Propyphenazone

Propyphenazone

Systematic (IUPAC) name
1,5-Dimethyl-2-phenyl-4-propan-2-yl-pyrazol-3-one
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
Identifiers
CAS Number	479-92-5
ATC code	N02BB04 (WHO)
PubChem	CID 3778
ChemSpider	3646
UNII	OED8FV75PY
ChEBI	CHEBI:135538
ChEMBL	CHEMBL28318
Chemical data
Formula	C14H18N2O
Molar mass	230.306 g/mol
SMILES O=C2\C(=C(/N(N2c1ccccc1)C)C)C(C)C
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 Key:PXWLVJLKJGVOKE-UHFFFAOYSA-N
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Propyphenazone is a derivative of phenazone^[1] with similar analgesic and antipyretic effects.

Adverse effects of propyphenazone

There have been case reports describing risk of acute inferior myocardial infarction with low atrial rhythm due to propyphenazone (Kounis syndrome).^[2]

Countries that have banned propyphenazone

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.”^[3]

• Sri Lanka^[4]
• South Korea^[4] - as reported by PharmAsia News in 2009:

“Amid rising claims that it isn't moving fast enough to counter public concern over the safety of OTC painkillers, Korea FDA has banned Bayer Korea's painkiller Saridon-A, Samjin Pharm's Geworin and 26 other products from being prescribed or sold over the counter to those under 15 years of age.”^[5]

• Malaysia^[4]
• Thailand^[4]
• Turkey - production and sale banned in January 1986 due to incidence of severe adverse reactions.^[3]
• India- Still in use. Saridon tablets contain 150 mg/tablet.

References

1. Göres, E.; Kossowicz, J.; Schneider, H. G. (2004). "Propyphenazone. Pharmacology and use" [Propyphenazone. Pharmacology and use]. Medizinische Monatsschrift für Pharmazeuten (in German) 27 (3): 72–76. PMID 15032249.
2. Akyel, A.; Alsancak, Y.; Yayla, Ç. R.; Şahinarslan, A.; Özdemir, M. (2011). "Acute inferior myocardial infarction with low atrial rhythm due to propyphenazone: Kounis syndrome". International Journal of Cardiology 148 (3): 352–353. doi:10.1016/j.ijcard.2010.05.038. PMID 20541820.
3. 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.
4. "Multi-Country Survey On Banned And Restricted Pharmaceuticals". Health Action International Asia Pacific. August 2008. p. 7.
5. "Bayer’s Saridon-A Among 28 Painkillers Banned To Those Under 15 In Korea". PharmAsia News. 2009-03-12.