CAS 130-26-7|Chloroiodoquine|Rheaform|Cliochinolo [dcit]|Rometin|Iodochlorhydroxyquinoline|Alioform|Cliochinolum|Formtone-HC|Chinoformum|Bactol|Dermaform|Enteritan|Hi-eneterol|Cremo-quin|Clioquinolu...

General Information

Structure

Molecular Formula

C₉H₅ClINO

Molecular Mass

305.49957

Exact Mass

304.91043947

Charge

InChI

InChI=1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

InChIKey

QCDFBFJGMNKBDO-UHFFFAOYSA-N

Canonic Smiles

Ic1cc(Cl)c2c(c1O)nccc2

Isomeric Smiles

Ic1c(O)c2ncccc2c(Cl)c1

Calculated Properties

JChem

Acid pKa

7.3377995

H Acceptors

H Donor

LogD (pH = 5.5)

3.3496072

LogD (pH = 7.4)

3.029213

Log P

3.3603244

Molar Refractivity

60.1275

Polarizability

24.570114

Polar Surface Area

33.12

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.66

LOG S

-3.06

Solubility (Water)

2.64e-01 g/l

Data Source

Names and Identifiers

Synonyms

ChloroiodoquineCliochinolo [dcit]IodochlorhydroxyquinolineClioquinolum [inn-latin]Iodoxyquinoline5-Chloro-7-iodoquinolin-8-olChloroiodoquinIodochlorhydroxyquinIodochloroxyquinolineIodochlorohydroxyquinolineIODOChloro-8-hydroxyiodoquinoline7-Iodo-5-chloro-8-hydroxyquinolineIodochlorohydroxyquin5-Chlor-7-jod-8-hydroxy-chinolin [German]Jodchloroxychinolinum5-Chloro-7-iodo-8-hydroxyquinolineIodochloroxineIodochloroxychinolinum5-Chloro-7-iodo-8-quinolinolIodochlorhydroxyquinolClioquinolCaswell No. 193Iodochloroquine5-Chloro-8-hydroxy-7-iodoquinoline7-Iodo-5-chloroxine5-chloro-7-iodoquinolin-8-olClioquinol5-Chloro-8-hydroxy-7-iodoquinoline5-氯-8-羟基-7-碘喹啉5-氯-7-碘-8-羟基喹啉氯碘喹啉5-Chloro-7-iodo-8-quinolinol氯碘羟喹Clioquinol5-氯-7-碘-8-羟基喹啉氯碘羟喹5-氯-8-羟基-7-碘喹啉Clioqinol5-Chloro-8-hydroxy-7-iodoquinoline

Brand Name

RheaformRometinAlioformCliochinolumFormtone-HCChinoformumBactolDermaformEnteritanHi-eneterolCremo-quinIodenterolLoquinolEnteroquinolEnterovalodonVioformAmebilLekoseptCortinEntrokinOralcerCifoformDomeform-HCQuinoformNioformDioquinolEnterseptolEntero-bio formQuin-o-cremeEczecidinMycoquinRacetQuinambicideEntero-septolChlorojodochinCliquinolEnterozolCorqueIodoenterolEmaformVioform-hydrocortisoneHi-enterolChinoformBudoformEnterum locortenAmoenolAlchloquinCort-quinEnteroseptolHydriodide-enterolEntero-bioformAla-quinVioformioBarquinolDomeformHysoneUad lotionEntero-vioformNystaformEntero-vioformioLidaform-HC

IUPAC name

5-chloro-7-iodoquinolin-8-ol

IUPAC Traditional name

clioquinol

Names and Identifiers

Registration numbers

MDL Number

CAS Number

Beilstein Number

Merck Index

PubChem SID

24860632248549492489302816096779146509081

EC Number

204-984-4

PubChem CID

2788

Registration numbers

Properties

Physical Property

171-174°C

ca 175°C dec.

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

05210217

MP Biomedicals Rare Chemical collection

DrugBank

DB04815

Drug Groups

withdrawn

Description

Clioquinol was withdrawn in 1983 due to neurotoxicity.

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.

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.

References

• 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]

• GHOLZ LM, ARONS WL: PROPHYLAXIS AND THERAPY OF AMEBIASIS AND SHIGELLOSIS WITH IODOCHLORHYDROXYQUIN. Am J Trop Med Hyg. 1964 May;13:396-401. [Pubmed]

• 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]

• 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]

• 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

• [Wikipedia]

• [Drugs.com]

Sigma Aldrich

24880

Packaging
100, 500 g in poly bottle

33931

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Molecule Details

References

PubChem Literature

From Data Sources

• Masters DK, Hopkins AD: Therapeutic trial of four amoebicide regimes in rural Zaire. J Trop Med Hyg. 1979 May;82(5):99-101. Pubmed

• 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

• GHOLZ LM, ARONS WL: PROPHYLAXIS AND THERAPY OF AMEBIASIS AND SHIGELLOSIS WITH IODOCHLORHYDROXYQUIN. Am J Trop Med Hyg. 1964 May;13:396-401. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Brand Name

IUPAC name

5-chloro-7-iodoquinolin-8-ol

IUPAC Traditional name

clioquinol

Registration numbers

MDL Number

CAS Number

Beilstein Number

Merck Index

PubChem SID

24860632248549492489302816096779146509081

EC Number

PubChem CID

Molecule Details

MP Biomedicals Rare Chemical collection

DrugBank

DB04815

Drug Groups

withdrawn

Description

Clioquinol was withdrawn in 1983 due to neurotoxicity.

Indication

Used as a topical antifungal treatment.

Pharmacology

Absorption

References

• GHOLZ LM, ARONS WL: PROPHYLAXIS AND THERAPY OF AMEBIASIS AND SHIGELLOSIS WITH IODOCHLORHYDROXYQUIN. Am J Trop Med Hyg. 1964 May;13:396-401. [Pubmed]

• 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]

• 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

• [Wikipedia]

• [Drugs.com]

Sigma Aldrich

24880

Packaging
100, 500 g in poly bottle

33931

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

References

PubChem Literature

From Data Sources

• Masters DK, Hopkins AD: Therapeutic trial of four amoebicide regimes in rural Zaire. J Trop Med Hyg. 1979 May;82(5):99-101. Pubmed

• 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

• GHOLZ LM, ARONS WL: PROPHYLAXIS AND THERAPY OF AMEBIASIS AND SHIGELLOSIS WITH IODOCHLORHYDROXYQUIN. Am J Trop Med Hyg. 1964 May;13:396-401. Pubmed

Bioactivity

PubChem BioAssay

Properties

Physical Property

171-174°C

ca 175°C dec.

Molecule

ID:4359