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
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.

Structured Indications
Not Available
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
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, Investigational
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
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Chloroxine.Investigational
BencyclaneThe risk or severity of adverse effects can be increased when Chloroxine is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Benidipine.Approved, Investigational
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
CarboxyamidotriazoleThe risk or severity of adverse effects can be increased when Chloroxine is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Caroverine.Experimental
CilnidipineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Cilnidipine.Approved, Investigational
CinnarizineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Cinnarizine.Approved, Investigational
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
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 serum concentration of Dofetilide can be increased when it is 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, Investigational
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, Investigational
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
LidoflazineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Lidoflazine.Experimental
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, Investigational
MibefradilThe risk or severity of adverse effects can be increased when Chloroxine is combined with Mibefradil.Investigational, 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, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Chloroxine is combined with Nimesulide.Approved, Investigational, 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, Investigational
OtiloniumThe risk or severity of adverse effects can be increased when Chloroxine is combined with Otilonium.Experimental, Investigational
PerhexilineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Perhexiline.Approved, Investigational
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
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 absorption of Progesterone can be decreased when combined with Chloroxine.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Chloroxine.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is 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
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Chloroxine.Approved, Investigational
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
TerodilineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Tetrahydropalmatine.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 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
HMDB15373
PubChem Compound
2722
PubChem Substance
46508620
ChemSpider
2621
BindingDB
32187
ChEBI
59477
ChEMBL
CHEMBL1200596
PharmGKB
PA164754879
Drugs.com
Drugs.com Drug Page
MSDS
Download (61.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
Not Available
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 November 09, 2017 02:58