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Identification
NameClioquinol
Accession NumberDB04815
Typesmall molecule
Groupswithdrawn
Description

Clioquinol was withdrawn in 1983 due to neurotoxicity.

Structure
Thumb
Synonyms
SynonymLanguageCode
5-Chlor-7-jod-8-hydroxy-chinolinGermanNot Available
5-Chloro-7-iodo-8-hydroxyquinolineNot AvailableNot Available
5-Chloro-7-iodo-8-quinolinolNot AvailableNot Available
5-chloro-7-iodoquinolin-8-olNot AvailableNot Available
5-Chloro-8-hydroxy-7-iodoquinolineNot AvailableNot Available
7-Iodo-5-chloro-8-hydroxyquinolineNot AvailableNot Available
7-Iodo-5-chloroxineNot AvailableNot Available
ChloroiodoquinNot AvailableNot Available
ClioquinolumLatinINN
IodochlorhydroxyquinNot AvailableNot Available
IodochlorhydroxyquinolineNot AvailableNot Available
IodochlorohydroxyquinNot AvailableNot Available
IodochloroxyquinolineNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixtures
Brand NameIngredients
Vioformclioquinol + hydrocortisone
CategoriesNot Available
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
Mass Specshow(8.34 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassQuinolines and Derivatives
SubclassHydroxyquinolines
Direct parentHydroxyquinolines
Alternative parentsp-Chlorophenols; o-Iodophenols; Chlorobenzenes; Iodobenzenes; Aryl Iodides; Pyridines and Derivatives; Aryl Chlorides; Enols; Polyamines; Organoiodides; Organochlorides
Substituents4-chlorophenol; 2-iodophenol; 2-halophenol; 4-halophenol; phenol derivative; iodobenzene; chlorobenzene; aryl halide; aryl iodide; pyridine; benzene; aryl chloride; polyamine; enol; organoiodide; organonitrogen compound; organochloride; organohalogen
Classification descriptionThis compound belongs to the hydroxyquinolines. These are compounds containing a quinoline moiety bearing an hydroxyl group.
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.
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
Metabolism
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
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.8998
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point178.5 °CPhysProp
Predicted Properties
PropertyValueSource
water solubility2.64e-01 g/lALOGPS
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 area33.12ChemAxon
rotatable bond count0ChemAxon
refractivity60.13ChemAxon
polarizability22.63ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US641491
General Reference
  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
  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
  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
  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
  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
External Links
ResourceLink
PubChem Compound2788
PubChem Substance46509081
ChemSpider2686
PharmGKBPA449039
Drug Product Database74454
Drugs.comhttp://www.drugs.com/mtm/clioquinol-topical.html
WikipediaClioquinol
ATC CodesP01AA02D08AH30S02AA05G01AC02D09AA10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
Drug created on September 11, 2007 14:06 / Updated on October 08, 2013 14:22