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 ;
CompTox Dashboard (EPA)	DTXSID0040705 ;
ECHA InfoCard	100.004.608
Chemical and physical data
Formula	C16H11NO2
Molar mass	249.264 g/mol g·mol−1
3D model (JSmol)	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 ;
	(verify)

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

^ Ahluwalia, V. K. (2005). Intermediates for Organic Synthesis. I. K. International. p. 262. ISBN 81-88-237-33-7.
^ 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.
^ 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.

This drug article relating to the musculoskeletal system is a stub. You can help Wikipedia by expanding it.

This analgesic-related article is a stub. You can help Wikipedia by expanding it.

[1] Ahluwalia, V. K. (2005). Intermediates for Organic Synthesis. I. K. International. p. 262. ISBN 81-88-237-33-7.

[pmid1679861-2] 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.

[pmid7916144-3] 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.

[1]

[2]

[3]