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
Structure for Chlorquinaldol (DB13306)
- 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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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Allergic skin reaction Combination Product in combination with: Difluocortolone (DB09095) •••••••••••• ••••• Used in combination to treat Skin infections Combination Product in combination with: Difluocortolone (DB09095) •••••••••••• ••••• Used in combination to treat Skin inflammation Combination Product in combination with: Difluocortolone (DB09095) •••••••••••• ••••• Used in combination for symptomatic treatment of Skin inflammation Combination Product in combination with: Difluocortolone (DB09095) •••••••••••• ••••• Used in combination to treat Vaginal atrophy with infection Combination Product in combination with: Promestriene (DB12487) •••••••••••• •••••• - Contraindications & Blackbox Warnings
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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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Oral LD50 (rat) - 660mg/kg
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image IMPETEX %0.1 + %1 KREM, 10 G Chlorquinaldol (1 %) + Difluocortolone valerate (0.1 %) Cream Topical Deva Holding A.S. 2009-10-14 Not applicable Turkey 
NERISONA-C %0,1 + %1 KREM, 10 GR Chlorquinaldol (1 %) + Difluocortolone valerate (0.1 %) Cream Topical ABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey NERISONA-C %0,1 + %1 KREM, 15 GR Chlorquinaldol (1 %) + Difluocortolone valerate (0.1 %) Cream Topical ABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş. 2020-05-22 Not applicable Turkey NERISONA-C %0,1 + %1 KREM, 30 GR Chlorquinaldol (1 %) + Difluocortolone valerate (0.1 %) Cream Topical ABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey T.R.U.E. Test Thin-Layer Rapid Use Patch Test Chlorquinaldol (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) + 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) + p-tert-Butylphenol-formaldehyde resin (low molecular weight) (36 ug/48h) Kit Cutaneous SmartPractice Denmark ApS 2012-03-01 Not applicable US 
Categories
- ATC Codes
- P01AA04 — Chlorquinaldol
- P01AA — Hydroxyquinoline derivatives
- P01A — AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- G01AC — Quinoline derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Antiseptics and Disinfectants
- Cell-mediated Immunity
- Chloroquinolinols
- Dermatologicals
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Heterocyclic Compounds, Fused-Ring
- Hydroxyquinoline Derivatives
- Hydroxyquinolines
- Increased Histamine Release
- Quinoline Derivatives
- Quinolines
- Standardized Chemical Allergen
- Throat Preparations
- 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
- 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]
- Degen PH, Moppert J, Schmid K, Weirich EG: Percutaneous absorption of chlorquinaldol (Sterosan). Dermatologica. 1979;159(3):239-44. [Article]
- 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]
- 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]
- Sterosan Marketing Article [File]
- EMA Approved Product List Chlorquinaldol [File]
- External Links
- KEGG Drug
- D07208
- ChemSpider
- 6062
- BindingDB
- 76302
- 2407
- ChEBI
- 74500
- ChEMBL
- CHEMBL224325
- ZINC
- ZINC000000119403
- Wikipedia
- Chlorquinaldol
- MSDS
- Download (44 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Terminated Treatment Bacterial Vaginosis (BV) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Cutaneous Cream Topical Kit Cutaneous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 108-112 MSDS - Predicted Properties
Property Value Source Water Solubility 0.0538 mg/mL ALOGPS logP 3.82 ALOGPS logP 3.17 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 6.99 Chemaxon pKa (Strongest Basic) 4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 33.12 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 56.16 m3·mol-1 Chemaxon Polarizability 21.62 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-76930f3a7e51b97d3d8f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-cee3d36b18d23163e5d3 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-73846f860bbdba6c4160 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-1090000000-cddf5c4e5c449c536220 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-4900000000-597349f7f11ce79dfe58 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0019-8900000000-5b35780a73f382a14dfc Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 140.18773 predictedDeepCCS 1.0 (2019) [M+H]+ 142.54604 predictedDeepCCS 1.0 (2019) [M+Na]+ 149.73576 predictedDeepCCS 1.0 (2019)
Drug created at June 23, 2017 20:39 / Updated at February 21, 2021 18:54