Phenazone
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| Systematic (IUPAC) name | |
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1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
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| Pharmacokinetic data | |
| Biological half-life | 12 hours |
| Identifiers | |
| CAS Number | 60-80-0  |
| ATC code | N02BB01 S02DA03 |
| PubChem | CID 2206 |
| DrugBank | DB01435 |
| ChemSpider | 2121 |
| UNII | T3CHA1B51H |
| KEGG | D01776 |
| ChEBI | CHEBI:31225 |
| ChEMBL | CHEMBL277474 |
| 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[edit]
Possible adverse effects include:[citation needed]
See also[edit]
- Propyphenazone
- A/B Otic Drops, ear drops combined with benzocaine to relieve pain and remove cerumen
References[edit]
- ^ Brune, K (1997). "The early history of non-opioid analgesics". Acute Pain 1: 33. doi:10.1016/S1366-0071(97)80033-2.
- ^ Enrique Ravina. The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons, 2011 ISBN 9783527326693
- ^ 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
- ^ http://www.chemspider.com/Chemical-Structure.63516.html
- ^ http://www.mims.com/USA/drug/info/phenazone/?q=Other%20Ear%20Preparations&type=full
- ^ http://www.medicatione.com/?c=ing&s=antipyrine
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