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Identification
Name Clioquinol
Accession Number DB04815
Type small molecule
Groups withdrawn
Description

Clioquinol was withdrawn in 1983 due to neurotoxicity.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • 5-Chlor-7-jod-8-hydroxy-chinolin [German]
  • 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
  • Caswell No. 193
  • Chloro-8-hydroxyiodoquinoline
  • Chloroiodoquin
  • Chloroiodoquine
  • Cliochinolo [dcit]
  • Clioquinolum [inn-latin]
  • IODO
  • Iodochlorhydroxyquin
  • Iodochlorhydroxyquinol
  • Iodochlorhydroxyquinoline
  • Iodochlorohydroxyquin
  • Iodochlorohydroxyquinoline
  • Iodochloroquine
  • Iodochloroxine
  • Iodochloroxychinolinum
  • Iodochloroxyquinoline
  • Iodoxyquinoline
  • Jodchloroxychinolinum
Brand names
  • Ala-quin
  • Alchloquin
  • Alioform
  • Amebil
  • Amoenol
  • Bactol
  • Barquinol
  • Budoform
  • Chinoform
  • Chinoformum
  • Chlorojodochin
  • Cifoform
  • Cliochinolum
  • Cliquinol
  • Corque
  • Cort-quin
  • Cortin
  • Cremo-quin
  • Dermaform
  • Dioquinol
  • Domeform
  • Domeform-HC
  • Eczecidin
  • Emaform
  • Enteritan
  • Entero-bio form
  • Entero-bioform
  • Entero-septol
  • Entero-vioform
  • Entero-vioformio
  • Enteroquinol
  • Enteroseptol
  • Enterovalodon
  • Enterozol
  • Enterseptol
  • Enterum locorten
  • Entrokin
  • Formtone-HC
  • Hi-eneterol
  • Hi-enterol
  • Hydriodide-enterol
  • Hysone
  • Iodenterol
  • Iodoenterol
  • Lekosept
  • Lidaform-HC
  • Loquinol
  • Mycoquin
  • Nioform
  • Nystaform
  • Oralcer
  • Quin-o-creme
  • Quinambicide
  • Quinoform
  • Racet
  • Rheaform
  • Rometin
  • Uad lotion
  • Vioform
  • Vioform-hydrocortisone
  • Vioformio
Brand name mixtures Not Available
Categories
  • Antifungal Agents
CAS number 130-26-7
Weight Average: 305.5
Monoisotopic: 304.910434914
Chemical Formula C9H5ClINO
InChI Key InChIKey=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
Plain Text
IUPAC Name
5-chloro-7-iodoquinolin-8-ol
SMILES
OC1=C(I)C=C(Cl)C2=C1N=CC=C2
Plain Text
Mass Spec show (8.3 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Used as a topical antifungal treatment.
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
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 178.5 oC
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 2.64e-01 g/l ALOGPS
logP 3.66 ALOGPS
logP 3.36 ChemAxon Molconvert
logS -3.06 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 33.12 ChemAxon Molconvert
rotatable bond count 0 ChemAxon Molconvert
refractivity 60.13 ChemAxon Molconvert
polarizability 22.63 ChemAxon Molconvert
References
Synthesis Reference Not Available
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
Resource Link
PubChem Compound 2788 Link_out
PubChem Substance 46509081 Link_out
ChemSpider 2686 Link_out
PharmGKB PA449039 Link_out
Drug Product Database 74454 Link_out
Drugs.com http://www.drugs.com/mtm/clioquinol-topical.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Clioquinol Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Comments
Drug created on September 11, 2007 14:06 / Updated on November 10, 2010 14:57

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.