Clioquinol

Bezeichnung:Clioquinol

CAS-Nr130-26-7

Englisch Name:Clioquinol

CBNumberCB7298550

SummenformelC9H5ClINO

Molgewicht305.5

MOL-Datei130-26-7.mol

Synonyma

Clioquinol

Clioquinol physikalisch-chemischer Eigenschaften

Schmelzpunkt	175-183 °C
Siedepunkt	350.4±37.0 °C(Predicted)
Dichte	1.8959 (estimate)
Dampfdruck	0Pa at 25℃
storage temp.	2-8°C
Löslichkeit	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)
Aggregatzustand	Solid
Farbe	Light Beige to Beige
Wasserlöslichkeit	<0.1 g/100 mL at 20 ºC
Merck	14,5031
BRN	153637
LogP	1.523 at 24℃
CAS Datenbank	130-26-7(CAS DataBase Reference)
NIST chemische Informationen	5-Chloro-7-iodo-8-quinolinol(130-26-7)
EPA chemische Informationen	Clioquinol (130-26-7)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25
S-Sätze:	36/37/39-45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	VC5075000
TSCA	Yes
HazardClass	6.1(b)
PackingGroup	III
HS Code	2933492250
Giftige Stoffe Daten	130-26-7(Hazardous Substances Data)
Toxizität	LD50 orally in cats: 400 mg/kg (Davis)

Gefahreninformationscode (GHS)

Clioquinol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
S-Sätze Betriebsanweisung:
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Chemische Eigenschaften
Almost white, light yellow, brownish-yellow or yellowish-grey powder.
Originator
Clioquinol,CIBA-GEIGY Corp.
Verwenden
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.
Verwenden
Used as a topical antifungal treatment
Verwenden
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.
Trademarks
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
Weltgesundheitsorganisation (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)
Allgemeine Beschreibung
Cream-colored to brownish-yellow powder. Practically odorless. Decomposes at 178-179°C. Used as a topical anti-infective.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Clioquinol is incompatible with strong oxidizing agents, strong acids, acid chlorides and acid anhydrides . Darkens on exposure to light.
Brandgefahr
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.
Sicherheitsprofil
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.
läuterung methode
It crystallises from AcOH or xylene and dry it at 70o in vacuo.[Beilstein 21 III/IV 1190.]

Clioquinol Upstream-Materialien And Downstream Produkte

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