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| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral |
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| ECHA InfoCard | 100.006.855 |
| Chemical and physical data | |
| Formula | C14H18N2O |
| Molar mass | 230.311 g·mol−1 |
| 3D model (JSmol) | |
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Propyphenazone (known asisopropylantipyrine in Japan)[1] is a derivative ofphenazone[2] with similaranalgesic andantipyretic effects. Originally patented in 1931,[3] propyphenazone is marketed as acombination formulation withparacetamol andcaffeine for treatment ofprimary headache disorder.[4]
Case reports have described acute inferior-wallmyocardial infarctions characterized bylow atrial rhythms[vague] (Kounis syndrome) secondary to propyphenazone use.[5]
Propyphenazone, a pyrazolone derivative withanti-inflammatory, analgesic and antipyretic activity, was introduced in 1951 for the treatment ofrheumatic disorders. As it is structurally related to aminophenazone it has been associated with severe blooddyscrasias. However, it cannot be transformed into potentially carcinogenicnitrosamines and has therefore been widely used as a replacement drug foraminophenazone. In certain countries, products containing propyphenazone have now been restricted in their indications, whereas in others they are still available, sometimes asover-the-counter preparations.[6]
Propyphenazone is banned in some countries includingSri Lanka,[7]Malaysia,[7] andThailand.[7]
Ethyl 2-isopropylacetoacetate (1) andphenylhydrazine (2) are combined to form thepyrazolone ring in the intermediate (3), which isalkylated withmethyl iodide to yield propyphenazone.[8][9]
