Cinchophen

Cinchophen

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	M04AC02 (WHO)
Identifiers
IUPAC name 2-phenylquinoline-4-carboxylic acid
CAS Number	132-60-5
PubChem (CID)	8593
ChemSpider	8274
UNII	39Y533Z02M
KEGG	D07280
ChEMBL	CHEMBL348000
ECHA InfoCard	100.004.608
Chemical and physical data
Formula	C16H11NO2
Molar mass	249.264 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)c1c3ccccc3nc(c1)c2ccccc2
InChI InChI=1S/C16H11NO2/c18-16(19)13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H,(H,18,19) Key:YTRMTPPVNRALON-UHFFFAOYSA-N
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Cinchophen (trade names Atophan, Quinophan, and Phenaquin) is an analgesic drug that was introduced in 1910 and frequently used to treat 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.^[1]

Use of this drug in humans ceased in the 1930s due to the discovery that cinchophen can cause serious liver damage.^[2]

There is some evidence that it stimulates C-Fos.^[3]

References

1. Ahluwalia, V. K. (2005). Intermediates for Organic Synthesis. I. K. International. p. 262. ISBN 81-88-237-33-7.
2. Cutrín Prieto C, Nieto Pol E, Batalla Eiras A, Casal Iglesias L, Pérez Becerra E, Lorenzo Zúñiga V (1991). "[Toxic hepatitis from cinchophen: report of 3 cases]". Medicina clínica (in Spanish). 97 (3): 104–6. PMID 1679861.
3. Takayama K, Xiong Y, Miura M (May 1994). "Neuronal expression of Fos protein in the paraventricular nucleus of the hypothalamus after i.p. injection of ulcergenic cinchophen". Neurosci. Lett. 172 (1–2): 55–8. doi:10.1016/0304-3940(94)90661-0. PMID 7916144.