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Showing drug card for Clioquinol (DB04815)

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Version 2.5
Creation Date 2007-09-11 20:06:26
Update Date 2008-08-26 14:29:18
Primary Accession Number DB04815
Secondary Accession Number Not Available
Name Clioquinol
Drug Type
  • Small Molecule
  • Withdrawn
Description Clioquinol was withdrawn in 1983 due to neurotoxicity.
Synonyms
  1. 5-Chlor-7-jod-8-hydroxy-chinolin [German]
  2. 5-Chloro-7-iodo-8-hydroxyquinoline
  3. 5-Chloro-7-iodo-8-quinolinol
  4. 5-Chloro-7-iodoquinolin-8-ol
  5. 5-Chloro-8-hydroxy-7-iodoquinoline
  6. 7-Iodo-5-chloro-8-hydroxyquinoline
  7. 7-Iodo-5-chloroxine
  8. Caswell No. 193
  9. Chloro-8-hydroxyiodoquinoline
  10. Chloroiodoquin
  11. Chloroiodoquine
  12. Cliochinolo [dcit]
  13. Clioquinolum [inn-latin]
  14. IODO
  15. Iodochlorhydroxyquin
  16. Iodochlorhydroxyquinol
  17. Iodochlorhydroxyquinoline
  18. Iodochlorohydroxyquin
  19. Iodochlorohydroxyquinoline
  20. Iodochloroquine
  21. Iodochloroxine
  22. Iodochloroxychinolinum
  23. Iodochloroxyquinoline
  24. Iodoxyquinoline
  25. Jodchloroxychinolinum
Brand Names
  1. Ala-quin
  2. Alchloquin
  3. Alioform
  4. Amebil
  5. Amoenol
  6. Bactol
  7. Barquinol
  8. Budoform
  9. Chinoform
  10. Chinoformum
  11. Chlorojodochin
  12. Cifoform
  13. Cliochinolum
  14. Cliquinol
  15. Corque
  16. Cort-quin
  17. Cortin
  18. Cremo-quin
  19. Dermaform
  20. Dioquinol
  21. Domeform
  22. Domeform-HC
  23. Eczecidin
  24. Emaform
  25. Enteritan
  26. Entero-bio form
  27. Entero-bioform
  28. Entero-septol
  29. Entero-vioform
  30. Entero-vioformio
  31. Enteroquinol
  32. Enteroseptol
  33. Enterovalodon
  34. Enterozol
  35. Enterseptol
  36. Enterum locorten
  37. Entrokin
  38. Formtone-HC
  39. Hi-eneterol
  40. Hi-enterol
  41. Hydriodide-enterol
  42. Hysone
  43. Iodenterol
  44. Iodoenterol
  45. Lekosept
  46. Lidaform-HC
  47. Loquinol
  48. Mycoquin
  49. Nioform
  50. Nystaform
  51. Oralcer
  52. Quin-o-creme
  53. Quinambicide
  54. Quinoform
  55. Racet
  56. Rheaform
  57. Rometin
  58. Uad lotion
  59. Vioform
  60. Vioform-hydrocortisone
  61. Vioformio
Brand Mixtures Not Available
Chemical IUPAC Name 5-chloro-7-iodoquinolin-8-ol
Chemical Formula C9H5ClINO
Chemical Structure Structure
CAS Registry Number 130-26-7
InChI Identifier InChI=1/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
InChI Key QCDFBFJGMNKBDO-UHFFFAOYAT
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 2788 Link Image
PubChem Substance 10475089 Link Image
ChEBI ID Not Available
PharmGKB ID PA449039 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00074454 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Clioquinol Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 305.5000
Monoisotopic Molecular Weight 304.9104
State Solid
Melting Point 178.5 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.64e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP 3.66 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.06 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES OC1=C(I)C=C(Cl)C2=C1N=CC=C2
Canonical SMILES OC1=C(I)C=C(Cl)C2=C1N=CC=C2
Drug Category
  • Antifungal Agents
ATC Codes Not Available
AHFS Codes Not Available
Indication Used as a topical antifungal treatment.
Pharmacology 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.
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. GHOLZ LM, ARONS WL: PROPHYLAXIS AND THERAPY OF AMEBIASIS AND SHIGELLOSIS WITH IODOCHLORHYDROXYQUIN. Am J Trop Med Hyg. 1964 May;13:396-401. [PubMed Link Image]
  2. 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 Link Image]
  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 Link Image]
  4. 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 Link Image]
  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 Link Image]
  6. Wikipedia Link Image
Organisms Affected Not Available

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.