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.

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
AgmatineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Chloroxine can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Chloroxine.Approved, Investigational
AmrinoneThe therapeutic efficacy of Chloroxine can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Aranidipine.Approved, Investigational
AzelnidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Chloroxine can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Barnidipine.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Chloroxine.Investigational
BencyclaneThe therapeutic efficacy of Chloroxine can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Chloroxine can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Chloroxine can be increased when used in combination with Bioallethrin.Approved, Experimental
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 therapeutic efficacy of Chloroxine can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Chloroxine.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Chloroxine can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Chloroxine.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Chloroxine can be increased when used in combination 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 therapeutic efficacy of Chloroxine can be increased when used in combination with Diltiazem.Approved, Investigational
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, Investigational
DotarizineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Chloroxine can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Chloroxine can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Chloroxine.Approved
FelodipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Chloroxine can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Chloroxine can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Chloroxine can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Chloroxine can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Chloroxine can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Chloroxine can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Chloroxine can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Chloroxine.Approved
Magnesium sulfateThe therapeutic efficacy of Chloroxine can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Chloroxine can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Chloroxine can be increased when used in combination with Methsuximide.Approved
MibefradilThe therapeutic efficacy of Chloroxine can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Chloroxine can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Chloroxine can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Chloroxine can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Chloroxine can be increased when used in combination with Otilonium.Experimental, 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 therapeutic efficacy of Chloroxine can be increased when used in combination with Pinaverium.Approved
PrenylamineThe therapeutic efficacy of Chloroxine can be increased when used in combination 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, Investigational
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, Investigational
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, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Chloroxine.Approved, Investigational
SeletracetamThe therapeutic efficacy of Chloroxine can be increased when used in combination with Seletracetam.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 therapeutic efficacy of Chloroxine can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Chloroxine can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Chloroxine can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Chloroxine can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Chloroxine can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Chloroxine can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Chloroxine can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Chloroxine can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Chloroxine.Approved
ZonisamideThe therapeutic efficacy of Chloroxine can be increased when used in combination with Zonisamide.Approved, Investigational
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
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 June 02, 2018 06:47