5-chloro-7-iodoquinolin-8-ol

• ChemBase ID: 4359
• Molecular Formular: C9H5ClINO
• Molecular Mass: 305.49957
• Monoisotopic Mass: 304.91043947
• SMILES: Ic1c(O)c2ncccc2c(Cl)c1
• Canonical SMILES: Ic1cc(Cl)c2c(c1O)nccc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-7-iodoquinolin-8-ol
• IUPAC Traditional name: clioquinol
• Brand Name: 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
• Synonyms: Clioqinol; 5-Chloro-8-hydroxy-7-iodoquinoline; 5-Chlor-7-jod-8-hydroxy-chinolin [German]; 5-Chloro-7-iodo-8-quinolinol; 5-Chloro-7-iodo-8-hydroxyquinoline; 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; Clioquinolum [inn-latin]; Cliochinolo [dcit]; Iodoxyquinoline; Jodchloroxychinolinum; Iodochloroxyquinoline; Iodochloroxychinolinum; Iodochloroxine; Iodochloroquine; Iodochlorohydroxyquinoline; Iodochlorohydroxyquin; Iodochlorhydroxyquinoline; Iodochlorhydroxyquinol; Iodochlorhydroxyquin; IODO; Chloroiodoquin; Chloroiodoquine; Clioquinol; Clioquinol; 5-Chloro-8-hydroxy-7-iodoquinoline; 5-Chloro-7-iodo-8-quinolinol; 5-chloro-7-iodoquinolin-8-ol; Clioquinol; 5-氯-8-羟基-7-碘喹啉; 5-氯-8-羟基-7-碘喹啉; 氯碘喹啉; 氯碘羟喹; 5-氯-7-碘-8-羟基喹啉; 5-氯-7-碘-8-羟基喹啉; 氯碘羟喹

Database IDs

• CAS Number: 130-26-7
• EC Number: 204-984-4
• MDL Number: MFCD00006787
• Beilstein Number: 153637
• Merck Index: 145031
• PubChem SID: 46509081; 160967791; 24860632; 24854949; 24893028
• PubChem CID: 2788

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.3377995
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.3496072
• LogD (pH = 7.4): 3.029213
• Log P: 3.3603244
• Molar Refractivity: 60.1275 cm^3
• Polarizability: 24.570114 Å^3
• Polar Surface Area: 33.12 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.66
• LOG S: -3.06
• Solubility (Water): 2.64e-01 g/l

PROPERTIES

Physical Property

• Melting Point: 171-174°C; ca 175°C dec.

Safety Information

• Storage Warning: Harmful
• RTECS: VC5075000
• European Hazard Symbols: Toxic (T); X
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25; 42/43-63; R:25
• Safety Statements: 22-24-37-45; 36/37/39-45; S:28-36/37/39-45-53
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301; H334-H317-H361
• GHS Precautionary statements: P285-P261-P302+P352-P321-P405-P501A; P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); 97%; 98%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C9H5ClINO

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

Sigma Aldrich - 33931

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

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