Basic information
- CAS
72-80-0- Standard SMILES
Cc1ccc2c(Cl)cc(Cl)c(O)c2n1- InChIKey
GPTXWRGISTZRIO-UHFFFAOYSA-N- Molecular formula
- C10H7Cl2NO
- Average molar mass
- 228.07 g/mol
- Monoisotopic mass
- 226.9904692
Overview
Chlorquinaldol is a monohydroxyquinoline that is quinolin-8-ol which is substituted by a methyl group at position 2 and by chlorine at positions 5 and 7. An antifungal and antibacterial, it was formerly used for topical treatment of skin conditions and vaginal infections. It has a role as an antiprotozoal drug, an antibacterial drug and an antiseptic drug. It is an organochlorine compound and a monohydroxyquinoline.
Names & identifiers
- Preferred name
- Chlorquinaldol
- IUPAC
- 5,7-dichloro-2-methylquinolin-8-ol
- English name
- 5,7-Dichloro-8-hydroxyquinaldine
- Molecular formula
- C10H7Cl2NO
- Molecular weight
- 228.07
Names & synonyms
Chlorquinaldol72-80-05,7-Dichloro-8-hydroxyquinaldine5,7-dichloro-2-methylquinolin-8-olChloroquinaldolClorquinaldolSteroxin5,7-Dichloro-8-hydroxy-2-methylquinoline5,7-Dichloro-2-methyl-8-quinolinolChlorquinaldolum5,7-Dichloro-8-quinaldinolChlorchinaldol
Show more names
ChlorquinalolQuesilSiogenSiogeneSiogenoSioseptAfungilIntensol
Clorchinaldolo5,7-Dichloro-2-methyl-8-hydroxyquinolineNSC-755830DTXSID3048998D6VHC87LLSDTXCID30289242-methyl-5,7-dichloro-8-hydroxyquinolineCHEBI:74500
Database identifiers
- CAS
72-80-0- PubChem CID
- 6301
- DTXSID
DTXSID3048998- ChEMBL
CHEMBL224325- ChEBI
CHEBI:74500
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
- 14
- Formal charge
- 0
- Complexity
- 214
Experimental & physicochemical properties
Melting Point108-112
Physicochemical properties
- Melting point
- 108 · 108-112 °C (dec.)(lit.)
- Boiling point
- 350.7 · 350.7±37.0 °C(Predicted)
- Density
- 1.3126 · 1.3126 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO, Methaol (Slightly)
- form
- Solid
- pka
- 2.47 · 2.47±0.30(Predicted)
- color
- Dark Beige to Very Dark Beige
- Water Solubility
- Insoluble
- Merck
- 13 · 13,2209
- BRN
- 156683 · 156683
- InChI
- 1S/C10H7Cl2NO/c1-5-2-3-6-7(11)4-8(12)10(14)9(6)13-5/h2-4,14H,1H3
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
Warning
H302 (98.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 69 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: 8-Quinolinol, 5,7-dichloro-2-methyl-
Other Safety InformationIMAP assessments - 8-Quinolinol, 5,7-dichloro-2-methyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (98.6%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- VC5600000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 2933998090
- risk_code
- 22-36/37/38-23/24/25
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T
- safety_code
- 26-36-36/37/39-45
- Storage Class
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
P - Antiparasitic products, insecticides and repellents
R - Respiratory system
G - Genito urinary system and sex hormones
QR - Respiratory system
QG - Genito urinary system and sex hormones
PharmacodynamicsChlorquinaldol is bacteriocidal in both gram positive and gram negative bacteria. It is more effective in targeting gram positive bacteria, particularly staphylococci.
Mechanism of Action
The mechanism by which Chlorquinaldol exerts it's bacteriocidal effect is unknown. 8-hydroxyquinolines are known to be bidentate chelators of several metal ions which act as critical enzyme cofactors. However, the addition of exogenous metal ions does not appear to alter the minimum inhibitory concentration for mycobacterium tuberculosis suggesting that the primary mechanism does not rely on chelation.
Metabolism/Metabolites98% of drug is converted to the sulfate form and renally excreted.
FDA Pharmacological Classification
D6VHC87LLS
CHLORQUINALDOL
Established Pharmacologic Class [EPC] - Standardized Chemical Allergen
Physiologic Effects [PE] - Increased Histamine Release
Physiologic Effects [PE] - Cell-mediated Immunity
Chemical Structure [CS] - Allergens
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Absorption, Distribution and Excretion
There is a high degree of variability in the extent of absorption of topically applied chorquinaldol preparations. It is reported to be between 4.2 and 23.5% of the applied dose. This is quite low compared to orally administered preparations which displayed 67.6% absorption in the same study.
Related reactions
13 records
Compound notes
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