Phenazone

{{short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 464200031

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

| image = Phenazone2DCSD.svg

| image_class = skin-invert-image

| width = 200

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

| elimination_half-life = 12 hours

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 60-80-0

| ATC_prefix = N02

| ATC_suffix = BB01

| ATC_supplemental = {{ATC|S02|DA03}}

| PubChem = 2206

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01435

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2121

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T3CHA1B51H

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01776

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

| ChEBI = 31225

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 277474

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

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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VEQOALNAAJBPNY-UHFFFAOYSA-N

| synonyms = analgesine, antipyrine

}}

Phenazone (INN and BAN; also known as phenazon, antipyrine (USAN), antipyrin,{{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 }} 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.{{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 }} 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.