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Identification
NameClioquinol
Accession NumberDB04815
TypeSmall Molecule
GroupsVet Approved, Withdrawn
Description

Clioquinol was withdrawn in 1983 due to neurotoxicity.

Structure
Thumb
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
Clioquinolum
Iodochlorhydroxyquin
Iodochlorhydroxyquinoline
Iodochlorohydroxyquin
Iodochloroxyquinoline
External Identifiers
  • Caswell No. 193
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vioform 3%cream3 %topicalNovartis Pharmaceuticals Canada Inc1951-12-311999-08-04Canada
Vioform 3%ointment3 %topicalNovartis Pharmaceuticals Canada Inc1910-12-311999-04-15Canada
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Ala QuinCrown Laboratories
Aristoform R Crm 0.1%Lederle Cyanamid Canada Inc.
Dermoscribe IchybumXlma Pty Ltd
Locacorten VioformPaladin Labs Inc
Locacorten Vioform EardropsPaladin Labs Inc
Phen-oris - Ont TopGermiphene Corporation
Phenoris OntE L Stickley And Co Ltd.
PMS-flumethasone-clioquinolPharmascience Inc
Vioform + HydrocortisoneCiba Pharmaceuticals, Ciba Geigy Canada Ltd.
Vioform HydrocortisonePaladin Labs Inc
Vioform Hydrocortisone MildNovartis Pharmaceuticals Canada Inc
SaltsNot Available
Categories
UNII7BHQ856EJ5
CAS number130-26-7
WeightAverage: 305.5
Monoisotopic: 304.910434914
Chemical FormulaC9H5ClINO
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyquinolines. These are compounds containing a quinoline moiety bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassHydroxyquinolines
Direct ParentHydroxyquinolines
Alternative Parents
Substituents
  • Chloroquinoline
  • 8-hydroxyquinoline
  • Hydroxyquinoline
  • 2-iodophenol
  • 2-halophenol
  • 4-halophenol
  • Iodobenzene
  • Chlorobenzene
  • Benzenoid
  • Pyridine
  • Aryl iodide
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed as a topical antifungal treatment.
PharmacodynamicsClioquinol 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 actionClioquinol is bacteriostatic, however, the precise mechanism of its action is unknown.
Related Articles
AbsorptionTopical 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 distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Creamtopical
Ointmenttopical
Dropsotic
Creamtopical3 %
Ointmenttopical3 %
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point178.5 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.34 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

DrugSyn.org

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. [PubMed:185949 ]
  2. 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 ]
  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. [PubMed:15651505 ]
  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. [PubMed:15074181 ]
  5. 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 ]
External Links
ATC CodesG01AC02D09AA10D08AH30P01AA52P01AA02S02AA05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on September 11, 2007 14:06 / Updated on August 17, 2016 12:24