Basic information
- CAS
773-76-2- Standard SMILES
Oc1c(Cl)cc(Cl)c2cccnc12- InChIKey
WDFKMLRRRCGAKS-UHFFFAOYSA-N- Molecular formula
- C9H5Cl2NO
- Average molar mass
- 214.04 g/mol
- Monoisotopic mass
- 212.9748192
Overview
Chloroxine is a monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 have been substituted by chlorine. A synthetic antibacterial prepared by chlorination of quinolin-8-ol, it is used for the treatment of dandruff and seborrhoeic dermatitis of the scalp. It has a role as an antibacterial agent, an antiseborrheic and an antifungal drug. It is an organochlorine compound and a monohydroxyquinoline. It is functionally related to a quinolin-8-ol.
Names & identifiers
- Preferred name
- Chloroxine
- IUPAC
- 5,7-dichloroquinolin-8-ol
- English name
- 5,7-Dichloro-8-hydroxyquinoline
- Molecular formula
- C9H5Cl2NO
- Molecular weight
- 214.05
Names & synonyms
chloroxine773-76-25,7-Dichloroquinolin-8-ol5,7-Dichloro-8-hydroxyquinoline5,7-Dichloro-8-quinolinolChlorquinolCapitrolQuixalinDichlorohydroxyquinoline5,7-Dichlorooxine5,7-Dichloroxine8-QUINOLINOL, 5,7-DICHLORO-
Show more names
CHQQuesylClofuzidEndiaronChlofucidDichloroxinChhoroox-ine
5,7-Dichloro-8-oxyquinoline5,7-Dichlor-8-hydroxychinolinDTXSID5022801NSC-39042I8BD50I8BCHEBI:59477NSC3904DTXCID202801
Database identifiers
- CAS
773-76-2- PubChem CID
- 2722
- DTXSID
DTXSID5022801- ChEMBL
CHEMBL1200596- ChEBI
CHEBI:59477- UNII
- 2I8BD50I8B
- EC Number
- 212-258-3
- Nikkaji
- J7.088B
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 33.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 190
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
LogP3
Solubility1.38e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point179.5 °C
Physical DescriptionSolid
Collision Cross Section
132.71 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
134.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (93.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 77 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (93.5%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- VC5350000
- hs_code
- 29334900
- risk_code
- 22-37/38-41-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-36-37/39-25-22
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H318-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2STOT SE 3
Chemistry & industry
Pharmacology
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 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.
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Substances that inhibit the growth or reproduction of BACTERIA.
Cellular LocationsMembrane
Uses & manufacturing
General Manufacturing Information8-Quinolinol, 5,7-dichloro-: ACTIVE
Applications
UsesH1 antihistamine
UsesAnalytical reagent.
UsesChloroxine, is an impurity of Cioquinol, which is an antifungal and antiprotozoal drug.
Upstream & downstream products
Upstream raw materials
Related reactions
2 records
Compound notes
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