Propyphenazone

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]

Propyphenazone
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Identifiers
IUPAC name
  • 1,5-Dimethyl-2-phenyl-4-propan-2-yl-pyrazol-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.855
Chemical and physical data
FormulaC14H18N2O
Molar mass230.311 g·mol−1
3D model (JSmol)
SMILES
  • O=C1C(C(C)C)=C(C)N(C)N1c2ccccc2
InChI
  • InChI=1S/C14H18N2O/c1-10(2)13-11(3)15(4)16(14(13)17)12-8-6-5-7-9-12/h5-10H,1-4H3 Y
  • Key:PXWLVJLKJGVOKE-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)
Saridon (Combination drug with Propyphenazone) from Hoffman-La Roche, ca. 1950/60

Serious adverse events

Case reports have described acute inferior-wall myocardial infarctions characterized by low atrial rhythms (Kounis syndrome) secondary to propyphenazone use.[5]

Excerpt from WHO comments

Propyphenazone, a pyrazolone derivative with anti-inflammatory, analgesic and antipyretic activity, was introduced in 1951 for the treatment of rheumatic disorders. As it is structurally related to aminophenazone it has been associated with severe blood dyscrasias. However, it cannot be transformed into potentially carcinogenic nitrosamines and has therefore been widely used as a replacement drug for aminophenazone. In certain countries, products containing propyphenazone have now been restricted in their indications, whereas in others they are still available, sometimes as over-the-counter preparations.[6]

Banned

See also

References
  1. "Isopropylantipyrine". Drugs.com. Retrieved 8 March 2018.
  2. Göres E, Kossowicz J, Schneider HG (March 2004). "[Propyphenazone. Pharmacology and use]" [Propyphenazone. Pharmacology and use]. Medizinische Monatsschrift für Pharmazeuten (in German). 27 (3): 72–6. PMID 15032249.
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 530. ISBN 9783527607495.
  4. "SC exempts painkiller Saridon from the banned list in India". February 21, 2019 – via The Economic Times.
  5. Akyel A, Alsancak Y, Yayla Ç, Sahinarslan A, Özdemir M (May 2011). "Acute inferior myocardial infarction with low atrial rhythm due to propyphenazone: Kounis syndrome". International Journal of Cardiology. 148 (3): 352–3. doi:10.1016/j.ijcard.2010.05.038. PMID 20541820.
  6. Consolidated List of Products whose Consumption and/or Sale have been Banned, Withdrawn, Severely Restricted or not Approved by Governments, Twelfth Issue (PDF). New York: Department of Economic and Social Affairs of the United Nations Secretariat. 2005. p. 232.
  7. "Multi-Country Survey On Banned And Restricted Pharmaceuticals". Health Action International Asia Pacific. August 2008. p. 7.


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