Identification
- Summary
Clioquinol is an antifungal cream used to treat a variety of fungal infections.
- Brand Names
- Locacorten Vioform
- Generic Name
- Clioquinol
- DrugBank Accession Number
- DB04815
- Background
Clioquinol was withdrawn in 1983 due to neurotoxicity.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- Approved, Vet approved, Withdrawn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
- Indication
Used as a topical antifungal treatment.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Acne Combination Product in combination with: Hydrocortisone (DB00741) •••••••••••• •••••• •••••••• Used in combination to treat Acne Combination Product in combination with: Hydrocortisone (DB00741) •••••••••••• •••••• •••••••• Used in combination to treat Atopic dermatitis Combination Product in combination with: Hydrocortisone (DB00741) •••••••••••• •••••• •••••••• Used in combination to treat Atopic dermatitis Combination Product in combination with: Hydrocortisone (DB00741) •••••••••••• •••••• •••••••• Used in combination to treat Contact dermatitis Combination Product in combination with: Hydrocortisone (DB00741) •••••••••••• •••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vioform 3% Ointment 3 % Topical Novartis 1910-12-31 1999-04-15 Canada 
Vioform 3% Cream 3 % Topical Novartis 1951-12-31 1999-08-04 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Aristoform R Crm 0.1% Clioquinol (30 mg / g) + Triamcinolone acetonide (1 mg / g) Cream Topical Lederle Cyanamid Canada Inc. 1966-12-31 1997-01-29 Canada BETAGEN CREMA TOPICA Clioquinol (3 g) + Betamethasone valerate (0.05 g) + Gentamicin sulfate (0.1 g) Cream Topical COASPHARMA S.A.S. 2007-02-26 2009-08-26 Colombia 
BETNOVATE-C % 0,1 + % 3 KREM, 15 GR Clioquinol (3 %) + Betamethasone (0.1 %) Cream Topical GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
BETNOVATE-C % 0,1 + % 3 KREM, 30 GR Clioquinol (3 %) + Betamethasone (0.1 %) Cream Topical GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş. 1968-09-28 Not applicable Turkey BETNOVATE-C % 0,1 + % 3 KREM, 5 GR Clioquinol (3 %) + Betamethasone (0.1 %) Cream Topical GLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey - 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)
- Affected organisms
- Not Available
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. [Article]
- GHOLZ LM, ARONS WL: PROPHYLAXIS AND THERAPY OF AMEBIASIS AND SHIGELLOSIS WITH IODOCHLORHYDROXYQUIN. Am J Trop Med Hyg. 1964 May;13:396-401. [Article]
- 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. [Article]
- 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. [Article]
- Masters DK, Hopkins AD: Therapeutic trial of four amoebicide regimes in rural Zaire. J Trop Med Hyg. 1979 May;82(5):99-101. [Article]
- 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
- PDB Entries
- 3kcx
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Atopic Dermatitis 1 2 Active Not Recruiting Treatment Epilepsy, Intractable 1 1 Terminated Treatment Acute Lymphoblastic Leukemia (ALL) / Acute Myeloid Leukemia / Chronic Lymphocytic Leukemia / Hodgkin's Lymphoma / Multiple Myeloma (MM) / Myelodysplastic Syndrome / Non-Hodgkin's Lymphoma (NHL) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Cutaneous Cream Cutaneous 3.000 g Kit Ointment Topical Cream Topical Solution / drops Auricular (otic) Emulsion Topical Paste Topical Solution / drops Transmucosal Tablet Vaginal Kit Cutaneous Gel Topical Cream Topical 3 % Ointment Topical 3 % 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 -1 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 146.52675 predictedDeepCCS 1.0 (2019) [M+H]+ 149.32388 predictedDeepCCS 1.0 (2019) [M+Na]+ 158.60698 predictedDeepCCS 1.0 (2019)
Drug created at September 11, 2007 20:06 / Updated at February 20, 2024 23:55