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
- 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.
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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
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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
- 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