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
Structure for Oxyquinoline (DB11145)
- 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.
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 for therapy Gingival bleeding Combination Product in combination with: Aluminum chloride (DB11081) •••••••••••• •••••••• - Associated Therapies
- 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
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.
Hover over products below to view reaction partners
- 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
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
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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Oxyquinoline which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Oxyquinoline which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Oxyquinoline which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Oxyquinoline which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Oxyquinoline which could result in a lower serum level and potentially a reduction in efficacy. - 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.- Product Ingredients
Ingredient UNII CAS InChI Key 8-Hydroxyquinoline citrate K522O2O40B 134-30-5 GTOQWWQKBBZILU-UHFFFAOYSA-N 8-Hydroxyquinoline hydrochloride Not Available 16862-11-6 GXBJNMSTHMBPPE-UHFFFAOYSA-N 8-Hydroxyquinoline salicylate 98Z1AMM4PS 2439-07-8 GOEKBPHGLUYFOX-UHFFFAOYSA-N 8-Hydroxyquinoline sulfate Not Available 1130-05-8 MRUMAIRJPMUAPZ-UHFFFAOYSA-N Oxyquinoline sulfate 61VUG75Y3P 134-31-6 YYVFXSYQSOZCOQ-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Arkodyne Oxyquinoline sulfate (3 mg / loz) + Benzalkonium chloride (1.5 mg / loz) + Benzocaine (4 mg / loz) Lozenge Oral Laboratoire Romilo 1980-12-31 1999-08-18 Canada 
New Skin Clear Liquid Bandage Oxyquinoline (1 %) + Clove oil (.8 %) Liquid Topical Medtech Laboratories, Inc. 1969-12-31 1998-07-08 Canada New Skin Clear Spray Bandage Oxyquinoline (1 %) + Clove oil (.8 %) Aerosol Topical Medtech Laboratories, Inc. 1969-12-31 1998-07-08 Canada Racestyptine Cord Oxyquinoline sulfate (.24 mg / 100 cm) + Aluminum chloride (60 mg / 100 cm) + Lidocaine (35 mg / 100 cm) Packing Dental Septodont 1981-12-31 2000-08-03 Canada Racestyptine Sol Oxyquinoline sulfate (100 mg / 100 mL) + Aluminum chloride (25 g / 100 mL) Liquid Dental Septodont 1977-12-31 2017-07-07 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Fem pH Oxyquinoline sulfate (0.00025 g/1g) + Acetic acid (0.009 g/1g) Jelly Vaginal Pharmics, Inc. 1999-07-15 Not applicable US 
Relegard Oxyquinoline (0.025 mg/1mL) + Acetic acid (0.9 mg/1mL) Gel Topical Blansett Pharmacal Co 2017-03-20 Not applicable US Trimo San Oxyquinoline sulfate (0.25 mg/1g) + Sodium lauryl sulfate (0.1 mg/1g) Jelly Vaginal CooperSurgical, Inc. 1977-04-01 Not applicable US Trimo-San Oxyquinoline sulfate (0.25 mg/1g) + Sodium lauryl sulfate (0.1 mg/1g) Jelly Vaginal Denison Pharmaceuticals, Llc 2019-09-16 Not applicable US
Categories
- ATC Codes
- R02AA14 — OxyquinolineA01AB07 — Oxyquinoline
- A01AB — Antiinfectives and antiseptics for local oral treatment
- A01A — STOMATOLOGICAL PREPARATIONS
- A01 — STOMATOLOGICAL PREPARATIONS
- A — ALIMENTARY TRACT AND METABOLISM
- D08AH — Quinoline derivatives
- D08A — ANTISEPTICS AND DISINFECTANTS
- D08 — ANTISEPTICS AND DISINFECTANTS
- D — DERMATOLOGICALS
- Drug Categories
- Alimentary Tract and Metabolism
- Anti-Infective Agents, Local
- Antiinfectives and Antiseptics for Local Oral Treatment
- Antiseptics and Disinfectants
- Dermatologicals
- Drugs that are Mainly Renally Excreted
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Heterocyclic Compounds, Fused-Ring
- Hydroxyquinolines
- Quinoline Derivatives
- Quinolines
- Stomatological Preparations
- Throat Preparations
- 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
- External Links
- KEGG Compound
- C19434
- PubChem Compound
- 1923
- PubChem Substance
- 347827918
- ChemSpider
- 1847
- BindingDB
- 32203
- 110
- ChEBI
- 48981
- ChEMBL
- CHEMBL310555
- ZINC
- ZINC000000008492
- PDBe Ligand
- HQY
- Wikipedia
- 8-Hydroxyquinoline
- PDB Entries
- 3kcy / 3vh9 / 4jfg
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Terminated Treatment Bacterial Vaginosis (BV) / Vaginal Discharge / Vaginosis 1 2, 3 Completed Prevention Bacterial Vaginosis (BV) 1 1 Recruiting Diagnostic Chronic Fatigue Syndrome/ Myalgic Encephalitis (CFS/ME) / Fibromyalgia / Healthy Volunteers (HV) / Multiple Sclerosis 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Lozenge Oral Injection, solution Intravenous Liquid Topical Aerosol Topical Packing Dental Gel Topical Liquid Dental Jelly Vaginal Cream Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 76 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. boiling point (°C) 267 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. water solubility Insoluble 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. pKa 5.017 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. - Predicted Properties
Property Value Source Water Solubility 4.18 mg/mL ALOGPS logP 1.91 ALOGPS logP 1.83 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 9.36 Chemaxon pKa (Strongest Basic) 4.83 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 33.12 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 41.96 m3·mol-1 Chemaxon Polarizability 14.87 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 124.69508 predictedDeepCCS 1.0 (2019) [M+H]+ 127.6107 predictedDeepCCS 1.0 (2019) [M+Na]+ 136.63724 predictedDeepCCS 1.0 (2019)
Drug created at December 03, 2015 16:51 / Updated at February 21, 2021 18:52