Cinchophen

Title: Cinchophen
CAS Registry Number: 132-60-5
CAS Name: 2-Phenyl-4-quinolinecarboxylic acid
Additional Names: 2-phenylcinchoninic acid
Trademarks: Atophan (Warner-Chilcott); Quinophan; Phenoquin; Agotan; Artam; Alutyl; Cinconal; Vantyl; Viophan; Atocin; Mylofanol; Rhematan; Rheumin; Tophol; Polyphlogin; Quinofen; Tophosan
Molecular Formula: C16H11NO2
Molecular Weight: 249.26
Percent Composition: C 77.10%, H 4.45%, N 5.62%, O 12.84%
Literature References: Quinoline derivative formerly used in treatment of chronic gout: A. B. Gutman, Arthritis Rheum. 16, 431 (1973). Prepd by heating pyruvic acid with aniline and benzaldehyde or with benzylidene aniline in abs alcohol: Doebner, Gieseke, Ann. 242, 290 (1887). Also from acetophenone and isatinic acid in alcoholic KOH: Pfitzinger, J. Prakt. Chem. 38, 582 (1882); 56, 293 (1897). Cinchophen as ulcerogenic agent: T. P. Churchill, F. H. van Wagoner, Arch. Pathol. 13, 850 (1932); N. Umeda et al., Toxicol. Appl. Pharmacol. 18, 102 (1971); T. H. Stewart et al., J. Pathol. 131, 363 (1980). Mitochondrial toxicity of cinchophen and derivatives: H. Vainio et al., Biochem. Pharmacol. 20, 1589 (1971).
Properties: Needles, mp 213-216°. Stable to air, but turns yellow under the influence of light. Slightly bitter taste. Practically insol in water. One gram dissolves in about 400 ml chloroform, in about 100 ml ether and in about 120 ml alcohol.
Melting point: mp 213-216°
Derivative Type: Hydrochloride
CAS Registry Number: 132-58-1
Trademarks: Chloroxyl
Molecular Formula: C16H11NO2.HCl
Molecular Weight: 285.72
Percent Composition: C 67.26%, H 4.23%, N 4.90%, O 11.20%, Cl 12.41%
Properties: Yellow cryst powder, slightly bitter, astringent taste; mp about 223°. Practically insol in water. Slightly sol in alcohol; sol in chloroform, ether.
Melting point: mp about 223°
Derivative Type: Allyl ester
CAS Registry Number: 524-34-5
Additional Names: Allyl 2-phenylcinchoninate
Trademarks: Atoquinol
Molecular Formula: C19H15NO2
Molecular Weight: 289.33
Percent Composition: C 78.87%, H 5.23%, N 4.84%, O 11.06%
Literature References: Prepn: Gams, US 1336952 (1920).
Properties: Long needles from alc, mp 30°. bp15 260°. Practically insol in water. Readily sol in alcohol, ether, acetone, oils. Tasteless.
Melting point: mp 30°
Boiling point: bp15 260°
Use: Experimentally to induce ulcers.
Therap-Cat: Formerly as analgesic.
Keywords: Analgesic (Non-Narcotic).
Cinchotoxine Cinepazet Cinepazide Cinerins Cinidon-ethyl

Cinchophen
Cinchophen.svg
Systematic (IUPAC) name
2-phenylquinoline-4-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 132-60-5
ATC code M04AC02
PubChem CID 8593
ChemSpider 8274 YesY
UNII 39Y533Z02M YesY
KEGG D07280 YesY
ChEMBL CHEMBL348000 YesY
Chemical data
Formula C16H11NO2 
Mol. mass 249.264 g/mol
 YesY (what is this?)  (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.

Use of this drug in humans ceased in the 1930s due to the discovery that cinchophen can cause serious liver damage.[1]

There is some evidence that it stimulates C-Fos.[2]