survey On Banned And Restricted Pharmaceuticals . Health Action International Asia Pacific . August 2008 . 7 .