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	249.269 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 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.^[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]

^ Ahluwalia VK (2005). Intermediates for Organic Synthesis. I. K. International. p. 262. ISBN 978-81-88-237-33-3.
^ Cutrín Prieto C, Nieto Pol E, Batalla Eiras A, Casal Iglesias L, Pérez Becerra E, Lorenzo Zúñiga V (June 1991). "[Toxic hepatitis from cinchophen: report of 3 cases]". Medicina Clinica (in Spanish). 97 (3): 104–106. 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". Neuroscience Letters. 172 (1–2): 55–58. doi:10.1016/0304-3940(94)90661-0. PMID 7916144. S2CID 22824054.

[1] Ahluwalia VK (2005). Intermediates for Organic Synthesis. I. K. International. p. 262. ISBN 978-81-88-237-33-3.

[pmid1679861-2] Cutrín Prieto C, Nieto Pol E, Batalla Eiras A, Casal Iglesias L, Pérez Becerra E, Lorenzo Zúñiga V (June 1991). "[Toxic hepatitis from cinchophen: report of 3 cases]". Medicina Clinica (in Spanish). 97 (3): 104–106. 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". Neuroscience Letters. 172 (1–2): 55–58. doi:10.1016/0304-3940(94)90661-0. PMID 7916144. S2CID 22824054.

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