Chloroxine

Identification

Name
Chloroxine
Accession Number
DB01243  (APRD00866)
Type
Small Molecule
Groups
Approved
Description

Chloroxine is a synthetic antibacterial compound. Chloroxine is a compound used in some shampoos for the treatment of dandruff and seborrheic dermatitis of the scalp.

Structure
Thumb
Synonyms
  • 5,7-Dichlor-8-hydroxychinolin
  • 5,7-Dichloro-8-hydroxyquinoline
  • 5,7-Dichloro-8-oxyquinoline
  • 5,7-Dichloro-8-quinolinol
  • 5,7-Dichlorooxine
  • 5,7-Dichloroxine
  • Chlorquinol
  • CHQ
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CapitrolShampoo20 mg/1gTopicalBristol Myers Squibb Pharma Company2009-06-012012-10-15Us
International/Other Brands
Capitrol / Endiaron
Categories
UNII
2I8BD50I8B
CAS number
773-76-2
Weight
Average: 214.048
Monoisotopic: 212.974819201
Chemical Formula
C9H5Cl2NO
InChI Key
WDFKMLRRRCGAKS-UHFFFAOYSA-N
InChI
InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
IUPAC Name
5,7-dichloroquinolin-8-ol
SMILES
OC1=C(Cl)C=C(Cl)C2=C1N=CC=C2

Pharmacology

Indication

Used in the treatment of dandruff and mild to moderately severe seborrheic dermatitis of the scalp.

Pharmacodynamics

Chloroxine has an antibacterial action, inhibiting the growth of gram-positive as well as some gram-negative organisms. Also, chloroxine has shown some antifungal activity against certain dermatophytes and yeasts.

Mechanism of action

Although the mechanism of action is not understood, chloroxine may slow down mitotic activity in the epidermis, thereby reducing excessive scaling associated with dandruff or seborrheic dermatitis of the scalp. Chloroxine induces SOS-DNA repair in E. coli, so chloroxine may be genotoxic to bacteria.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

The toxicological properties of this material have not been investigated.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Chloroxine.
AmrinoneThe therapeutic efficacy of Chloroxine can be increased when used in combination with Amrinone.
AzimilideThe therapeutic efficacy of Chloroxine can be increased when used in combination with Azimilide.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Chloroxine.
BuspironeThe metabolism of Buspirone can be decreased when combined with Chloroxine.
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Chloroxine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Chloroxine.
DidanosineDidanosine can cause a decrease in the absorption of Chloroxine resulting in a reduced serum concentration and potentially a decrease in efficacy.
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Chloroxine.
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Chloroxine.
Food Interactions
Not Available

References

General References
  1. Malaveille C, Brun G, Bartsch H: Genotoxicity of ochratoxin A and structurally related compounds in Escherichia coli strains: studies on their mode of action. IARC Sci Publ. 1991;(115):261-6. [PubMed:1820340]
  2. Malaveille C, Brun G, Bartsch H: Structure-activity studies in E. coli strains on ochratoxin A (OTA) and its analogues implicate a genotoxic free radical and a cytotoxic thiol derivative as reactive metabolites. Mutat Res. 1994 May 1;307(1):141-7. [PubMed:7513790]
External Links
Human Metabolome Database
HMDB0015373
PubChem Compound
2722
PubChem Substance
46508620
ChemSpider
2621
BindingDB
32187
ChEBI
59477
ChEMBL
CHEMBL1200596
PharmGKB
PA164754879
Drugs.com
Drugs.com Drug Page
Wikipedia
Chloroxine
MSDS
Download (61.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Contract Pharm
Dosage forms
FormRouteStrength
ShampooTopical20 mg/1g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)179.5 °CPhysProp
logP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.138 mg/mLALOGPS
logP3.44ALOGPS
logP3.04ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.95ChemAxon
pKa (Strongest Basic)3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.57 m3·mol-1ChemAxon
Polarizability19.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.9817
Caco-2 permeable+0.7378
P-glycoprotein substrateNon-substrate0.7232
P-glycoprotein inhibitor INon-inhibitor0.9655
P-glycoprotein inhibitor IINon-inhibitor0.9471
Renal organic cation transporterNon-inhibitor0.8087
CYP450 2C9 substrateNon-substrate0.759
CYP450 2D6 substrateNon-substrate0.7206
CYP450 3A4 substrateNon-substrate0.592
CYP450 1A2 substrateInhibitor0.8973
CYP450 2C9 inhibitorNon-inhibitor0.8853
CYP450 2D6 inhibitorNon-inhibitor0.9131
CYP450 2C19 inhibitorNon-inhibitor0.7778
CYP450 3A4 inhibitorNon-inhibitor0.9473
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6649
Ames testNon AMES toxic0.9244
CarcinogenicityNon-carcinogens0.9514
BiodegradationNot ready biodegradable0.9771
Rat acute toxicity2.2486 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8542
hERG inhibition (predictor II)Non-inhibitor0.8636
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.58 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xr-0390000000-37c6d6830bd09ef8b180
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xr-2790000000-123a4bb6fd1928cb1de5

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 / Pyridines and derivatives / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organochlorides
show 1 more
Substituents
8-hydroxyquinoline / Chloroquinoline / Aryl chloride / Aryl halide / Pyridine / Benzenoid / Heteroaromatic compound / Azacycle / Hydrocarbon derivative / Organopnictogen compound
show 7 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, monohydroxyquinoline (CHEBI:59477)

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 04:34