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Compound

Phenazone

Also called Antipyrin, Fenazone, Anodynin

Original Wikipedia articleen.wikipedia.org/wiki/Phenazone revision used (24 October 2026)

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Overview

Phenazone (INN and BAN; also known as phenazon, antipyrine (USAN), antipyrin, 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. 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antipyretics, phenazone was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen.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.[1][2] WP

Risks and side effects

Adverse effects

Possible adverse effects include: WP⚠ Wikipedia itself has flagged this text: citation needed.

  • Allergy to pyrazolones WP
  • Nausea WP
  • Agranulocytosis WP
  • Hepatotoxicity WP

Research

Research

Phenazone is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver.[3] WP

History

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. Phenazone has an elimination half life of about 12 hours.[4–7] WP

Chemistry

Formula
C11H12N2O PC
CAS number
60-80-0 PC
Molar mass (g/mol)
188.23 PC
IUPAC name (computed by PubChem)
1,5-dimethyl-2-phenylpyrazol-3-one PC
SMILES
CC1=CC(=O)N(N1C)C2=CC=CC=C2 PC
InChIKey
VEQOALNAAJBPNY-UHFFFAOYSA-N PC
PubChem CID
2206

Harm reduction information

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Sources

  1. Journal / agency Jennings, Oscar. Antipyrin and the Prevailing Epidemic. The Lancet. 11 Jan 1890. doi:10.1016/S0140-6736(02)13571-9
  2. Journal / agency Arny, H. V. The Evolution of Synthetic Medicinal Chemicals. Industrial & Engineering Chemistry. 1926-09-01. doi:10.1021/ie50201a027
  3. Other Antipyrine drugs and health products
  4. Journal / agency Schneider A, Helmstädter A. The evil of the unknown--risk-benefit evaluation of new synthetic drugs in the 19th century. Pharmazie. January 2015. PMID 25975100
  5. Journal / agency Brune K. The early history of non-opioid analgesics. Acute Pain. 1997. doi:10.1016/S1366-0071(97)80033-2
  6. Other Ravina, Enrique. The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. 2011
  7. Other Phenazone Concise Prescribing Info

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.