Phenazone

In today's world, Phenazone has become a topic of increasing importance and interest for various areas of society. Both on a personal and professional level, Phenazone plays a fundamental role in the development and evolution of people and communities. Throughout history, Phenazone has been the subject of study, debate and analysis, and its influence extends to multiple disciplines, from science and technology to art and culture. In this article, we will explore in depth the impact of Phenazone on today's society, addressing its implications, applications and challenges from different perspectives. Additionally, we will examine how Phenazone has shaped the way we think, act, and relate to the world around us, and how its continued evolution continues to impact our lives in significant ways.

Phenazone
Clinical data
Other namesanalgesine, antipyrine
ATC code
Pharmacokinetic data
Elimination half-life12 hours
Identifiers
  • 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.442 Edit this at Wikidata
Chemical and physical data
FormulaC11H12N2O
Molar mass188.230 g·mol−1
3D model (JSmol)
  • O=C1C=C(C)N(C)N1c2ccccc2
  • InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 checkY
  • Key:VEQOALNAAJBPNY-UHFFFAOYSA-N checkY
  (verify)

Phenazone (INN and BAN; also known as phenazon, antipyrine (USAN), antipyrin,[1] 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.[2] 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antipyretics, phenazone was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen.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.[3][4][5]: 26–27  Phenazone has an elimination half life of about 12 hours.[6]

Preparation

Phenazone is synthesized[7] by condensation of phenylhydrazine and ethyl acetoacetate under basic conditions and methylation of the resulting intermediate compound 1-phenyl-3-methylpyrazolone[8] with dimethyl sulfate or methyl iodide. It crystallizes in needles which melt at 156 °C (313 °F). Potassium permanganate oxidizes it to pyridazine tetracarboxylic acid.

Adverse effects

Possible adverse effects include:[citation needed]

Research

Phenazone is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver.[9]

See also

References

  1. ^ Jennings, Oscar (11 Jan 1890). "Antipyrin and the Prevailing Epidemic". The Lancet. 135 (3463): 105–106. doi:10.1016/S0140-6736(02)13571-9.
  2. ^ Arny, H. V. (1926-09-01). "The Evolution of Synthetic Medicinal Chemicals". Industrial & Engineering Chemistry. 18 (9): 949–952. doi:10.1021/ie50201a027. Retrieved 2022-08-11.
  3. ^ Schneider A, Helmstädter A (January 2015). "The evil of the unknown--risk-benefit evaluation of new synthetic drugs in the 19th century". Pharmazie. 70 (1): 60–3. PMID 25975100.
  4. ^ Brune K (1997). "The early history of non-opioid analgesics". Acute Pain. 1: 33–40. doi:10.1016/S1366-0071(97)80033-2.
  5. ^ Ravina E (2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. ISBN 9783527326693.
  6. ^ "Phenazone Concise Prescribing Info". MIMS.
  7. ^ Kar A (2005). Medicinal Chemistry. New Age International. ISBN 8122415652.: 226 
  8. ^ "5-Methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one". Chemspider. Retrieved February 24, 2019.
  9. ^ "Antipyrine drugs and health products". sDrugs.com.