5,7-Diiodo-8-quinolinol

Originator

Diiodohydroxyquinoline,Adco Co.

The Uses of 5,7-Diiodo-8-quinolinol

Iodoquinol is an amebocide used against E. histolytica, and it is active against both cysts and trophozoites that are localized in the lumen of the intestine. It is considered the drug of choice for treating asymptomatic or moderate forms of amebiasis. The mechanism of action is unknown. Iodoquinol is used for diseases caused by moderate intestinal amebiasis. Synonyms of this drug are diquinol, iodoxin, diiodoquin, amebaquin, and others.

The Uses of 5,7-Diiodo-8-quinolinol

It acts as an amoebicidal and so used in the treatment of amoebiasis, balantidiasis (an infection caused by protozoa).

Background

Diiodohydroxyquinoline, also known as uidoquinol and iodoquinol, is a quinoline derivative that can be used in the treatment of amoebiasis. The exact mechanism of action is unknown. Iodoquinol is not currently available in any FDA-approved products.

Indications

Used in the treatment of amoebiasis.

Indications

Iodoquinol (diiodohydroxyquin, Yodoxin, Moebiquin) is a halogenated 8-hydroxyquinoline derivative whose precise mechanism of action is not known but is thought to involve an inactivation of essential parasite enzymes. Iodoquinol kills the trophozoite forms of E. histolytica, B. coli, B. hominis, and Dientamoeba fragilis.
Iodoquinol is absorbed from the gastrointestinal tract and is excreted in the urine as glucuronide and sulfate conjugates. Most of an orally administered dose is excreted in the feces. Iodoquinol has a plasma half-life of about 12 hours.
Iodoquinol is the drug of choice in the treatment of asymptomatic amebiasis and D. fragilis infections. It is also used in combination with other drugs in the treatment of other forms of amebiasis and as an alternative to tetracycline in the treatment of balantidiasis.
Adverse reactions are related to the iodine content of the drug; the toxicity is often expressed as skin reactions, thyroid enlargement, and interference with thyroid function studies. Headache and diarrhea also occur. Chronic use of clioquinol, a closely related agent, has been linked to a myelitislike illness and to optic atrophy with permanent loss of vision.

Definition

ChEBI: Iodoquinol is a monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by iodine. It is considered the drug of choice for treating asymptomatic or moderate forms of amoebiasis. It has a role as an antiamoebic agent, an antibacterial agent, an antiseptic drug and an antiprotozoal drug. It is a monohydroxyquinoline and an organoiodine compound.

Manufacturing Process

5,7-Diiodo-8-quinolinol widely used as an intestinal antiseptic, especially as an antiamebic agent. It is also used topically in other infections and may cause CNS and eye damage. It is known by very many similar trade names worldwide.
0.01 mol 8-oxychinoline and 0.01 mol salicylic acid were dissolved in 500 ml of water and then 0.05 mol potassium iodide was added. The mixture was heated to temperature 90°-100°C. After that 0.01 mol of KIO3 by little tiles was added. The next tile was added after a disappearence of discharging iodine. Then 10 ml 2 N HCl was added. The solid product was fallen, filtered off, washed with hot water and in 0.25 N NaOH dissolved. The solution was filtered and the clear filtrate precipitated with a very little excess of HCl. The product 5,7-diiodo-8-quinolinol was filtered, washed with hot water and dried. MP: 200°-250°C (with decomposition).

brand name

Quinadome (Bayer); Yodoxin (Glenwood).

Therapeutic Function

Antibacterial

Flammability and Explosibility

Non flammable

Clinical Use

5,7-Diiodo-8-quinolinol, 5,7-diiodo-8-hydroxyquinoline,or diiodohydroxyquin (Yodoxin, Diodoquin, Diquinol) is ayellowish to tan microcrystalline, light-sensitive substancethat is insoluble in water. It is recommended for acute andchronic intestinal amebiasis but is not effective in extraintestinaldisease. Because a relatively high incidence of topicneuropathy has occurred with its use, iodoquinol should notbe used routinely for traveler’s diarrhea.

Safety Profile

Poison by ingestion and intravenous routes. Human systemic effects by ingestion: eye effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of Iand Nox

Synthesis

Iodoquinol, 5,7-diiodo-8-quinolinol (37.2.2), is made by iodination of 8-oxyquinoline (37.2.1) using a mixture of potassium iodide/potassium iodate. The initial 8-hydroxyquinolin (37.2.1) is made from 2-aminophenol and glycerol in the presence of sulfuric acid and nitrobenzene (Skraup synthesis).

Metabolism

Not Available

Purification Methods

It crystallises from xylene and is dried at 70o in a vacuum. [Beilstein 21 II 58.]