Clioquinol

Identification

Summary

Clioquinol is an antifungal cream used to treat a variety of fungal infections.

Brand Names
Ala-quin, 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Clioquinol was withdrawn in 1983 due to neurotoxicity.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Approved, Vet approved, Withdrawn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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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
Medicalerrors
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Toxicity

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

Products
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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Vioform 3%Cream3 %TopicalNovartis1951-12-311999-08-04Canada flag
Vioform 3%Ointment3 %TopicalNovartis1910-12-311999-04-15Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Aristoform R Crm 0.1%Clioquinol (30 mg / g) + Triamcinolone acetonide (1 mg / g)CreamTopicalLederle Cyanamid Canada Inc.1966-12-311997-01-29Canada flag
BETNOVATE-C KREM, 15 GRClioquinol (3 %) + Betamethasone (0.1 %)CreamTopicalGLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
BETNOVATE-C KREM, 30 GRClioquinol (3 %) + Betamethasone (0.1 %)CreamTopicalGLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
BETNOVATE-C KREM, 5 GRClioquinol (3 %) + Betamethasone (0.1 %)CreamTopicalGLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
BETNOVATE-C MERHEM, 15 GRClioquinol (3 %) + Betamethasone (0.1 %)OintmentTopicalGLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
BETNOVATE-C MERHEM, 30 GRClioquinol (3 %) + Betamethasone (0.1 %)OintmentTopicalGLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
BETNOVATE-C MERHEM, 5 GRClioquinol (3 %) + Betamethasone (0.1 %)OintmentTopicalGLAXOSMİTHKLİNE İLAÇLARI SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Dermoscribe DiaperClioquinol (1 g/100g) + Zinc oxide (15 g/100g)OintmentTopicalDermoscribe Pty Ltd2015-03-23Not applicableUS flag
Dermoscribe IchybumClioquinol (1 g/100g) + Hydrocortisone (1 g/100g)CreamTopicalXlma Pty Ltd2015-03-23Not applicableUS flag
DESONIDA CLIOQUINOL CREMA.Clioquinol (3 g) + Desonide (0.1 g)CreamTopicalALTEA FARMACEUTICA S.A.2006-11-10Not applicableColombia flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ala QuinClioquinol (30 mg/1g) + Hydrocortisone (5 mg/1g)CreamTopicalCrown Laboratories1970-08-192021-11-30US flag
Dermasorb AF Complete KitClioquinol (30 mg/1g) + Hydrocortisone (5 mg/1g)KitCrown Laboratories2013-11-142018-01-02US flag

Categories

ATC Codes
G01AC02 — ClioquinolS02AA05 — ClioquinolD09AA10 — ClioquinolP01AA02 — ClioquinolP01AA52 — Clioquinol, combinationsD08AH30 — Clioquinol
Drug Categories
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
  1. 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]
  2. GHOLZ LM, ARONS WL: PROPHYLAXIS AND THERAPY OF AMEBIASIS AND SHIGELLOSIS WITH IODOCHLORHYDROXYQUIN. Am J Trop Med Hyg. 1964 May;13:396-401. [Article]
  3. 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]
  4. 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]
  5. Masters DK, Hopkins AD: Therapeutic trial of four amoebicide regimes in rural Zaire. J Trop Med Hyg. 1979 May;82(5):99-101. [Article]
  6. TITCK Product Information: Precort-A (desonide/clioquinol) topical ointment [Link]
PubChem Compound
2788
PubChem Substance
46509081
ChemSpider
2686
BindingDB
32188
RxNav
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
PhaseStatusPurposeConditionsCount
3CompletedTreatmentDermatitis, Eczematous1
1TerminatedTreatmentAcute 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
FormRouteStrength
Kit
OintmentTopical
CreamTopical
EmulsionTopical
PasteTopical
Solution / dropsAuricular (otic)
Solution / dropsTransmucosal
TabletVaginal
PatchCutaneous
CreamTopical3 %
OintmentTopical3 %
PowderTopical
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.264 mg/mLALOGPS
logP3.66ALOGPS
logP3.36ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.34ChemAxon
pKa (Strongest Basic)3.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity60.13 m3·mol-1ChemAxon
Polarizability22.63 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9923
Blood Brain Barrier+0.9772
Caco-2 permeable+0.7059
P-glycoprotein substrateNon-substrate0.7305
P-glycoprotein inhibitor INon-inhibitor0.9592
P-glycoprotein inhibitor IINon-inhibitor0.9551
Renal organic cation transporterNon-inhibitor0.8203
CYP450 2C9 substrateNon-substrate0.7366
CYP450 2D6 substrateNon-substrate0.7321
CYP450 3A4 substrateNon-substrate0.5901
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.8998
CYP450 3A4 inhibitorNon-inhibitor0.9321
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6827
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9518
BiodegradationNot ready biodegradable0.9936
Rat acute toxicity1.8273 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8234
hERG inhibition (predictor II)Non-inhibitor0.8777
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.34 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-2901000000-22ecce16d52e911c9ef0

Drug created on September 11, 2007 20:06 / Updated on June 13, 2021 16:25