465:
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.
278:
255:
29:
499:
Cinchophen is the main active ingredient in prednoleucotropin (PLT), a medication used in the treatment of osteoarthritis in dogs. PLT may produce analgesic and anti-pyretic effects at higher doses. Osteoarthritic dogs treated with PLT have shown significant improvement of joint mobility, stiffness,
490:
Cinchophen administration should be immediately ceased if symptoms occur. There is no cure for acute cinchophen poisoning but early diagnosis and symptomatic treatments may be effective. Calcium lactate may be used to treat hives and oral or intravenous glucose can relieve gastrointestinal symptoms.
481:
Cinchophen toxicity may present 6 to 12 hours after administration. Symptoms can include hyperventilation, hyperthermia (fever), gastrointestinal discomfort, diarrhoea, hives, vomiting, delirium, hepatitis, jaundice, anorexia, convulsions, coma and death. Fatty degeneration of the heart and kidneys,
464:
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.
447:
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
491:
If glucose is given, insulin may be needed to protect the liver from further damage. Oral alkali treatments can combat acidosis and anti-emetics may be required to manage nausea and vomiting.
59:
573:
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".
944:
891:
McKellar QA, Pearson T, Galbraith EA, Boyle J, Bell G (1991). "Pharmacokinetics and clinical efficacy of a cinchophen and prednisolone combination in the dog".
41:
358:
530:
1198:
1158:
937:
504:. The effects of PLT toxicity in dogs are similar to cinchophen toxicity in humans and include hepatotoxicity and gastric ulceration.
747:
378:
92:
930:
344:
174:
1215:
234:
546:
Cutrín Prieto C, Nieto Pol E, Batalla Eiras A, Casal
Iglesias L, Pérez Becerra E, Lorenzo Zúñiga V (June 1991). "".
435:
that was first produced by
Doebner & Gieskel in 1887, it was commercially introduced in 1908 as a treatment for
1052:
500:
lameness and weight bearing capacity. When administered correctly, PLT has shown similar clinical efficacy to
482:
necrosis of hepatic cells in addition to yellow atrophy of the liver have been recorded in autopsy findings.
700:
Reichle HS (1932-02-01). "Cinchophen
Poisoning: An Attempt to Produce Toxic Cirrhosis of the Liver in Rats".
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223:
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250:
109:
598:
1129:
908:
873:
838:
797:
753:
743:
717:
682:
647:
590:
555:
526:
386:
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)
900:
865:
856:
Murrell J (2014). "Chronic pain: what are the options when NSAID treatment is inadequate?".
828:
787:
709:
674:
665:
Palmer WL, Woodall PS (1936-09-05). "Cinchophen—Is There a Safe Method of
Administration?".
637:
629:
582:
290:
183:
1061:
163:
713:
277:
254:
118:
1209:
997:
987:
904:
833:
816:
642:
617:
501:
792:
775:
473:
Cinchophen can be administered orally in tablet form or intravenously in liquid form.
51:
1236:
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992:
678:
586:
432:
266:
602:
1115:
1018:
958:
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72:
67:
143:
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1023:
869:
1137:
1095:
1079:
1074:
1013:
982:
967:
320:
154:
912:
877:
817:"Cinchophen Administration - Jaundice as an Untoward Effect: Report of Cases"
757:
721:
686:
1169:
1033:
922:
618:"The effect of salicylate and cinchophen on enzymes and metabolic processes"
429:
45:
842:
801:
651:
20:
594:
559:
1109:
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1038:
1164:
129:
28:
633:
214:
203:
453:
449:
343:
334:
954:
436:
194:
926:
776:"Toxic Hepatitis Due to Cinchophen: A Report of Three Cases"
239:
403:
1146:
1128:
1088:
1060:
1051:
1006:
975:
966:
332:
319:
289:
284:
265:
233:
213:
193:
173:
153:
128:
108:
83:
58:
40:
35:
452:damage. There is some evidence that it stimulates
142:
439:. This drug is still used, in combination with
117:
938:
8:
19:
742:. Cincinnati, Ohio: Writer's Digest Books.
667:Journal of the American Medical Association
1057:
972:
945:
931:
923:
740:Book of poisons : a guide for writers
276:
253:
162:
27:
832:
791:
641:
182:
513:
383:
363:
249:
97:
267:
18:
222:
50:
7:
780:Canadian Medical Association Journal
769:
767:
733:
731:
714:10.1001/archinte.1932.00150090045005
525:. I. K. International. p. 262.
71:
815:Parsons L, Harding WG (July 1932).
523:Intermediates for Organic Synthesis
202:
133:
100:2-phenylquinoline-4-carboxylic acid
905:10.1111/j.1748-5827.1991.tb00913.x
14:
893:Journal of Small Animal Practice
679:10.1001/jama.1936.02770360006003
307:
301:
821:California and Western Medicine
616:Lutwak-Mann C (December 1942).
