Chlorquinaldol

Identification

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Name
Chlorquinaldol
Accession Number
DB13306
Type
Small Molecule
Groups
Approved
Description

Chlorquinaldol was used historically as a topical antiseptic under the trade name Sterosan.5 It was marketed in the 1950s as an iodine-free alternative which was also unrelated to sulfa drugs or hormones. Chlorquinaldol is currently approved by the European Medicines Agency as a combination tablet with promestriene for the treatment of bacterial vaginosis.6

Structure
Thumb
Synonyms
  • 2-methyl-5,7-dichloro-8-hydroxyquinoline
  • 5,7-dichloro-2-methyl-8-hydroxyquinoline
  • 5,7-dichloro-2-methyl-8-quinolinol
  • 5,7-dichloro-8-hydroxy-2-methylquinoline
  • 5,7-dichloro-8-hydroxyquinaldine
  • 5,7-dichloro-8-quinaldinol
  • Chlorquinaldol
  • Chlorquinaldolum
  • Clorquinaldol
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
T.R.U.E. Test Thin-Layer Rapid Use Patch TestChlorquinaldol (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) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamaldehyde (41 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 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)KitCutaneousSmartPractice Denmark ApS2012-03-01Not applicableUs
Categories
UNII
D6VHC87LLS
CAS number
72-80-0
Weight
Average: 228.07
Monoisotopic: 226.9904692
Chemical Formula
C10H7Cl2NO
InChI Key
GPTXWRGISTZRIO-UHFFFAOYSA-N
InChI
InChI=1S/C10H7Cl2NO/c1-5-2-3-6-7(11)4-8(12)10(14)9(6)13-5/h2-4,14H,1H3
IUPAC Name
5,7-dichloro-2-methylquinolin-8-ol
SMILES
CC1=NC2=C(C=C1)C(Cl)=CC(Cl)=C2O

Pharmacology

Indication

Chlorquinaldol was used historically as a topical antiseptic agent for skin infections.5 It maintains use in European countries as a combination vaginal tablet with promestriene for use in the treatment of vaginal infections.6

Associated Conditions
Pharmacodynamics

Chlorquinaldol is bacteriocidal in both gram positive and gram negative bacteria. It is more effective in targeting gram positive bacteria, particularly staphylococci.1

Mechanism of action

The mechanism by which Chlorquinaldol exerts it's bacteriocidal effect is unknown. 8-hydroxyquinolines are known to be bidentate chelators of several metal ions which act as critical enzyme cofactors.3 However, the addition of exogenous metal ions does not appear to alter the minimum inhibitory concentration for mycobacterium tuberculosis suggesting that the primary mechanism does not rely on chelation.4

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

There is a high degree of variability in the extent of absorption of topically applied chorquinaldol preparations.2 It is reported to be between 4.2 and 23.5% of the applied dose. This is quite low compared to orally administered preparations which displayed 67.6% absorption in the same study.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

98% of drug is converted to the sulfate form and renally excreted. 2

Route of elimination

Chlorquinadol is primarily excreted in the urine as the sulfate form. 2 About 2% is excreted as the parent drug.

Half life
Not Available
Clearance
Not Available
Toxicity

Oral LD50 (rat) - 660mg/kg

Affected organisms
  • Gram negative and gram positive bacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
  1. Bortolin M, Bidossi A, De Vecchi E, Avveniente M, Drago L: In vitro Antimicrobial Activity of Chlorquinaldol against Microorganisms Responsible for Skin and Soft Tissue Infections: Comparative Evaluation with Gentamicin and Fusidic Acid. Front Microbiol. 2017 Jun 8;8:1039. doi: 10.3389/fmicb.2017.01039. eCollection 2017. [PubMed:28642751]
  2. Degen PH, Moppert J, Schmid K, Weirich EG: Percutaneous absorption of chlorquinaldol (Sterosan). Dermatologica. 1979;159(3):239-44. [PubMed:478062]
  3. Prachayasittikul V, Prachayasittikul S, Ruchirawat S, Prachayasittikul V: 8-Hydroxyquinolines: a review of their metal chelating properties and medicinal applications. Drug Des Devel Ther. 2013 Oct 4;7:1157-78. doi: 10.2147/DDDT.S49763. eCollection 2013. [PubMed:24115839]
  4. Darby CM, Nathan CF: Killing of non-replicating Mycobacterium tuberculosis by 8-hydroxyquinoline. J Antimicrob Chemother. 2010 Jul;65(7):1424-7. doi: 10.1093/jac/dkq145. Epub 2010 Apr 30. [PubMed:20435781]
  5. Sterosan Marketing Article [File]
  6. EMA Approved Product List Chlorquinaldol [File]
External Links
KEGG Drug
D07208
ChemSpider
6062
BindingDB
76302
ChEBI
74500
ChEMBL
CHEMBL224325
Wikipedia
Chlorquinaldol
ATC Codes
P01AA04 — ChlorquinaldolR02AA11 — ChlorquinaldolG01AC03 — ChlorquinaldolD08AH02 — Chlorquinaldol
MSDS
Download (44 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4TerminatedTreatmentBacterial Vaginosis (BV)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
KitCutaneous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)108-112MSDS
Predicted Properties
PropertyValueSource
Water Solubility0.0538 mg/mLALOGPS
logP3.82ALOGPS
logP3.17ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.16 m3·mol-1ChemAxon
Polarizability21.62 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
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

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 / Methylpyridines / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organochlorides
show 1 more
Substituents
Chloroquinoline / 8-hydroxyquinoline / Methylpyridine / Aryl chloride / Aryl halide / Pyridine / Benzenoid / Heteroaromatic compound / Azacycle / Organic nitrogen compound
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, monohydroxyquinoline (CHEBI:74500)

Drug created on June 23, 2017 14:39 / Updated on November 02, 2019 03:10