| Revision as of 12:01, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456749768 of page Phenazone for the Chem/Drugbox validation project (updated: ''). |
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{{short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 408804905 |
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| verifiedrevid = 464200031 |
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| IUPAC_name = 1,2-dihydro- 1,5-dimethyl- 2-phenyl- 3''H''-pyrazol- 3-one |
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| IUPAC_name = 1,2-Dihydro-1,5-dimethyl-2-phenyl-3''H''-pyrazol-3-one |
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| image = Phenazone.svg |
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| image = Phenazone2DCSD.svg |
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| width = 200 |
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| width = 200 |
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| drug_name = Antipyrine |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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| excretion = |
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| excretion = |
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| elimination_half-life = 12 hours |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 60-80-0 |
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| CAS_number = 60-80-0 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D01776 |
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| KEGG = D01776 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 31225 |
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| ChEBI = 31225 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 277474 |
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| ChEMBL = 277474 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=11 | H=12 | N=2 | O=1 |
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| C=11 | H=12 | N=2 | O=1 |
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⚫ |
| smiles = O=C1C=C(C)N(C)N1c2ccccc2 |
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| molecular_weight = 188.226 g/mol |
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| smiles = O=C2\C=C(/N(N2c1ccccc1)C)C |
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| InChI = 1/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 |
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| InChIKey = VEQOALNAAJBPNY-UHFFFAOYAS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 |
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| StdInChI = 1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 |
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| synonyms = analgesine, antipyrine |
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| synonyms = analgesine, antipyrine |
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}} |
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'''Phenazone''' (] and ]; also known as '''phenazon''', '''antipyrine''' (]), '''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 ] (pain reducing), ] (fever reducing) and ] drug. While it predates the term, it is often classified as a ] (NSAID). Phenazone was one of the earliest synthetic medications — when it was patented in 1883, the only synthetic medical chemicals on the market were ], a ] (as well as at least one derivative of that chemical), ], and ] (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 ] (itself later withdrawn because of safety concerns), ], ] and modern NSAIDs such as ]. However, it is still available in several countries either as an ] or prescribed drug. |
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==History== |
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] 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> |
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==Preparation== |
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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 ] and ] 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 ] or ]. It ]lizes in needles which melt at {{convert|156|C}}. ] ]s it to pyridazine tetracarboxylic acid. |
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==Adverse effects== |
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Possible adverse effects include:{{citation needed|date=December 2009}} |
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* ] to ]s |
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* ] |
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* ] |
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* ] |
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==Research== |
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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> |
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==See also== |
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*], ear drops combined with ] to relieve pain and remove ] |
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*] |
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==References== |
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{{Reflist}} |
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* {{Cite EB1911|wstitle=Antipyrine|volume=2|page=134}} |
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{{Analgesics}} |
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{{Otologicals}} |
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] |
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] |
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] |