Clioquinol
Identification
- Name
- Clioquinol
- Accession Number
- DB04815
- Description
Clioquinol was withdrawn in 1983 due to neurotoxicity.
- Type
- Small Molecule
- Groups
- Approved, Vet approved, Withdrawn
- Structure
Structure for Clioquinol (DB04815)
- Weight
- Average: 305.5
Monoisotopic: 304.910434914 - Chemical Formula
- C9H5ClINO
- Synonyms
- 5-Chlor-7-jod-8-hydroxy-chinolin
- 5-Chloro-7-iodo-8-hydroxyquinoline
- 5-Chloro-7-iodo-8-quinolinol
- 5-chloro-7-iodoquinolin-8-ol
- 5-Chloro-8-hydroxy-7-iodoquinoline
- 7-Iodo-5-chloro-8-hydroxyquinoline
- 7-Iodo-5-chloroxine
- Chloroiodoquin
- Clioquinol
- Clioquinolum
- Iodochlorhydroxyquin
- Iodochlorhydroxyquinoline
- Iodochlorohydroxyquin
- Iodochloroxyquinoline
- External IDs
- Caswell No. 193
Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
Used as a topical antifungal treatment.
- Associated Conditions
- Acne
- Atopic Dermatitis (AD)
- Dermatitis, Contact
- Dermatosis
- Eczema impetiginous
- Eczema of the nuchal nape of the neck
- Folliculitis
- Fungal ear infection caused by Aspergillus niger
- Infantile Eczema
- Inflammatory Reaction
- Intertrigo
- Lichen simplex chronicus
- Moniliasis
- Nummular Dermatitis
- Otitis Externa
- Pruritis of the scroti
- Pruritus Ani
- Pruritus Vulvae
- Pyoderma
- Stasis dermatitis
- Tinea Capitis
- Tinea Corporis
- Tinea Cruris
- Tinea Pedis
- Bacterial dermatoses
- Chronic otitis externa
- Corticosteroid-responsive dermatoses
- Disseminated Neurodermatitis
- Localized Neurodermatitis
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Clioquinol is a broad-spectrum antibacterial with antifungal properties. Application of clioquinol to extensive or eroded areas of the skin may lead to increased protein-bound iodine (PBI) levels within 1 week. In addition, elevated PBI levels may occur when relatively small areas of the skin are treated with clioquinol for more than 1 week.
- Mechanism of action
Clioquinol is bacteriostatic, however, the precise mechanism of its action is unknown.
- Absorption
Topical absorption is rapid and extensive, especially when the skin is covered with an occlusive dressing or if the medication is applied to extensive or eroded areas of the skin. Clioquinol is absorbed through the skin in sufficient amounts to affect thyroid function tests.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vioform 3% Cream Topical Novartis 1951-12-31 1999-08-04 Canada 
Vioform 3% Ointment Topical Novartis 1910-12-31 1999-04-15 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Aristoform R Crm 0.1% Clioquinol (30 mg) + Triamcinolone acetonide (1 mg) Cream Topical Lederle Cyanamid Canada Inc. 1966-12-31 1997-01-29 Canada Dermoscribe Diaper Clioquinol (1 g/100g) + Zinc oxide (15 g/100g) Ointment Topical Dermoscribe Pty Ltd 2015-03-23 Not applicable US 
Dermoscribe Ichybum Clioquinol (1 g/100g) + Hydrocortisone (1 g/100g) Cream Topical Xlma Pty Ltd 2015-03-23 Not applicable US Locacorten Vioform Clioquinol (3 %) + Flumethasone pivalate (.02 %) Ointment Topical Novartis 1968-12-31 1998-05-08 Canada Locacorten Vioform Clioquinol (3 %) + Flumethasone pivalate (0.02 %) Cream Topical Paladin Labs Inc 1968-12-31 Not applicable Canada Locacorten Vioform Eardrops Clioquinol (1 %) + Flumethasone pivalate (0.02 %) Solution / drops Auricular (otic) Paladin Labs Inc 1969-12-31 Not applicable Canada Neo Vagex Clioquinol (50 mg) + Acetarsol (100 mg) + Benzalkonium chloride (2 mg) Tablet Vaginal Neolab Inc 1964-12-31 1997-08-12 Canada Phen-oris - Ont Top Clioquinol (2 %) + Allantoin (1 %) + Phenol (.25 %) Ointment Topical Germiphene Corporation 1998-12-04 2008-07-17 Canada Phenoris Ont Clioquinol (2 %) + Allantoin (1 %) + Phenol (.25 %) Ointment Topical E L Stickley And Co Ltd. 1978-12-31 1998-12-07 Canada PMS-flumethasone-clioquinol Clioquinol (1.0 %) + Flumethasone pivalate (0.02 %) Solution / drops Auricular (otic) Pharmascience Inc Not applicable Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ala Quin Clioquinol (30 mg/1g) + Hydrocortisone (5 mg/1g) Cream Topical Crown Laboratories 1970-08-19 2021-11-30 US Dermasorb AF Complete Kit Clioquinol (30 mg/1g) + Hydrocortisone (5 mg/1g) Kit Crown Laboratories 2013-11-14 2018-01-02 US
Categories
- ATC Codes
- G01AC02 — Clioquinol
- G01AC — Quinoline derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- D09AA — Medicated dressings with antiinfectives
- D09A — MEDICATED DRESSINGS
- D09 — MEDICATED DRESSINGS
- D — DERMATOLOGICALS
- P01AA — Hydroxyquinoline derivatives
- P01A — AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- P01AA — Hydroxyquinoline derivatives
- P01A — AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Anti-Infective Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Antiseptics and Disinfectants
- Cell-mediated Immunity
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Heterocyclic Compounds, Fused-Ring
- Hydroxyquinoline Derivatives
- Hydroxyquinolines
- Increased Histamine Release
- Medicated Dressings
- Medicated Dressings With Antiinfectives
