Iodoquinol

Base Information

• Chemical Name: Iodoquinol
• CAS No.: 83-73-8
• Molecular Formula: C9H5I2NO
• Molecular Weight: 396.954
• Hs Code.: 29334900
• European Community (EC) Number: 201-497-9
• NSC Number: 757077,8704
• UNII: 63W7IE88K8
• DSSTox Substance ID: DTXSID6023155
• Nikkaji Number: J4.643D
• Wikipedia: Diiodohydroxyquinoline
• Wikidata: Q5276473
• NCI Thesaurus Code: C76008
• RXCUI: 3435
• Pharos Ligand ID: W9GZSMGQHXKP
• Metabolomics Workbench ID: 67460
• ChEMBL ID: CHEMBL86754
• Mol file: 83-73-8.mol

Synonyms:Diiodohydroxyquin;Diiodohydroxyquinoline;Diiodoquin;Diodoquin;Diodoxyquinoline;Diquinol;Entero Diyod;Entero-Diyod;EnteroDiyod;Entodiba;Iodoquinol;Sebaquin;Yodoxin

Chemical Property of Iodoquinol

Chemical Property:

• Vapor Pressure: 4.96E-07mmHg at 25°C
• Melting Point: >200 °C (dec.)(lit.)
• Refractive Index: 1.828
• Boiling Point: 401.8 °C at 760 mmHg
• PKA: pKa 8.0 (Uncertain)
• Flash Point: 196.8 °C
• PSA: 33.12000
• Density: 2.491 g/cm³
• LogP: 3.14960
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Ethyl Acetate (Slightly, Heated)
• Water Solubility.: 1g/L at 26℃
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 396.84606
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

97%-100.5% ^*data from raw suppliers

Iodoquinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C(C=C2I)I)O)N=C1
• Uses: 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. It acts as an amoebicidal and so used in the treatment of amoebiasis, balantidiasis (an infection caused by protozoa).
• 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.
• Therapeutic Function: Antibacterial
• 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.

Technology Process of Iodoquinol

There total 11 articles about Iodoquinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

8-quinolinol (148-24-3,24804-14-6) → 5,7-diiodo-8-hydroxyquinoline (83-73-8)

Guidance literature:

With hydrogenchloride; sodium chlorite; sodium iodide; In methanol; at 20 ℃; for 0.666667h;

DOI:10.1016/j.tet.2007.10.062

Reference yield:

1-(5,7-diiodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate (220819-28-3) → 5,7-diiodo-8-hydroxyquinoline (83-73-8) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + metronidazole (443-48-1) + 1,2-benzenedicarboxylic acid, mono[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]ester (126613-32-9)

Guidance literature:

With phosphate buffer; potassium chloride; In methanol; at 37 ℃; Rate constant; var. pH; also with human plasma and rat liver homogenate;

Reference yield:

1-(5,7-diiodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>butandioate (220819-23-8) → 5,7-diiodo-8-hydroxyquinoline (83-73-8) + succinic acid (110-15-6) + metronidazole (443-48-1) + 4-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy]-4-oxobutanoic acid (13182-87-1)

Guidance literature:

With phosphate buffer; potassium chloride; In methanol; at 37 ℃; Rate constant; var. pH; also with human plasma and rat liver homogenate;

upstream raw materials:

8-quinolinol

1-(5,7-diiodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>butandioate

1-(5,7-diiodoquinolin-8-yl)-4-<2-(2-methyl-5-nitro-1H-imidazolyl)ethyl>phthalate

hydrogenchloride

Downstream raw materials:

4-chloro-benzenesulfonic acid 5,7-diiodo-quinolin-8-yl ester

2-(4-fluorophenyl)-5-[(4-fluorophenyl)ethynyl]furo[3,2-h]quinoline

2-(3-chlorophenyl)-5-[(3-chlorophenyl)ethynyl]furo[3,2-h]quinoline

2-phenyl-5-(phenylethynyl)furo[3,2-h]quinoline

Refernces

• 1、 -. "One-pot method for preparing chloroquine chloroquine and diiodoquinoline". . . Retrieved 2021/08/25.
• 2、 -. "NOVEL RECYCLABLE IODINATING AGENT AND ITS APPLICATIONS". Page/Page column 18-19. . Retrieved 2016/11/07.