Oxyquinoline

Identification

Summary

Oxyquinoline is a medication used in combination with other medications to restore vaginal pH.

Brand Names
Fem Ph, Relagard
Generic Name
Oxyquinoline
DrugBank Accession Number
DB11145
Background

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.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 145.158
Monoisotopic: 145.052763851
Chemical Formula
C9H7NO
Synonyms
  • 8-Hydroxyquinoline
  • hydroxybenzopyridine
  • Hydroxyquinoline
  • oxine
  • Oxyquinoline
  • Phenopyridine
External IDs
  • J2.960B

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.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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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.

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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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

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
AbacavirAbacavir may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Oxyquinoline which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Oxyquinoline which could result in a higher serum level.
AcrivastineAcrivastine 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.
Interactions
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Food Interactions
No interactions found.

Products

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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 EndRegionImage
ArkodyneOxyquinoline sulfate (3 mg / loz) + Benzalkonium chloride (1.5 mg / loz) + Benzocaine (4 mg / loz)LozengeOralLaboratoire Romilo1980-12-311999-08-18Canada flag
New Skin Clear Liquid BandageOxyquinoline (1 %) + Clove oil (.8 %)LiquidTopicalMedtech Laboratories, Inc.1969-12-311998-07-08Canada flag
New Skin Clear Spray BandageOxyquinoline (1 %) + Clove oil (.8 %)AerosolTopicalMedtech Laboratories, Inc.1969-12-311998-07-08Canada flag
Racestyptine CordOxyquinoline sulfate (.24 mg / 100 cm) + Aluminum chloride (60 mg / 100 cm) + Lidocaine (35 mg / 100 cm)PackingDentalSeptodont1981-12-312000-08-03Canada flag
Racestyptine SolOxyquinoline sulfate (100 mg / 100 mL) + Aluminum chloride (25 g / 100 mL)LiquidDentalSeptodont1977-12-312017-07-07Canada flag
Sulpak IIOxyquinoline sulfate (.1 %) + Aluminum chloride (25 %)LiquidDentalNorth Pacific Dental Inc.1983-12-311997-12-22Canada flag
Trimo San Deodorant Vaginal JellyOxyquinoline sulfate (0.025 %) + Boric acid (1.0 %) + Sodium borate (0.7 %)JellyVaginalMilex Products Ltd.1979-12-312005-07-25Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Fem pHOxyquinoline sulfate (0.00025 g/1g) + Acetic acid (0.009 g/1g)JellyVaginalPharmics, Inc.1999-07-15Not applicableUS flag
RelegardOxyquinoline (0.025 mg/1mL) + Acetic acid (0.9 mg/1mL)GelTopicalBlansett Pharmacal Co2017-03-20Not applicableUS flag
Trimo SanOxyquinoline sulfate (0.25 mg/1g) + Sodium lauryl sulfate (0.1 mg/1g)JellyVaginalCooperSurgical, Inc.1977-04-01Not applicableUS flag
Trimo-SanOxyquinoline sulfate (0.25 mg/1g) + Sodium lauryl sulfate (0.1 mg/1g)JellyVaginalDenison Pharmaceuticals, Llc2019-09-16Not applicableUS flag

Categories

ATC Codes
R02AA14 — OxyquinolineA01AB07 — OxyquinolineD08AH03 — OxyquinolineG01AC30 — Oxyquinoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 8-hydroxyquinoline / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monohydroxyquinoline (CHEBI:48981) / a small molecule (8-HYDROXYQUINOLINE)
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

Chemical Identifiers

UNII
5UTX5635HP
CAS number
148-24-3
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

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. [Article]
  2. IARC Monographs Volume 13 [Link]
KEGG Compound
C19434
PubChem Compound
1923
PubChem Substance
347827918
ChemSpider
1847
BindingDB
32203
RxNav
110
ChEBI
48981
ChEMBL
CHEMBL310555
ZINC
ZINC000000008492
PDBe Ligand
HQY
Wikipedia
8-Hydroxyquinoline
PDB Entries
3kcy / 3vh9 / 4jfg

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentBacterial Vaginosis (BV) / Vaginal Discharge / Vaginosis1
2, 3CompletedPreventionBacterial Vaginosis (BV)1
1Not Yet RecruitingDiagnosticFibromyalgia (FM) / Healthy Subjects (HS) / Multiple Sclerosis / Myalgic Encephalomyelitis (ME)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LozengeOral
Injection, solutionIntravenous
LiquidTopical
AerosolTopical
PackingDental
GelTopical
LiquidDental
JellyVaginal
CreamTopical
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

Drug created on December 03, 2015 16:51 / Updated on February 21, 2021 18:52