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Clioquinol

CAS No.130-26-7
Chemical Name:Clioquinol
CBNumber:CB7298550
Molecular Formula:C9H5ClINO
Formula Weight:305.5
MOL File:130-26-7.mol

Clioquinol Property

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)
EWG's Food Scores 1
FDA UNII 7BHQ856EJ5
NCI Drug Dictionary clioquinol
ATC code D08AH30,D09AA10,G01AC02,P01AA02,P01AA52,S02AA05
NIST Chemistry Reference 5-Chloro-7-iodo-8-quinolinol(130-26-7)
EPA Substance Registry System Clioquinol (130-26-7)
UNSPSC Code 41116107
NACRES NA.77

Safety

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)

NFPA 704:

	1
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H301-H315-H317-H319
Precautionary statements P261-P264-P280-P301+P310-P302+P352-P305+P351+P338

Clioquinol Price More Price(6)

Brand: Sigma-Aldrich(India)
Product number: 33931
Product name : Clioquinol
Purity: VETRANAL?, analytical standard
Packaging: 100MG
Price: ₹6819.75
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 24880
Product name : 5-Chloro-7-iodo-8-quinolinol
Purity: ≥95.0% (HPLC)
Packaging: 100G
Price: ₹10543.55
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 24880
Product name : 5-Chloro-7-iodo-8-quinolinol
Purity: ≥95.0% (HPLC)
Packaging: 500G
Price: ₹27571.28
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 233165
Product name : Clioquinol - CAS 130-26-7 - Calbiochem
Purity: A metal ion chelator that crosses the blood brain barrier and acts as a neurotoxic antibiotic.
Packaging: 1G
Price: ₹5880
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: C0187
Product name : 5-Chloro-8-hydroxy-7-iodoquinoline
Purity:
Packaging: 25G
Price: ₹2900
Updated: 2022/05/26
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Clioquinol Chemical Properties,Usage,Production

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 Used as a topical antifungal treatment
Uses alpha adrenergic blocker, mydriatic, antidepressant
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.
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.
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
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.]