Clioquinol

Identification

Name
Clioquinol
Accession Number
DB04815
Type
Small Molecule
Groups
Approved, Vet approved, Withdrawn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Clioquinol was withdrawn in 1983 due to neurotoxicity.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 IDs
Caswell No. 193
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vioform 3%Cream3 %TopicalNovartis1951-12-311999-08-04Canada
Vioform 3%Ointment3 %TopicalNovartis1910-12-311999-04-15Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Aristoform R Crm 0.1%Clioquinol (30 mg) + Triamcinolone acetonide (1 mg)CreamTopicalLederle Cyanamid Canada Inc.1966-12-311997-01-29Canada
Dermoscribe IchybumClioquinol (1 g/100g) + Hydrocortisone (1 g/100g)CreamTopicalXlma Pty Ltd2015-03-23Not applicableUs
Locacorten VioformClioquinol (3 %) + Flumethasone pivalate (.02 %)OintmentTopicalNovartis1968-12-311998-05-08Canada
Locacorten VioformClioquinol (3 %) + Flumethasone pivalate (0.02 %)CreamTopicalPaladin Labs Inc1968-12-31Not applicableCanada
Locacorten Vioform EardropsClioquinol (1 %) + Flumethasone pivalate (0.02 %)Solution / dropsAuricular (otic)Paladin Labs Inc1969-12-31Not applicableCanada
Neo VagexClioquinol (50 mg) + Acetarsol (100 mg) + Benzalkonium chloride (2 mg)TabletVaginalNeolab Inc1964-12-311997-08-12Canada
Phen-oris - Ont TopClioquinol (2 %) + Allantoin (1 %) + Phenol (.25 %)OintmentTopicalGermiphene Corporation1998-12-042008-07-17Canada
Phenoris OntClioquinol (2 %) + Allantoin (1 %) + Phenol (.25 %)OintmentTopicalE L Stickley And Co Ltd.1978-12-311998-12-07Canada
PMS-flumethasone-clioquinolClioquinol (1.0 %) + Flumethasone pivalate (0.02 %)Solution / dropsAuricular (otic)Pharmascience IncNot applicableNot applicableCanada
T.R.U.E. Test Thin-Layer Rapid Use Patch TestClioquinol (77 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bromothalonil (4 ug/48h) + Bronopol (203 ug/48h) + Budesonide (0.8 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamaldehyde (41 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb Zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Eugenol (41 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Geraniol (81 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Isoeugenol (17 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylchloroisothiazolinone (3 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + P-Tert-Butylphenol-Formaldehyde Resin (Low Molecular Weight) (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc Dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h)KitSmartPractice Denmark ApS2012-03-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ala QuinClioquinol (30 mg/1g) + Hydrocortisone (5 mg/1g)CreamTopicalCrown Laboratories1970-08-19Not applicableUs
Dermasorb AF Complete KitClioquinol (30 mg/1g) + Hydrocortisone (5 mg/1g)KitTopicalCrown Laboratories2013-11-142018-01-02Us
Categories
UNII
7BHQ856EJ5
CAS number
130-26-7
Weight
Average: 305.5
Monoisotopic: 304.910434914
Chemical Formula
C9H5ClINO
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

Pharmacology

Indication

Used as a topical antifungal treatment.

Associated Conditions
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [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
PubChem Compound
2788
PubChem Substance
46509081
ChemSpider
2686
BindingDB
32188
ChEBI
74460
ChEMBL
CHEMBL497
PharmGKB
PA449039
HET
CQL
Drugs.com
Drugs.com Drug Page
Wikipedia
Clioquinol
ATC Codes
G01AC02 — ClioquinolD09AA10 — ClioquinolD08AH30 — ClioquinolP01AA52 — Clioquinol, combinationsP01AA02 — ClioquinolS02AA05 — Clioquinol
AHFS Codes
  • 84:04.08.92 — Miscellaneous Antifungals
PDB Entries
3kcx

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentAcute Lymphocytic Leukemia (ALL) / Chronic Lymphocytic Leukaemia (CLL) / Leukemia Acute Myeloid Leukemia (AML) / Lymphoma, Hodgkins / Multiple Myeloma (MM) / Myelodysplasia / Non-Hodgkin's Lymphoma (NHL)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
KitTopical
CreamTopical
OintmentTopical
Solution / dropsAuricular (otic)
TabletVaginal
Kit
CreamTopical3 %
OintmentTopical3 %
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

Taxonomy

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
Chloroquinoline / 8-hydroxyquinoline / 2-iodophenol / Aryl chloride / Aryl halide / Aryl iodide / Pyridine / Benzenoid / Heteroaromatic compound / Azacycle
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organoiodine compound, organochlorine compound, monohydroxyquinoline (CHEBI:74460)

Drug created on September 11, 2007 14:06 / Updated on October 16, 2018 08:37