Clioquinol CAS 130-26-7
Introduction：Basic information about Clioquinol CAS 130-26-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Clioquinol Basic information
| Product Name: | Clioquinol |
| Synonyms: | 5-Chlor-7-jod-8-hydroxy-chinolin;5-chloro-7-iodo-8-quinolino;7-Iodo-5-chloroxine;8-Quinolinol, 5-chloro-7-iodo-;ala-quin;Alchloquin;alchoquin;alioform |
| CAS: | 130-26-7 |
| MF: | C9H5ClINO |
| MW: | 305.5 |
| EINECS: | 204-984-4 |
| Product Categories: | Miscellaneous Compounds;Pharmaceutical intermediate;Building Blocks;C8 to C10;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Quinolines, Quinazolines and derivatives;Haloquinolines;Hydroxyquinolines;Quinolines |
| Mol File: | 130-26-7.mol |
Clioquinol Chemical Properties
| Melting point | 175-183 °C |
| Boiling point | 350.4±37.0 °C(Predicted) |
| density | 1.8959 (estimate) |
| vapor pressure | 0Pa at 25℃ |
| storage temp. | 2-8°C |
| solubility | Soluble in DMSO (>25 mg/ml), boiling alcohol ((1:43)), methanol, and chloroform ((1:120)). |
| pka | pKa 8.12(50%aqEtOH t=35.0±0.1 I=0.00 N2atmosphere)(Approximate) |
| form | Solid |
| color | Light Beige to Beige |
| Water Solubility | <0.1 g/100 mL at 20 ºC |
| Merck | 14,5031 |
| BRN | 153637 |
| Major Application | forensics and toxicology pharmaceutical (small molecule) |
| InChI | 1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H |
| InChIKey | QCDFBFJGMNKBDO-UHFFFAOYSA-N |
| SMILES | Oc1c(I)cc(Cl)c2cccnc12 |
| LogP | 1.523 at 24℃ |
| CAS DataBase Reference | 130-26-7(CAS DataBase Reference) |
| NIST Chemistry Reference | 5-Chloro-7-iodo-8-quinolinol(130-26-7) |
| EPA Substance Registry System | Clioquinol (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 | TSCA listed |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 2933492250 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1 |
| Hazardous Substances Data | 130-26-7(Hazardous Substances Data) |
| Toxicity | LD50 orally in cats: 400 mg/kg (Davis) |
| Chemical Properties | Almost white, light yellow, brownish-yellow or yellowish-grey powder. |
| Originator | Clioquinol,CIBA-GEIGY Corp. |
| Uses | alpha adrenergic blocker, mydriatic, antidepressant |
| Uses | Used as a topical antifungal treatment |
| Uses | Clioquinol 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. |
| Indications | Iodochlorhydroxyquin (Clioquinol), containing 40% iodine, was originally developedas a substitute for iodoform as an antiseptic dusting powder. Although itsmost effective use is in the treatment of amebiasis, it also has mild antibacterialand antifungal effects and may be used alone or with steroids in the treatmentof eczematous and impetiginized processes and some dermatophyte, yeast, andTrichomonas infections. However, more specific agents are available. Because ofneurotoxicity, the oral form of this drug has been withdrawn in the United States.A recent study demonstrating significant percutaneous absorption when applied tointact human skin raises concern regarding its topical use as well. The medicationmay stain the skin, hair, and clothing yellow and may induce contact allergy. |
| Definition | ChEBI: 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 alo been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease. |
| Manufacturing Process | Chlor-5-oxy-8-chinoline (18 kg) was mixed with potassium hydroxide (6.0 kg),water (400 kg) and heated. To this solution 50 L saturated aqueous solution ofpotassium iodide (16.6 kg) was added, mixed and continued to heat. Solutionwas filtered at room temperature. Then to this yellow solution the solution ofchloride of lime and 50 kg 5% solution of were added then all this was mixedand allowed to stand for 24 h .After eliminating of free iodine by addition of sodium thiosulfate the obtainedprecipitate was washed with water. To residue 1% solution of acidum hydrochloricum (50.0 kg) and rapidly was heated to 50°C. Then it was washedwith water and dried, so 5-chloro-7-iodo-quinolinol-8 was obtained, meltingpoint 170°-175°C. |
| Brand name | Domeform-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. |
| Therapeutic Function | Antibacterial |
| World Health Organization (WHO) | Clioquinol, a halogenated hydroxyquinoline derivative, wasintroduced into medicine around 1900 as a topical antiseptic and in 1934 oralpreparations for the treatment of amoebic dysentery and simple diarrhoea becameavailable. By 1964 its use in Japan had been associated with cases of sub-acutemyelo-optic neuropathy (SMON) which reached epidemic proportions resulting inits withdrawal there in 1970. Although relatively few cases of SMON weredocumented elsewhere, clioquinol was subsequently withdrawn from use in manycountries and placed under prescription control in others. It was phased outworldwide by the major manufacturer between 1983 and 1985 on grounds ofobsolescence. No adequately controlled evidence was ever generated todemonstrate that clioquinol is effective in bacterial or viral diarrhoea. However,products containing clioquinol and related halogenated hydroxyquinolinescontinue to be used in some tropical and subtropical countries where amoebiasisremains endemic. Other amoebocides are preferred in the WHO Model List ofEssential Drugs.(Reference: (WHODI) WHO Drug Information, 77.1, 9, 1977) |
| General Description | Cream-colored to brownish-yellow powder. Practically odorless. Decomposes at 178-179°C. Used as a topical anti-infective. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | Clioquinol is incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides . Darkens on exposure to light. |
| Fire Hazard | Flash point data for Clioquinol are not available; however, Clioquinol is probably combustible. |
| Flammability and Explosibility | Non flammable |
| Biological Activity | Cell permeable: no', 'Primary Target Metal ion chelator', 'Product does not compete with ATP.', 'Reversible: no |
| Clinical Use | 5-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 Profile | Poison 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 Methods | It crystallises from AcOH or xylene and dry it at 70o in vacuo.[Beilstein 21 III/IV 1190.] |
Clioquinol Preparation Products And Raw materials
| Raw materials | Hydroxide |
| Preparation Products | 5,7-Dichloro-8-hydroxyquinoline |
