Propyphenazone (known as isopropylantipyrine in Japan) is a derivative of

phenazone Phenazone (International Nonproprietary Name, INN and British Approved Name, BAN; also known as phenazon, antipyrine (United States Adopted Name, USAN), antipyrin, or analgesine) is an analgesic (pain reducing), antipyretic (fever reducing) and an ...

with similar

analgesic An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...

and

antipyretic An antipyretic (, from ''anti-'' 'against' and ' 'feverish') is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which r ...

effects. Originally patented in 1931, propyphenazone is marketed as a combination formulation with

paracetamol Paracetamol, or acetaminophen, is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. It is a widely available over-the-counter drug sold under various brand names, including Tylenol and Panadol. Parac ...

and

caffeine Caffeine is a central nervous system (CNS) stimulant of the methylxanthine chemical classification, class and is the most commonly consumed Psychoactive drug, psychoactive substance globally. It is mainly used for its eugeroic (wakefulness pr ...

for treatment of

primary headache disorder The International Classification of Headache Disorders (ICHD) is a detailed hierarchical classification of all headache-related disorders published by the International Headache Society. It is considered the official classification of headaches ...

Serious adverse events

Case reports have described acute inferior-wall

myocardial infarction A myocardial infarction (MI), commonly known as a heart attack, occurs when Ischemia, blood flow decreases or stops in one of the coronary arteries of the heart, causing infarction (tissue death) to the heart muscle. The most common symptom ...

s characterized by low atrial rhythms (

Kounis syndrome Kounis syndrome is defined as acute coronary syndrome (symptoms such as chest pain relating to reduced blood flow to the heart) caused by an allergic reaction or a strong immune reaction to a drug or other substance. It is a rare syndrome with aut ...

) secondary to propyphenazone use.

Excerpt from WHO comments

Banned

Propyphenazone is banned in some countries including

Sri Lanka Sri Lanka, officially the Democratic Socialist Republic of Sri Lanka, also known historically as Ceylon, is an island country in South Asia. It lies in the Indian Ocean, southwest of the Bay of Bengal, separated from the Indian subcontinent, ...

Malaysia Malaysia is a country in Southeast Asia. Featuring the Tanjung Piai, southernmost point of continental Eurasia, it is a federation, federal constitutional monarchy consisting of States and federal territories of Malaysia, 13 states and thre ...

, and

Thailand Thailand, officially the Kingdom of Thailand and historically known as Siam (the official name until 1939), is a country in Southeast Asia on the Mainland Southeast Asia, Indochinese Peninsula. With a population of almost 66 million, it spa ...

Synthesis

Ethyl 2-isopropylacetoacetate (1) and

phenylhydrazine Phenylhydrazine is the chemical compound with the formula . It is often abbreviated as . It is also found in edible mushrooms. Properties Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow ...

(2) are combined to form the

pyrazolone Pyrazolone is 5-membered heterocycle containing two adjacent nitrogen atoms. It can be viewed as a derivative of pyrazole possessing an additional ketone, carbonyl (C=O) group. Compounds containing this functional group are useful commercially in ...

ring in the intermediate (3), which is

alkylated Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

with

methyl iodide Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one h ...

to yield propyphenazone.

References

{{Analgesics Analgesics Antipyretics Pyrazolones Isopropyl compounds

Serious adverse events

Excerpt from WHO comments

Banned

Synthesis

See also

References