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Identification
NameChloroxine
Accession NumberDB01243  (APRD00866)
TypeSmall Molecule
GroupsApproved
DescriptionChloroxine 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CapitrolNot Available
EndiaronNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII2I8BD50I8B
CAS number773-76-2
WeightAverage: 214.048
Monoisotopic: 212.974819201
Chemical FormulaC9H5Cl2NO
InChI KeyWDFKMLRRRCGAKS-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
IndicationUsed in the treatment of dandruff and mild to moderately severe seborrheic dermatitis of the scalp.
Structured Indications Not Available
PharmacodynamicsChloroxine 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 actionAlthough 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityThe toxicological properties of this material have not been investigated.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AmlodipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Chloroxine.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Chloroxine is combined with Amrinone.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Azelnidipine.Approved
AzimilideThe risk or severity of adverse effects can be increased when Chloroxine is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Barnidipine.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Chloroxine.Investigational
BenidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Benidipine.Approved
BepridilThe risk or severity of adverse effects can be increased when Chloroxine is combined with Bepridil.Approved, Withdrawn
BuspironeThe metabolism of Buspirone can be decreased when combined with Chloroxine.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Chloroxine.Approved, Investigational
CaiThe risk or severity of adverse effects can be increased when Chloroxine is combined with Cai.Investigational
CilnidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Cilnidipine.Approved
CinnarizineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Cinnarizine.Approved
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Chloroxine.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Clevidipine.Approved
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Chloroxine.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Chloroxine.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Chloroxine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Chloroxine is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Chloroxine.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Chloroxine.Approved
DotarizineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Efonidipine.Approved
EperisoneThe risk or severity of adverse effects can be increased when Chloroxine is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Chloroxine.Approved
FelodipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Fendiline.Withdrawn
FlunarizineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Flunarizine.Approved
FosphenytoinThe serum concentration of Chloroxine can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Chloroxine is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Chloroxine is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Lacidipine.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Lercanidipine.Approved, Investigational
LosartanThe metabolism of Losartan can be decreased when combined with Chloroxine.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Chloroxine is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Manidipine.Approved
MibefradilThe risk or severity of adverse effects can be increased when Chloroxine is combined with Mibefradil.Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Chloroxine is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Nilvadipine.Approved
NimesulideThe risk or severity of adverse effects can be increased when Chloroxine is combined with Nimesulide.Approved, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Nitrendipine.Approved
PerhexilineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Perhexiline.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Chloroxine.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Chloroxine.Approved
PimozideChloroxine may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Chloroxine is combined with Pinaverium.Approved
PregabalinThe risk or severity of adverse effects can be increased when Chloroxine is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Prenylamine.Withdrawn
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Chloroxine.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Chloroxine.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Chloroxine.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Chloroxine.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Chloroxine.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Chloroxine.Approved
RisedronateThe risk or severity of adverse effects can be increased when Chloroxine is combined with Risedronate.Approved, Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Chloroxine.Approved
SucralfateSucralfate can cause a decrease in the absorption of Chloroxine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Chloroxine.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Chloroxine.Approved, Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Chloroxine is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Chloroxine is combined with Tranilast.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Chloroxine is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Chloroxine is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Chloroxine.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (61.8 KB)
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point179.5 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.58 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyquinolines. These are compounds containing a quinoline moiety bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassHydroxyquinolines
Direct ParentHydroxyquinolines
Alternative Parents
Substituents
  • Chloroquinoline
  • 8-hydroxyquinoline
  • Hydroxyquinoline
  • 2-halophenol
  • 4-halophenol
  • 1,3-dichlorobenzene
  • Chlorobenzene
  • Benzenoid
  • Pyridine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23