391:Key:YTRMTPPVNRALON-UHFFFAOYSA-N
366:O=C(O)c1c3ccccc3nc(c1)c2ccccc2
310:
295:
1:
774:Winfield GA (February 1932).
702:Archives of Internal Medicine
738:Stevens S, Bannon A (2007).
587:10.1016/0304-3940(94)90661-0
1053:Xanthine oxidase inhibitors
870:10.12968/coan.2014.19.4.212
1274:
285:Chemical and physical data
1193:
477:Toxicity and side-effects
399:
374:
354:
88:
26:
52:International Drug Names
622:The Biochemical Journal
521:Ahluwalia VK (2005).
575:Neuroscience Letters
495:Veterinary medicine
23:
1220:Never to phase III
1130:Mitotic inhibitors
628:(10–12): 706–728.
532:978-81-88-237-33-3
1230:
1229:
1124:
1123:
1047:
1046:
634:10.1042/bj0360706
411:
410:
345:Interactive image
235:CompTox Dashboard
16:Chemical compound
1265:
1062:purine analogues
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548:Medicina Clinica
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1210:Clinical trials
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773:
772:
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729:
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673:(10): 760–764.
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17:
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1243:Aromatic acids
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1021:
1016:
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1001:
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998:Isobromindione
995:
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988:Sulfinpyrazone
985:
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970:
964:
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952:
950:
949:
942:
935:
927:
919:
918:
883:
864:(4): 212–217.
848:
807:
786:(2): 170–174.
763:
748:
727:
708:(2): 215–220.
692:
657:
608:
581:(1–2): 55–58.
565:
554:(3): 104–106.
550:(in Spanish).
538:
531:
512:
511:
509:
506:
502:phenylbutazone
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1175:Urate oxidase
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994:
993:Benzbromarone
991:
989:
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978:
974:
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969:
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956:
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749:9781599634401
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445:veterinarians
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416:(trade names
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268:ECHA InfoCard
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251:DTXSID0040705
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43:
39:
36:Clinical data
34:
30:
25:
1253:Hepatotoxins
1161:
1153:
1116:Topiroxostat
1110:Myo-inositol
1019:Atorvastatin
899:(2): 53–58.
896:
892:
886:
861:
857:
851:
827:(1): 30–33.
824:
820:
810:
783:
779:
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516:
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472:
463:
441:Prednisolone
425:
421:
417:
413:
412:
401:
224:ChEMBL348000
1206:from market
1184:Pegloticase
1179:Rasburicase
1105:Phytic acid
1070:Allopurinol
1029:Guaifenesin
1024:Fenofibrate
968:Uricosurics
328: g·mol
274:100.004.608
84:Identifiers
1258:Quinolines
1248:Analgesics
1237:Categories
1154:Cinchophen
1138:Colchicine
1096:Febuxostat
1080:Tisopurine
1075:Oxypurinol
1014:Amlodipine
983:Probenecid
508:References
414:Cinchophen
333:3D model (
321:Molar mass
184:39Y533Z02M
155:ChemSpider
110:CAS Number
93:IUPAC name
21:Cinchophen
1216:Phase III
1204:Withdrawn
1170:Sevelamer
1101:Inositols
1034:Lesinurad
1007:secondary
913:0022-4510
878:2053-0889
758:756774729
722:0730-188X
687:0002-9955
486:Treatment
430:analgesic
426:Phenaquin
422:Quinophan
46:Drugs.com
1039:Losartan
843:18742180
802:20318604
652:16747500
603:22824054
428:) is an
404:(verify)
119:132-60-5
60:ATC code
1165:aspirin
976:primary
834:1658375
643:1266862
595:7916144
560:1679861
460:History
418:Atophan
326:249.269
291:Formula
130:PubChem
76:)
70: (
68:M04AC02
1199:WHO-EM
1162:except
1159:NSAIDs
911:
876:
841:
831:
800:
793:402197
790:
756:
746:
720:
685:
650:
640:
601:
593:
558:
529:
424:, and
359:SMILES
215:ChEMBL
204:D07280
1147:Other
1089:other
599:S2CID
454:C-Fos
450:liver
443:, by
379:InChI
335:JSmol
955:gout
909:ISSN
874:ISSN
839:PMID
798:PMID
754:OCLC
744:ISBN
718:ISSN
683:ISSN
648:PMID
591:PMID
556:PMID
527:ISBN
437:gout
433:drug
195:KEGG
175:UNII
164:8274
144:8593
42:AHFS
959:M04
901:doi
866:doi
829:PMC
788:PMC
710:doi
675:doi
671:107
638:PMC
630:doi
583:doi
579:172
240:EPA
134:CID
73:WHO
1239::
1212::
907:.
897:32
895:.
872:.
862:19
860:.
837:.
825:37
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819:.
796:.
784:26
782:.
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308:N
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296:C
242:)
238:(
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