Phenazone

Phenazone
Systematic (IUPAC) name
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
Pharmacokinetic data
Biological half-life 12 hours
Identifiers
CAS Number 60-80-0 YesY
ATC code N02BB01 (WHO) S02DA03 (WHO)
PubChem CID 2206
DrugBank DB01435 YesY
ChemSpider 2121 YesY
UNII T3CHA1B51H YesY
KEGG D01776 YesY
ChEBI CHEBI:31225 YesY
ChEMBL CHEMBL277474 YesY
Synonyms analgesine, antipyrine
Chemical data
Formula C11H12N2O
Molar mass 188.2258g/mol
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Phenazone (INN and BAN; also known as phenazon, antipyrine (USAN), or analgesine) is an analgesic, a non-steroidal anti-inflammatory drug and an antipyretic. It was first synthesized by Ludwig Knorr in 1887.[1][2]:26-27 Phenazone is synthesized[3] by condensation of phenylhydrazine and ethyl acetoacetate under basic conditions and methylation of the resulting intermediate compound 1-phenyl-3-methylpyrazolone[4] with dimethyl sulfate or methyl iodide. It crystallizes in needles which melt at 156 °C. Potassium permanganate oxidizes it to pyridazine tetracarboxylic acid. Phenazone has an elimination half life of about 12 hours.[5] Indication: Used to relieve pain and fever. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver.[6]

Adverse effects

Possible adverse effects include:

See also

References

  1. ↑ Brune, K (1997). "The early history of non-opioid analgesics". Acute Pain 1: 33. doi:10.1016/S1366-0071(97)80033-2.
  2. ↑ Enrique Ravina. The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons, 2011 ISBN 9783527326693
  3. ↑ https://books.google.ca/books?id=07g30rxCA0EC&lpg=PA225&ots=KjJPobMfjq&dq=synthesis%20of%20phenazone&pg=PA226#v=onepage&q=synthesis%20of%20phenazone&f=false
  4. ↑ http://www.chemspider.com/Chemical-Structure.63516.html
  5. ↑ http://www.mims.com/USA/drug/info/phenazone/?q=Other%20Ear%20Preparations&type=full
  6. ↑ http://www.medicatione.com/?c=ing&s=antipyrine
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