Chlorquinaldol

Identification

Generic Name
Chlorquinaldol
DrugBank Accession Number
DB13306
Background

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

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 228.07
Monoisotopic: 226.9904692
Chemical Formula
C10H7Cl2NO
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
  • Chlorchinaldol
  • Chlorquinaldol
  • Chlorquinaldolum
  • Clorquinaldol

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAllergic skin reactionCombination Product in combination with: Difluocortolone (DB09095)•••••••••••••••••
Used in combination to treatSkin infectionsCombination Product in combination with: Difluocortolone (DB09095)•••••••••••••••••
Used in combination to treatSkin inflammationCombination Product in combination with: Difluocortolone (DB09095)•••••••••••••••••
Used in combination for symptomatic treatment ofSkin inflammationCombination Product in combination with: Difluocortolone (DB09095)•••••••••••••••••
Used in combination to treatVaginal atrophy with infectionCombination Product in combination with: Promestriene (DB12487)••••••••••••••••••
Contraindications & Blackbox Warnings
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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

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

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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

Adverse Effects
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Toxicity

Oral LD50 (rat) - 660mg/kg

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
No interactions found.

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
IMPETEX %0.1 + %1 KREM, 10 GChlorquinaldol (1 %) + Difluocortolone valerate (0.1 %)CreamTopicalDeva Holding A.S.2009-10-14Not applicableTurkey flag
NERISONA COMBIChlorquinaldol (1 % w/w) + Difluocortolone valerate (0.1 % w/w)CreamTopicalBayer Indonesia2017-12-192022-07-27Indonesia flag
NERISONA-C %0,1 + %1 KREM, 10 GRChlorquinaldol (1 %) + Difluocortolone valerate (0.1 %)CreamTopicalABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
NERISONA-C %0,1 + %1 KREM, 15 GRChlorquinaldol (1 %) + Difluocortolone valerate (0.1 %)CreamTopicalABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş.2020-05-22Not applicableTurkey flag
NERISONA-C %0,1 + %1 KREM, 30 GRChlorquinaldol (1 %) + Difluocortolone valerate (0.1 %)CreamTopicalABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
P01AA04 — ChlorquinaldolR02AA11 — ChlorquinaldolG01AC03 — ChlorquinaldolD08AH02 — Chlorquinaldol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
8-hydroxyquinoline / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Chloroquinoline / Heteroaromatic compound / Hydrocarbon derivative / Methylpyridine
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, monohydroxyquinoline (CHEBI:74500)
Affected organisms
  • Gram negative and gram positive bacteria

Chemical Identifiers

UNII
D6VHC87LLS
CAS number
72-80-0
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

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. [Article]
  2. Degen PH, Moppert J, Schmid K, Weirich EG: Percutaneous absorption of chlorquinaldol (Sterosan). Dermatologica. 1979;159(3):239-44. [Article]
  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. [Article]
  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. [Article]
  5. Sterosan Marketing Article [File]
  6. EMA Approved Product List Chlorquinaldol [File]
KEGG Drug
D07208
ChemSpider
6062
BindingDB
76302
RxNav
2407
ChEBI
74500
ChEMBL
CHEMBL224325
ZINC
ZINC000000119403
Wikipedia
Chlorquinaldol
MSDS
Download (44 KB)

Clinical Trials

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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4TerminatedTreatmentBacterial Vaginosis (BV)1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CreamCutaneous
KitCutaneous
CreamTopical
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/MSsplash10-004i-0090000000-76930f3a7e51b97d3d8f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-cee3d36b18d23163e5d3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-73846f860bbdba6c4160
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1090000000-cddf5c4e5c449c536220
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-4900000000-597349f7f11ce79dfe58
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-8900000000-5b35780a73f382a14dfc
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-140.18773
predicted
DeepCCS 1.0 (2019)
[M+H]+142.54604
predicted
DeepCCS 1.0 (2019)
[M+Na]+149.73576
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:39 / Updated at February 21, 2021 18:54