Clioquinol

Base Information

• Chemical Name: Clioquinol
• CAS No.: 130-26-7
• Deprecated CAS: 22112-03-4,736176-41-3,736176-41-3
• Molecular Formula: C9H5ClINO
• Molecular Weight: 305.502
• Hs Code.: 2933492250
• European Community (EC) Number: 204-984-4
• NSC Number: 759822,3531
• UNII: 7BHQ856EJ5
• DSSTox Substance ID: DTXSID7022837
• Nikkaji Number: J5.432A
• Wikipedia: Clioquinol
• Wikidata: Q5134338
• NCI Thesaurus Code: C65337
• Pharos Ligand ID: WLRD5GQVXPB1
• Metabolomics Workbench ID: 149246
• ChEMBL ID: CHEMBL497
• Mol file: 130-26-7.mol

Synonyms:5 Chloro 7 iodo 8 quinolinol;5-Chloro-7-iodo-8-quinolinol;Chinoform;Chloroiodoquine;Clioquinol;Entero Septol;Entero Vioform;Entero-Septol;Entero-Vioform;Enteroquinol;EnteroSeptol;EnteroVioform;Iodochlorhydroxyquin;Iodochloroxyquinoline;Vioform

Chemical Property of Clioquinol

Chemical Property:

• Appearance/Colour: Cream-colored to brownish-yellow powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 175-183 °C
• Refractive Index: 1.753
• Boiling Point: 350.424 °C at 760 mmHg
• PKA: pKa 8.12(50%aqEtOH t=35.0±0.1 I=0.00 N2atmosphere)(Approximate)
• Flash Point: 165.731 °C
• PSA: 33.12000
• Density: 2.047 g/cm³
• LogP: 3.19840
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (>25 mg/ml), boiling alcohol ((1:43)), methan
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 304.91044
• Heavy Atom Count: 13
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

Clioquinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: C1=CC2=C(C(=C(C=C2Cl)I)O)N=C1
• Recent ClinicalTrials: Add-on Clioquinol in Drug-resistant Childhood Epilepsy: an Exploratory Study
• Recent EU Clinical Trials: Add-on clioquinol in drug-resistant childhood epilepsy: an exploratory study
• 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. alpha adrenergic blocker, mydriatic, antidepressant Used as a topical antifungal treatment
• 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.
• Therapeutic Function: Antibacterial
• 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.

Technology Process of Clioquinol

There total 13 articles about Clioquinol 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: 94.0%

5-Chloro-8-hydroxyquinoline (130-16-5) → 5-chloro-7-iodoquinolin-8-ol (130-26-7,22112-03-4)

Guidance literature:

With 1-butyl-3-methyl-pyridinium dichloroiodate; at 80 ℃; for 1h; Inert atmosphere;

Reference yield: 65.0%

8-hydroxy-7-iodoquinoline (7385-89-9) → 5-chloro-7-iodoquinolin-8-ol (130-26-7,22112-03-4)

Guidance literature:

With trichloroisocyanuric acid; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1039/c7sc04107a

Reference yield:

5-chloro-7-iodo-8-quinolinyl-β-D-glucopyranoside (1371439-48-3) → β-D-glucose (492-61-5) + 5-chloro-7-iodoquinolin-8-ol (130-26-7,22112-03-4)

Guidance literature:

With β-glucosidase from almonds; water; at 37 ℃; for 4h; pH=7; Reagent/catalyst; Enzymatic reaction;

DOI:10.1039/c2dt32429f

upstream raw materials:

8-quinolinol

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

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

hydrogenchloride

Downstream raw materials:

chloroxine

5,7-diiodo-8-hydroxyquinoline

8-((tert-butyldimethylsilyl)oxy)-5-chloro-7-iodoquinoline

5-Chloro-7-(Dimethylphenylsilyl)-8-Quinolinol

Refernces

• 1、 Das,Mukherji. "-". . p. 1111. Retrieved 1957.
• 2、 Motati, Damoder Reddy,Uredi, Dilipkumar,Watkins, E. Blake. "A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines". . p. 1782 - 1788. Retrieved 2018/02/23.
• 3、 Oliveri, Valentina,Viale, Maurizio,Caron, Giulia,Aiello, Cinzia,Gangemi, Rosaria,Vecchio, Graziella. "Glycosylated copper(ii) ionophores as prodrugs for β-glucosidase activation in targeted cancer therapy". . p. 2023 - 2034. Retrieved 2013/03/14.