Phenazone

Phenazone
Clinical data
Other names	analgesine, antipyrine
ATC code	N02BB01 (WHO) S02DA03 (WHO);
Pharmacokinetic data
Elimination half-life	12 hours
Identifiers
	IUPAC name 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one;
CAS Number	60-80-0 ;
PubChem CID	2206;
DrugBank	DB01435 ;
ChemSpider	2121 ;
UNII	T3CHA1B51H;
KEGG	D01776 ;
ChEBI	CHEBI:31225 ;
ChEMBL	ChEMBL277474 ;
CompTox Dashboard (EPA)	DTXSID6021117 ;
ECHA InfoCard	100.000.442
Chemical and physical data
Formula	C11H12N2O
Molar mass	188.2258g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2\C=C(/N(N2c1ccccc1)C)C;
	InChI InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 ; Key:VEQOALNAAJBPNY-UHFFFAOYSA-N ;
	(verify)

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:^{[citation needed]}

References

^ 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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[1] Brune, K (1997). "The early history of non-opioid analgesics". Acute Pain. 1: 33. doi:10.1016/S1366-0071(97)80033-2.

[Ravina-2] Enrique Ravina. The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons, 2011 ISBN 9783527326693

[3] ttps://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] ttp://www.chemspider.com/Chemical-Structure.63516.html

[5] ttp://www.mims.com/USA/drug/info/phenazone/?q=Other%20Ear%20Preparations&type=full

[6] ttp://www.medicatione.com/?c=ing&s=antipyrine

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v t e Drugs used for diseases of the ear (S02)
Infection	Acetic acid Aluminium acetotartrate Aluminium triacetate (Burow's solution) Boric acid Chloramphenicol Chlorhexidine Ciprofloxacin Clioquinol Gentamicin Hydrogen peroxide Miconazole Neomycin Nitrofurazone Ofloxacin Polymyxin B Rifamycin Tetracycline
Corticosteroids	Betamethasone Dexamethasone Fluocinolone acetonide Hydrocortisone Prednisolone
Analgesics and anesthetics	Lidocaine Cocaine Phenazone

Adverse effects

See also

References