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Clioquinol

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Clioquinol Basic information
Clioquinol Chemical Properties
  • Melting point:175-183 °C
  • Boiling point:350.4±37.0 °C(Predicted)
  • Density 1.8959 (estimate)
  • storage temp. 2-8°C
  • solubility Soluble in DMSO (>25 mg/ml), boiling alcohol ((1:43)), methanol, and chloroform ((1:120)).
  • form Solid
  • pkapKa 8.12(50%aqEtOH t=35.0±0.1 I=0.00 N2atmosphere)(Approximate)
  • Water Solubility <0.1 g/100 mL at 20 ºC
  • Merck 14,5031
  • BRN 153637
  • CAS DataBase Reference130-26-7(CAS DataBase Reference)
  • NIST Chemistry Reference5-Chloro-7-iodo-8-quinolinol(130-26-7)
  • EPA Substance Registry SystemClioquinol (130-26-7)
Safety Information
  • Hazard Codes T
  • Risk Statements 25
  • Safety Statements 36/37/39-45
  • RIDADR UN 2811 6.1/PG 3
  • WGK Germany 3
  • RTECS VC5075000
  • TSCA Yes
  • HazardClass 6.1(b)
  • PackingGroup III
  • HS Code 2933492250
  • Hazardous Substances Data130-26-7(Hazardous Substances Data)
  • ToxicityLD50 orally in cats: 400 mg/kg (Davis)
MSDS
Clioquinol Usage And Synthesis
  • Chemical PropertiesAlmost white, light yellow, brownish-yellow or yellowish-grey powder.
  • UsesClioquinol is used as an anti-infective agent; antiamoebic agent; intravaginal trichomonacide; used to impregnate cotton bandages for antibacterial purposes; in animals as an intestinal anti-infective agent.
  • Usesalpha adrenergic blocker, mydriatic, antidepressant
  • UsesUsed as a topical antifungal treatment
  • DefinitionChEBI: A monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by chlorine and iodine, respectively. It has antibacterial and atifungal properties, and is used in creams for the treatment of skin infections. It has al o been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease.
  • IndicationsIodochlorhydroxyquin (Clioquinol), containing 40% iodine, was originally developed as a substitute for iodoform as an antiseptic dusting powder. Although its most effective use is in the treatment of amebiasis, it also has mild antibacterial and antifungal effects and may be used alone or with steroids in the treatment of eczematous and impetiginized processes and some dermatophyte, yeast, and Trichomonas infections. However, more specific agents are available. Because of neurotoxicity, the oral form of this drug has been withdrawn in the United States. A recent study demonstrating significant percutaneous absorption when applied to intact human skin raises concern regarding its topical use as well. The medication may stain the skin, hair, and clothing yellow and may induce contact allergy.
  • brand nameDomeform-HC (Bayer); Quin-O-Creme (Marion Merrell Dow); Rheaform Boluses [Veterinary] (Fort Dodge Animal Health); Vioform (Ciba-Geigy);Amebio-formo;Anterobe;Aristoform "d";Aristoform "r";Barquinol hc;Betnorate-c;Britaderm;Britadex-vioform;Carboform;Cloro-yodo-hidroxi;Clorpine;Combias;Copover;Cortex;Corti-glottyl;Dependal;Dermo-quinol;Dermozolan;Dexalocal;Diaban;Dioderm c-c;Diodotracin;Dizenterol;Enteral;Ente-rivo;Enterokin;Enterosan;Entero-valodon;Entero-vioformo;Enterquinol;Entox;Entrasorb;Entrokinol;Fusalor-yodocloro;Fyloxxal;Gmd;Guanosept;Haelan-c;Hocacorten-vioform;Hydroform;Iodo-cortifair;Iodocortindon;Iodo-max;Isoderm;Khlorlinkotsin;Klinicin;Lecortin;Lederform-d;Lemoderm;Linola;Locorten-vioform;Metrijet;Metrityl;Mexafermento;Mexafom;Nasello;Nefurox;Obstecrim;Pedi-cort;Percural;Phen-ortis;Pricort cream;Propaderm-c;Quadriderm;Quin iii;Quina band;Quiniodochlor;Reticus;Sebryl;Sedacol;Septo-canulase;Silic c;Tequinophil;Toptic;Torofor;Unidiarea;Uteroject;Ventribex;Viform;Vioform bolus;Vioform hydrocortisan;Vioform hydrocortisone;Vioforme.
  • World Health Organization (WHO)Clioquinol, a halogenated hydroxyquinoline derivative, was introduced into medicine around 1900 as a topical antiseptic and in 1934 oral preparations for the treatment of amoebic dysentery and simple diarrhoea became available. By 1964 its use in Japan had been associated with cases of sub-acute myelo-optic neuropathy (SMON) which reached epidemic proportions resulting in its withdrawal there in 1970. Although relatively few cases of SMON were documented elsewhere, clioquinol was subsequently withdrawn from use in many countries and placed under prescription control in others. It was phased out worldwide by the major manufacturer between 1983 and 1985 on grounds of obsolescence. No adequately controlled evidence was ever generated to demonstrate that clioquinol is effective in bacterial or viral diarrhoea. However, products containing clioquinol and related halogenated hydroxyquinolines continue to be used in some tropical and subtropical countries where amoebiasis remains endemic. Other amoebocides are preferred in the WHO Model List of Essential Drugs. (Reference: (WHODI) WHO Drug Information, 77.1, 9, 1977)
  • General DescriptionCream-colored to brownish-yellow powder. Practically odorless. Decomposes at 178-179°C. Used as a topical anti-infective.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfileClioquinol is incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides . Darkens on exposure to light.
  • Fire HazardFlash point data for Clioquinol are not available; however, Clioquinol is probably combustible.
  • Clinical Use5-Chloro-7-iodo-8-quinolinol, 5-chloro8-hydroxy-7-iodoquinoline, or iodochlorhydroxyquin (Vioform) occursas a spongy, light-sensitive, yellowish white powder that isinsoluble in water. Vioform was initially used as a substitutefor iodoform in the belief that it released iodine in the tissues.It has been used as a powder for many skin conditions,such as atopic dermatitis, eczema, psoriasis, and impetigo.A 3% ointment or cream has been used vaginally as a treatmentfor Trichomonas vaginalis vaginitis. The best use forVioform is in the topical treatment of fungal infections suchas athlete’s foot and jock itch. A combination with hydrocortisone(Vioform HC) is also available.
  • Safety ProfilePoison by ingestion. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: change in central nervous system electrical function, optic nerve damage, and changes in vision. Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, I-, and NOx.
  • Purification MethodsIt crystallises from AcOH or xylene and dry it at 70o in vacuo.[Beilstein 21 III/IV 1190.]
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