Chloroxine
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Overview
- Description
- A medication used to treat dandruff and inflammation of the scalp.
- Description
- A medication used to treat dandruff and inflammation of the scalp.
- DrugBank ID
- DB01243
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
- Kappa-type opioid receptorInhibitor
- Kappa-type opioid receptor
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Dermatosis Combination Product in combination with: Betamethasone (DB00443) •••••••••••• •••••• •••••••• Treatment of Dermatosis •••••••••••• ••••• Treatment of Dermatosis •••••••••••• ••••• Used in combination to prevent Fungal skin infection Combination Product in combination with: Betamethasone (DB00443) •••••••••••• •••••• •••••••• Used in combination to treat Intertrigo Combination Product in combination with: Betamethasone (DB00443) •••••••••••• •••••• •••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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.
Target Actions Organism AKappa-type opioid receptor inhibitorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareEstetrol The therapeutic efficacy of Estetrol can be decreased when used in combination with Chloroxine. Fecal microbiota The therapeutic efficacy of Fecal microbiota can be decreased when used in combination with Chloroxine. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Endiaron
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Capitrol Shampoo 20 mg/1g Topical Bristol Myers Squibb Pharma Company 2009-06-01 2012-10-15 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BEBEN CLOROSSINA Chloroxine (0.5 %) + Betamethasone benzoate (0.025 %) Cream Topical Teofarma S.R.L. 2014-07-08 Not applicable Italy BEBEN CLOROSSINA Chloroxine (0.5 %) + Betamethasone benzoate (0.1 %) Ointment Topical Teofarma S.R.L. 2014-07-08 2022-05-20 Italy BEBEN CLOROSSINA Chloroxine (0.5 %) + Betamethasone benzoate (0.1 %) Ointment Topical Teofarma S.R.L. 2014-07-08 2021-07-21 Italy BEBEN CLOROSSINA Chloroxine (0.5 %) + Betamethasone benzoate (0.1 %) Cream Topical Teofarma S.R.L. 2014-07-08 Not applicable Italy BEBEN CLOROSSINA Chloroxine (0.5 %) + Betamethasone benzoate (0.1 %) Cream Topical Teofarma S.R.L. 2014-07-08 2022-05-20 Italy
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
- 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]
- 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]
- External Links
- Human Metabolome Database
- HMDB0015373
- KEGG Drug
- D03472
- PubChem Compound
- 2722
- PubChem Substance
- 46508620
- ChemSpider
- 2621
- BindingDB
- 32147
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Contract Pharm
- Dosage Forms
Form Route Strength Cream Topical Emulsion Topical Lotion Topical Ointment Topical Shampoo Topical 20 mg/1g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 179.5 °C PhysProp logP 3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.138 mg/mL ALOGPS logP 3.44 ALOGPS logP 3.04 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 6.95 Chemaxon pKa (Strongest Basic) 3.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 33.12 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 51.57 m3·mol-1 Chemaxon Polarizability 19.32 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.997 Blood Brain Barrier + 0.9817 Caco-2 permeable + 0.7378 P-glycoprotein substrate Non-substrate 0.7232 P-glycoprotein inhibitor I Non-inhibitor 0.9655 P-glycoprotein inhibitor II Non-inhibitor 0.9471 Renal organic cation transporter Non-inhibitor 0.8087 CYP450 2C9 substrate Non-substrate 0.759 CYP450 2D6 substrate Non-substrate 0.7206 CYP450 3A4 substrate Non-substrate 0.592 CYP450 1A2 substrate Inhibitor 0.8973 CYP450 2C9 inhibitor Non-inhibitor 0.8853 CYP450 2D6 inhibitor Non-inhibitor 0.9131 CYP450 2C19 inhibitor Non-inhibitor 0.7778 CYP450 3A4 inhibitor Non-inhibitor 0.9473 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6649 Ames test Non AMES toxic 0.9244 Carcinogenicity Non-carcinogens 0.9514 Biodegradation Not ready biodegradable 0.9771 Rat acute toxicity 2.2486 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8542 hERG inhibition (predictor II) Non-inhibitor 0.8636
Spectra
- Mass Spec (NIST)
- Download (8.58 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 130.4051429 predictedDarkChem Lite v0.1.0 [M-H]- 135.55235 predictedDeepCCS 1.0 (2019) [M+H]+ 131.0069429 predictedDarkChem Lite v0.1.0 [M+H]+ 138.0742 predictedDeepCCS 1.0 (2019) [M+Na]+ 130.4542429 predictedDarkChem Lite v0.1.0 [M+Na]+ 146.42073 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- G-protein coupled opioid receptor that functions as a receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as a receptor for various synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain. Plays a role in mediating reduced physical activity upon treatment with synthetic opioids. Plays a role in the regulation of salivation in response to synthetic opioids. May play a role in arousal and regulation of autonomic and neuroendocrine functions
- Specific Function
- dynorphin receptor activity
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:24