5031. Iodochlorhydroxyquin

Nomenclature

CAS number: 130-26-7
5-Chloro-7-iodo-8-quinolinol; 5-chloro-8-hydroxy-7-iodoquinoline; chloroiodoquin; iodochlorohydroxyquinoline; iodochloroxyquinoline; clioquinol; Amebil; Alchloquin; Amoenol; Bactol; Barquinol; Budoform (Dolder); Chinoform; Cliquinol; Eczecidin; Enteroquinol; Entero-Septol; Enterozol; Entrokin; Hi-Enterol; Iodoenterol; Nioform; Quinambicide; Rometin; Vioform (Novartis).
C9H5ClINO; mol wt 305.50.
C 35.38%, H 1.65%, Cl 11.60%, I 41.54%, N 4.58%, O 5.24%.

Description and references

Prepn: DE 117767 (1899 to Ciba); US 641491 (1900); A. Das, S. L. Mukherji, J. Org. Chem. 22, 1111 (1957). Toxicity study: Davis et al., Am. J. Trop. Med. 24, 29 (1944). Comprehensive description: G. Padmanabhan et al., Anal. Profiles Drug Subs. 18, 57-90 (1989).

Chemical structure

Properties

Brownish-yellow, bulky powder. Practically odorless. Dec ≈178-179°. uv max (water/conc. HCl): 266 nm (A1%1cm 990); (0.1N methanolic NaOH): 269 nm (A1%1cm 1120); (ethanol): 255 nm (A1%1cm 1570). One part dissolves in 43 parts of boiling alc, 128 parts chloroform, 17 parts of boiling ethyl acetate, 170 parts of cold acetic acid, 13 parts of boiling acetic acid. Almost insol in water, cold alc, ether. Soly at room temp (mg/ml): water <0.01, methanol 1.9, ethanol 1.3, ether 5.4, chloroform 14.9, 0.1N NaOH 17.3, 0.1N HCl 0.02, acetonitrile between 1.7-2.5, tetrahydrofuran between 20-100, ethyl acetate between 6.7-10, carbon disulfide between 10-20, dimethyl sulfoxide between 20-100, dimethyl acetamide between 20-100. Darkens upon exposure to light. LD50 orally in cats: 400 mg/kg (Davis).

Caution

Has been linked with the occurrence of subacute myelo-optic neuropathy (S.M.O.N. syndrome) in Japan, T. Tsubaki et al., Lancet 1, 696 (1971); see also ibid. 1, 534 (1977); J. Tateishi in Drug-Induced Sufferings T. Soda, Ed. (Excerpta Medica, New York, 1980) pp 464-472.

Therapeutic Category

Anti-infective (topical); antiamebic.

Therapeutic Category (Veterinary)

Has been used as an intestinal anti-infective.

Keywords

Antiamebic; Antiseptic/Disinfectant; Quinolines