Oxyquinoline

Identification

Name
Oxyquinoline
Accession Number
DB11145
Type
Small Molecule
Groups
Approved, Vet approved
Description

Oxyquinoline is a heterocyclic phenol and derivative of quinoline with antiseptic, disinfectant, and pesticide properties. It is used as a stabilizer for hydrogen peroxide, where it is sometimes added in cosmetic products.

Structure
Thumb
Synonyms
  • 8-Hydroxyquinoline
  • hydroxybenzopyridine
  • Hydroxyquinoline
  • oxine
  • Phenopyridine
External IDs
J2.960B
Product Ingredients
IngredientUNIICASInChI Key
8-Hydroxyquinoline citrateK522O2O40B134-30-5GTOQWWQKBBZILU-UHFFFAOYSA-N
8-Hydroxyquinoline hydrochlorideNot Available16862-11-6GXBJNMSTHMBPPE-UHFFFAOYSA-N
8-Hydroxyquinoline salicylate98Z1AMM4PS2439-07-8GOEKBPHGLUYFOX-UHFFFAOYSA-N
8-Hydroxyquinoline sulfateNot Available1130-05-8MRUMAIRJPMUAPZ-UHFFFAOYSA-N
Oxyquinoline sulfate61VUG75Y3P134-31-6YYVFXSYQSOZCOQ-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ArkodyneOxyquinoline sulfate (3 mg) + Benzalkonium chloride (1.5 mg) + Benzocaine (4 mg)LozengeOralLaboratoire Romilo1980-12-311999-08-18Canada
New Skin Clear Liquid BandageOxyquinoline (1 %) + Clove oil (.8 %)LiquidTopicalMedtech Laboratories, Inc.1969-12-311998-07-08Canada
New Skin Clear Spray BandageOxyquinoline (1 %) + Clove oil (.8 %)AerosolTopicalMedtech Laboratories, Inc.1969-12-311998-07-08Canada
Racestyptine CordOxyquinoline sulfate (.24 mg) + Aluminum chloride (60 mg) + Lidocaine (35 mg)PackingDentalSeptodont1981-12-312000-08-03Canada
Racestyptine SolOxyquinoline sulfate (100 mg) + Aluminum chloride (25 g)LiquidDentalSeptodont1977-12-31Not applicableCanada
Sulpak IIOxyquinoline sulfate (.1 %) + Aluminum chloride (25 %)LiquidDentalNorth Pacific Dental Inc.1983-12-311997-12-22Canada
Trimo San Deodorant Vaginal JellyOxyquinoline sulfate (0.025 %) + Boric acid (1.0 %) + Sodium borate (0.7 %)JellyVaginalMilex Products Ltd.1979-12-312005-07-25Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Fem pHOxyquinoline sulfate (0.00025 g/1g) + Acetic acid (0.009 g/1g)JellyVaginalPharmics, Inc.1999-07-15Not applicableUs
RelegardOxyquinoline (0.025 mg/1mL) + Acetic acid (0.9 mg/1mL)GelTopicalBlansett Pharmacal Co2017-03-20Not applicableUs
Trimo SanOxyquinoline sulfate (0.25 mg/1g) + Sodium lauryl sulfate (0.1 mg/1g)JellyVaginalCooperSurgical, Inc.1977-04-01Not applicableUs
Categories
UNII
5UTX5635HP
CAS number
148-24-3
Weight
Average: 145.158
Monoisotopic: 145.052763851
Chemical Formula
C9H7NO
InChI Key
MCJGNVYPOGVAJF-UHFFFAOYSA-N
InChI
InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
IUPAC Name
quinolin-8-ol
SMILES
OC1=CC=CC2=C1N=CC=C2

Pharmacology

Indication

Oxyquinoline is used as a biocidal component of several over the counter products. These products are marketed for the purposes of inhibiting abnormal biological growth in the vagina and restoring natural pH.

Pharmacodynamics

Oxyquinoline acts as a biocide to eliminate bacteria and fungi [1].

Mechanism of action

The mechanism by which oxyquinoline exerts its biocidal effect is unknown.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

In the urine, 60% of the dose is excreted as glucuronide conjugates and 23% of the dose as sulfate conjugates [1]. In the bile, 9% of the total dose is found as glucuronide conjugates.

Route of elimination

Oxyquinoline is excreted in both the primarily in the urine with some in the bile [1].

Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Aspergillis, Candida and other fungi
  • Trichomonas vaginalis, Giardia duodenalis, and Entamoeba histolytica
  • Pseudomonas aeruginosa
  • Escherichia coli
  • Staphylococcus aureus
  • Klebsiella pneumoniae
  • Pseudomonas fluorescens
  • Pseudomonas cepacia
  • Penicillium notatum
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetaminophenAcetaminophen may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
Adefovir DipivoxilAdefovir Dipivoxil may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AlmotriptanAlmotriptan may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AlprazolamAlprazolam may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AmantadineAmantadine may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AmilorideAmiloride may increase the excretion rate of Oxyquinoline which could result in a lower serum level and potentially a reduction in efficacy.
AmitriptylineOxyquinoline may decrease the excretion rate of Amitriptyline which could result in a higher serum level.
AmlodipineAmlodipine may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
Food Interactions
Not Available

References

Synthesis Reference

International Agency for Research on Cancer (IARC). 1977. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, vol. 13, pages 101-112 . Lyon, IARC.

General References
  1. Andersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9. [PubMed:16835127]
  2. IARC Monographs Volume 13 [Link]
External Links
KEGG Compound
C19434
PubChem Compound
1923
PubChem Substance
347827918
ChemSpider
1847
BindingDB
32203
ChEBI
48981
ChEMBL
CHEMBL310555
HET
HQY
Wikipedia
8-Hydroxyquinoline
ATC Codes
R02AA14 — OxyquinolineD08AH03 — OxyquinolineG01AC30 — OxyquinolineA01AB07 — Oxyquinoline
PDB Entries
3kcy / 3vh9 / 4jfg

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LozengeOral
LiquidTopical
AerosolTopical
PackingDental
GelTopical
LiquidDental
JellyVaginal
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)76Andersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9.
boiling point (°C)267Andersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9.
water solubilityInsolubleAndersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9.
pKa5.017Andersen A: Final amended report on the safety assessment of oxyquinoline and oxyquinoline sulfate as used in cosmetics. Int J Toxicol. 2006;25 Suppl 1:1-9.
Predicted Properties
PropertyValueSource
Water Solubility4.18 mg/mLALOGPS
logP1.91ALOGPS
logP1.83ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.36ChemAxon
pKa (Strongest Basic)4.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.96 m3·mol-1ChemAxon
Polarizability14.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-00kb-4900000000-dbee61b764231929582e
GC-MS Spectrum - EI-BGC-MSsplash10-00kb-8900000000-9f44d33e560065cf0670
Mass Spectrum (Electron Ionization)MSsplash10-00kb-6900000000-884423812367e06a25fa
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-ITFT , positiveLC-MS/MSsplash10-014i-0900000000-98366904cdd9ed4a8caa
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as 8-hydroxyquinolines. These are compounds containing a quinoline moiety, which carries a hydroxy group at the 8-position. Quinoline consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
8-hydroxyquinolines
Direct Parent
8-hydroxyquinolines
Alternative Parents
1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Pyridines and derivatives / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
8-hydroxyquinoline / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Benzenoid / Pyridine / Heteroaromatic compound / Azacycle / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monohydroxyquinoline (CHEBI:48981) / a small molecule (8-HYDROXYQUINOLINE)

Drug created on December 03, 2015 09:51 / Updated on October 01, 2018 16:55