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

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 

Yes

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2933492250

Hazardous Substances Data

130-26-7(Hazardous Substances Data)

Toxicity

LD50 orally in cats: 400 mg/kg (Davis)

MSDS

• Language:English Provider:Chloroiodeoquim
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Clioquinol Usage And Synthesis

Chemical Properties

Almost white, light yellow, brownish-yellow or yellowish-grey powder.

Originator

Clioquinol,CIBA-GEIGY Corp.

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.

Uses

alpha adrenergic blocker, mydriatic, antidepressant

Uses

Used as a topical antifungal treatment

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 al o been investigated as a chelator of copper and zinc ions for the possible treatment of Alzheimer's disease.

Indications

Iodochlorhydroxyquin (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.

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 of potassium iodide (16.6 kg) was added, mixed and continued to heat. Solution was filtered at room temperature. Then to this yellow solution the solution of chloride of lime and 50 kg 5% solution of were added then all this was mixed and allowed to stand for 24 h
. After eliminating of free iodine by addition of sodium thiosulfate the obtained precipitate was washed with water. To residue 1% solution of acidum
hydrochloricum (50.0 kg) and rapidly was heated to 50°C. Then it was washed with water and dried, so 5-chloro-7-iodo-quinolinol-8 was obtained, melting point 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, 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 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

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(130-26-7)Related Product Information

• Acid Red 94
• CHLOROPHOSPHONAZO III
• 8-Hydroxyquinoline
• Quinhydrone
• 5-Chloro-8-hydroxyquinoline
• component of Nystaform-hc
• Difluorochloromethane
• (5-CHLORO-7-IODO-QUINOLIN-8-YLOXY)-ACETIC ACID
• Clioquinol
• CLIOQUINOL IMP. A (EP): 5-CHLOROQUINOLIN-8-OL
• CLIOQUINOL IMP. C (EP): 5,7-DIIODOQUINOLIN-8-OL
• CLIOQUINOL IMP. B (EP): 5,7-DICHLOROQUINOLIN-8-OL
• 5-CHLORO-8-HYDROXY-7-IODOQUINOLINE= CLIOQUINOL
• clioquinol glucuronide
• Clioquinol(Iodochlorhydroxyquin)
• 3-[(5-chloro-7-iodoquinolin-8-yl)oxy]propanoic acid
• 2-[(5-chloro-7-iodoquinolin-8-yl)oxy]propanoic acid
• 5-CHLORO-7-IODO-8-(2-HYDROXYETHOXY)-QUINOLINE