Chloroxine

Identification

Summary

Chloroxine is an antibacterial agent used for the treatment of dandruff and mild to moderately severe seborrheic dermatitis of the scalp.

Generic Name
Chloroxine
DrugBank Accession Number
DB01243
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 214.048
Monoisotopic: 212.974819201
Chemical Formula
C9H5Cl2NO
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
  • Chloroxine
  • Chlorquinol
  • CHQ
External IDs
  • SQ 16401

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatDermatosisCombination Product in combination with: Betamethasone (DB00443)•••••••••••••••••• ••••••••
Treatment ofDermatosis•••••••••••••••••
Treatment ofDermatosis•••••••••••••••••
Used in combination to preventFungal skin infectionCombination Product in combination with: Betamethasone (DB00443)•••••••••••••••••• ••••••••
Used in combination to treatIntertrigoCombination Product in combination with: Betamethasone (DB00443)•••••••••••••••••• ••••••••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

The toxicological properties of this material have not been investigated.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
EstetrolThe therapeutic efficacy of Estetrol can be decreased when used in combination with Chloroxine.
Fecal microbiotaThe therapeutic efficacy of Fecal microbiota can be decreased when used in combination with Chloroxine.
Food Interactions
No interactions found.

Products

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International/Other Brands
Endiaron
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CapitrolShampoo20 mg/1gTopicalBristol Myers Squibb Pharma Company2009-06-012012-10-15US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BEBEN CLOROSSINAChloroxine (0.5 %) + Betamethasone benzoate (0.1 %)OintmentTopicalTeofarma S.R.L.2014-07-082022-06-24Italy flag
BEBEN CLOROSSINAChloroxine (0.5 %) + Betamethasone (0.1 %)LotionTopicalTeofarma S.R.L.2014-07-082022-06-24Italy flag
BEBEN CLOROSSINAChloroxine (0.5 %) + Betamethasone benzoate (0.025 %)CreamTopicalTeofarma S.R.L.2014-07-08Not applicableItaly flag
BEBEN CLOROSSINAChloroxine (0.5 %) + Betamethasone benzoate (0.1 %)OintmentTopicalTeofarma S.R.L.2014-07-082022-05-20Italy flag
BEBEN CLOROSSINAChloroxine (0.5 %) + Betamethasone benzoate (0.1 %)OintmentTopicalTeofarma S.R.L.2014-07-082021-07-21Italy flag

Categories

Drug Categories
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 / Pyridines and derivatives / 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 / Organic nitrogen compound
show 7 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, monohydroxyquinoline (CHEBI:59477)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
2I8BD50I8B
CAS number
773-76-2
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

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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0015373
KEGG Drug
D03472
PubChem Compound
2722
PubChem Substance
46508620
ChemSpider
2621
BindingDB
32147
RxNav
20875
ChEBI
59477
ChEMBL
CHEMBL1200596
ZINC
ZINC000000001131
PharmGKB
PA164754879
Drugs.com
Drugs.com Drug Page
Wikipedia
Chloroxine
MSDS
Download (61.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Contract Pharm
Dosage Forms
FormRouteStrength
CreamTopical
EmulsionTopical
LotionTopical
OintmentTopical
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-MSsplash10-03di-1980000000-94c636ec42678fc3c467
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03xr-2790000000-123a4bb6fd1928cb1de5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xr-0390000000-37c6d6830bd09ef8b180
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xr-2790000000-123a4bb6fd1928cb1de5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-a0de523a96ccfbdfee5f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-aabaafc0b59fbf20f6fb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-ce0339886dc6f806ef0a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-70fee615f541046c16f6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0910000000-ee842cbd85a6fb831675
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1920000000-08b452d21bf4f0bb3a3b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-130.4051429
predicted
DarkChem Lite v0.1.0
[M-H]-135.55235
predicted
DeepCCS 1.0 (2019)
[M+H]+131.0069429
predicted
DarkChem Lite v0.1.0
[M+H]+138.0742
predicted
DeepCCS 1.0 (2019)
[M+Na]+130.4542429
predicted
DarkChem Lite v0.1.0
[M+Na]+146.42073
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at June 16, 2021 12:30