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cinchophen

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Cinchophen (trade names Atophan, Quinophan, and Phenaquin) is an analgesic drug that was first produced by Doebner & Gieskel in 1887, it was commercially introduced in 1908 as a treatment for gout. This drug is still used, in combination with Prednisolone, by veterinarians to treat arthritis in animals. It can be prepared starting from anilin, benzaldehyde and pyruvic acid in absolute ethanol. Use of this drug in humans ceased in the 1930s due to the discovery that cinchophen can cause serious liver damage. There is some evidence that it stimulates C-Fos.

Wikidata facts

Mass
249.079
Show 3 more facts
chemical formula
C₁₆H₁₁NO₂
canonical SMILES
C1=CC=C(C=C1)C2=NC3=CC=CC=C3C(=C2)C(=O)O
melting point
215.0
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6 sections
Contents
  • History
  • Available forms
  • Toxicity and side-effects
  • Treatment
  • Veterinary medicine
  • References

Cinchophen (trade names Atophan, Quinophan, and Phenaquin) is an analgesic drug that was first produced by Doebner & Gieskel in 1887, it was commercially introduced in 1908 as a treatment for gout. This drug is still used, in combination with Prednisolone, by veterinarians to treat arthritis in animals. It can be prepared starting from anilin, benzaldehyde and pyruvic acid in absolute ethanol. Use of this drug in humans ceased in the 1930s due to the discovery that cinchophen can cause serious liver damage. There is some evidence that it stimulates C-Fos.

== History == Cinchophen was first introduced in 1908 as 'Atophan' and used for the treatment of gout and arthritis. It was efficacious at reducing the buildup of uric acid and became a popular medicine. Further studies in 1911 and 1912 were successful in isolating metabolites of cinchophen from human urine. During the 1920s, cases of severe adverse effects such as liver damage and cirrhosis had been clinically observed; the first case of jaundice was recorded in 1923 and the first fatality occurred in 1925. Approximately half of all patients experienced toxic effects and by 1932 there were 32 drugs available that contained cinchophen or its derivatives as their active ingredients, experiments were conducted to determine the drugs pharmacology but the mechanism of drug induced liver injury remained unclear. Cinchophen was considered to be too dangerous for human use in most countries but has applications in veterinary medicine as a treatment for osteoarthritis in dogs.

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