83-73-8 Usage
Description
5,7-Diiodo-8-quinolinol, also known as Iodoquinol, is a synthetic antiprotozoal drug with amebicidal properties. It is effective against both cysts and trophozoites of the E. histolytica parasite, which is responsible for causing amebiasis. The exact mechanism of action is not well understood, but it is considered the drug of choice for treating asymptomatic or moderate forms of the disease.
Uses
Used in Antiamoebic Applications:
5,7-Diiodo-8-quinolinol is used as an amebicide for the treatment of amoebiasis, a disease caused by the protozoan parasite E. histolytica. It is particularly effective against moderate intestinal amebiasis and is considered the drug of choice for this condition.
Used in Balantidiasis Treatment:
In addition to amoebiasis, 5,7-Diiodo-8-quinolinol is also used in the treatment of balantidiasis, an infection caused by the protozoan Balantidium coli. It acts as an amoebicidal agent, helping to eliminate the parasite and alleviate symptoms.
Used in Pharmaceutical Industry:
5,7-Diiodo-8-quinolinol is used in the pharmaceutical industry under various brand names, such as Quinadome (Bayer) and Yodoxin (Glenwood). These formulations make the drug more accessible and convenient for patients and healthcare providers in the treatment of the aforementioned conditions.
Originator
Diiodohydroxyquinoline,Adco Co.
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.
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).
Therapeutic Function
Antibacterial
Flammability and Explosibility
Nonflammable
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).
Purification Methods
It crystallises from xylene and is dried at 70o in a vacuum. [Beilstein 21 II 58.]
Check Digit Verification of cas no
The CAS Registry Mumber 83-73-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 3 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 83-73:
(4*8)+(3*3)+(2*7)+(1*3)=58
58 % 10 = 8
So 83-73-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H5I2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
83-73-8Relevant articles and documents
-
Papesch,Burtner
, p. 1314 (1936)
-
Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes
Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma
, p. 1121 - 1126 (2018/08/17)
Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.
Iodination of industrially important aromatic compounds with aqueous potassium triiodide
Sharma,Srivastava,Agarwal,Diwedi
, p. 433 - 436 (2016/06/13)
A new reagent system consisting of aqueous KI3in AcOH and NaIO4as oxidant has been found to be effective in iodinating a variety of commercially important aromatic substrates under ambient conditions. The presence of Na2SO3enhances the yield and the product purity. The procedure ensures high yields (72–98%) at room temperature in a short reaction time. A remarkable feature of this system is that even acidsensitive functionalities like anilines can be iodinated quantitatively.