- Miscellaneous Antifungals
- Otologicals
- Quinoline Derivatives
- Quinolines
- Sensory Organs
- Standardized Chemical Allergen
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as chloroquinolines. These are compounds containing a quinoline moiety, which carries one or more chlorine atoms.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Quinolines and derivatives
- Sub Class
- Haloquinolines
- Direct Parent
- Chloroquinolines
- Alternative Parents
- 8-hydroxyquinolines / O-iodophenols / Pyridines and derivatives / Aryl iodides / Aryl chlorides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds show 3 more
- Substituents
- 2-iodophenol / 8-hydroxyquinoline / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Aryl iodide / Azacycle / Benzenoid / Chloroquinoline / Heteroaromatic compound show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organoiodine compound, organochlorine compound, monohydroxyquinoline (CHEBI:74460)
Chemical Identifiers
- UNII
- 7BHQ856EJ5
- CAS number
- 130-26-7
- InChI Key
- QCDFBFJGMNKBDO-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
- IUPAC Name
- 5-chloro-7-iodoquinolin-8-ol
- SMILES
- OC1=C(I)C=C(Cl)C2=C1N=CC=C2
References
- Synthesis Reference
- US641491
- General References
- Rohde W, Mikelens P, Jackson J, Blackman J, Whitcher J, Levinson W: Hydroxyquinolines inhibit ribonucleic acid-dependent deoxyribonucleic acid polymerase and inactivate Rous sarcoma virus and herpes simplex virus. Antimicrob Agents Chemother. 1976 Aug;10(2):234-40. [PubMed:185949]
- GHOLZ LM, ARONS WL: PROPHYLAXIS AND THERAPY OF AMEBIASIS AND SHIGELLOSIS WITH IODOCHLORHYDROXYQUIN. Am J Trop Med Hyg. 1964 May;13:396-401. [PubMed:14162901]
- Kager PA: [Outbreak of amoebiasis in a Dutch family; tropics unexpectedly nearby]. Ned Tijdschr Geneeskd. 2005 Jan 1;149(1):51-2; author reply 52-3. [PubMed:15651505]
- Bosman DK, Benninga MA, van de Berg P, Kooijman GC, van Gool T: [Dientamoeba fragilis: possibly an important cause of persistent abdominal pain in children]. Ned Tijdschr Geneeskd. 2004 Mar 20;148(12):575-9. [PubMed:15074181]
- Masters DK, Hopkins AD: Therapeutic trial of four amoebicide regimes in rural Zaire. J Trop Med Hyg. 1979 May;82(5):99-101. [PubMed:226725]
- TITCK Product Information: Precort-A (desonide/clioquinol) topical ointment [Link]
- External Links
- PubChem Compound
- 2788
- PubChem Substance
- 46509081
- ChemSpider
- 2686
- BindingDB
- 32188
- 5942
- ChEBI
- 74460
- ChEMBL
- CHEMBL497
- ZINC
- ZINC000006409735
- PharmGKB
- PA449039
- PDBe Ligand
- CQL
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Clioquinol
- AHFS Codes
- 84:04.08.92 — Miscellaneous Antifungals
- PDB Entries
- 3kcx
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Dermatitis, Eczematous 1 1 Terminated Treatment Acute Lymphocytic Leukemia (ALL) / Acute Myeloid Leukemia (AML) / Chronic Lymphocytic Leukaemia (CLL) / Lymphoma, Hodgkins / Multiple Myeloma (MM) / Myelodysplasia / Non-Hodgkin's Lymphoma (NHL) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical 0.05 g Cream Topical 0.1 % Ointment Topical 0.1 % Kit Ointment Topical Cream Topical Cream Topical 3 g Solution / drops Auricular (otic) Solution / drops Auricular (otic) 10 MG/ML Cream Topical 0.2 mg/g Cream Topical 0.02 % Emulsion Topical 0.02 % Ointment Topical 0.2 mg/g Ointment Topical 3 % Paste Topical 0.02 % Solution / drops Auricular (otic) 1 % Solution / drops Transmucosal 0.02 % Tablet Vaginal Cream Topical 0.05 mg Cream Topical 0.125 % Ointment Topical 0.125 % Patch Cutaneous Cream Topical Ointment Topical Powder Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178.5 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.264 mg/mL ALOGPS logP 3.66 ALOGPS logP 3.36 ChemAxon logS -3.1 ALOGPS pKa (Strongest Acidic) 7.34 ChemAxon pKa (Strongest Basic) 3.28 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 33.12 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 60.13 m3·mol-1 ChemAxon Polarizability 22.63 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9923 Blood Brain Barrier + 0.9772 Caco-2 permeable + 0.7059 P-glycoprotein substrate Non-substrate 0.7305 P-glycoprotein inhibitor I Non-inhibitor 0.9592 P-glycoprotein inhibitor II Non-inhibitor 0.9551 Renal organic cation transporter Non-inhibitor 0.8203 CYP450 2C9 substrate Non-substrate 0.7366 CYP450 2D6 substrate Non-substrate 0.7321 CYP450 3A4 substrate Non-substrate 0.5901 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.8998 CYP450 3A4 inhibitor Non-inhibitor 0.9321 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6827 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9518 Biodegradation Not ready biodegradable 0.9936 Rat acute toxicity 1.8273 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8234 hERG inhibition (predictor II) Non-inhibitor 0.8777
Spectra
- Mass Spec (NIST)
- Download (8.34 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0udi-2901000000-22ecce16d52e911c9ef0
Drug created on September 11, 2007 20:06 / Updated on March 01, 2021 12:05