Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Phenazone: Difference between pages

{{short description|Chemical compound}}

| Watchedfields = changed

| verifiedrevid = 464200031

| IUPAC_name = 1,2-Dihydro-1,5-dimethyl-2-phenyl-3''H''-pyrazol-3-one

| image = Phenazone2DCSD.svg

| elimination_half-life = 12 hours

| ChEBI_Ref = {{ebicite|correct|EBI}}

| C=11 | H=12 | N=2 | O=1

| smiles = O=C1C=C(C)N(C)N1c2ccccc2

'''Phenazone''' ([[International Nonproprietary Name|INN]] and [[British Approved Name|BAN]]; also known as '''phenazon''', '''antipyrine''' ([[United States Adopted Name|USAN]]), '''antipyrin''',<ref>{{cite journal |last1=Jennings |first1=Oscar |title=Antipyrin and the Prevailing Epidemic |journal=The Lancet |date=11 Jan 1890 |volume=135 |issue=3463 |pages=105–106 |doi=10.1016/S0140-6736(02)13571-9 |url=https://zenodo.org/record/1986696 }}</ref> or '''analgesine''') is an [[analgesic]] (pain reducing), [[antipyretic]] (fever reducing) and [[anti-inflammatory]] drug. While it predates the term, it is often classified as a [[nonsteroidal anti-inflammatory drug]] (NSAID). Phenazone was one of the earliest synthetic medications — when it was patented in 1883, the only synthetic medical chemicals on the market were [[chloral hydrate]], a [[sedative]] (as well as at least one derivative of that chemical), [[trimethylamine]], and [[iodol]] (tetraiodopyrrol), an early antiseptic.<ref name="EvoSynthMed">{{cite journal |title=The Evolution of Synthetic Medicinal Chemicals |journal=Industrial & Engineering Chemistry |date=1926-09-01 |last=Arny |first=H. V. |volume=18 |issue=9 |pages=949–952 |doi=10.1021/ie50201a027 |url=https://pubs.acs.org/doi/abs/10.1021/ie50201a027 |accessdate=2022-08-11 }}</ref> One of the earliest widely used analgesics and antipyretics, phenazone was gradually replaced in common use by other medications including [[phenacetin]] (itself later withdrawn because of safety concerns), [[aspirin]], [[paracetamol]] and modern NSAIDs such as [[ibuprofen]]. However, it is still available in several countries either as an [[over-the-counter]] or prescribed drug.

==History==

[[Ludwig Knorr]] was the first to synthesize phenazone, then called antipyrine, in the early 1880s. Sources disagree on the exact year of discovery, but Knorr patented the chemical in 1883.<ref>{{cite journal |vauthors=Schneider A, Helmstädter A |title=The evil of the unknown--risk-benefit evaluation of new synthetic drugs in the 19th century |journal=Pharmazie |volume=70 |issue=1 |pages=60–3 |date=January 2015 |pmid=25975100 |doi= |url=}}</ref><ref>{{Cite journal | doi = 10.1016/S1366-0071(97)80033-2 | title = The early history of non-opioid analgesics | year = 1997 | vauthors = Brune K | journal = Acute Pain | volume = 1 | pages = 33–40 }}</ref><ref name=Ravina>{{cite book | first = Enrique | last = Ravina | name-list-style = vanc | title = The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs | publisher = John Wiley & Sons | date = 2011 | isbn = 9783527326693 }}</ref>{{rp|26–27}} Phenazone has an elimination half life of about 12 hours.<ref>{{cite web | title = Phenazone Concise Prescribing Info | url = https://www.mims.com/philippines/drug/info/phenazone?mtype=generic | work = MIMS|url-access=registration }}</ref>

==Preparation==

Phenazone is synthesized<ref name="med chem">{{cite book |isbn=8122415652|title=Medicinal Chemistry| vauthors = Kar A |year=2005|publisher=New Age International }}{{rp|226}}</ref> by condensation of [[phenylhydrazine]] and [[ethyl acetoacetate]] under basic conditions and methylation of the resulting intermediate compound 1-phenyl-3-methylpyrazolone<ref name="Chem">{{cite web |title=5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one|url=http://www.chemspider.com/Chemical-Structure.63516.html |website=Chemspider |access-date=February 24, 2019}}</ref> with [[dimethyl sulfate]] or [[methyl iodide]]. It [[crystal]]lizes in needles which melt at {{convert|156|C}}. [[Potassium permanganate]] [[oxidize]]s it to pyridazine tetracarboxylic acid.

==Adverse effects==

Possible adverse effects include:{{citation needed|date=December 2009}}

* [[Allergy]] to [[pyrazolone]]s

* [[Nausea]]

* [[Agranulocytosis]]

* [[Hepatotoxicity]]

==Research==

Phenazone is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver.<ref>{{cite web |url= https://www.sdrugs.com/?c=ing&s=antipyrine |title=Antipyrine drugs and health products |website=sDrugs.com }}</ref>

==See also==

*[[A/B Otic Drops]], ear drops combined with [[benzocaine]] to relieve pain and remove [[cerumen]]

*[[Propyphenazone]]

==References==

{{Reflist}}

* {{Cite EB1911|wstitle=Antipyrine|volume=2|page=134}}

{{Analgesics}}

{{Otologicals}}

[[Category:Pyrazolones]]

[[Category:Nonsteroidal anti-inflammatory drugs]]

[[Category:Antipyretics]]