Identification
- Generic Name
- Flumequine
- DrugBank Accession Number
- DB08972
- Background
Flumequine is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class used to treat bacterial infections.
- Type
- Small Molecule
- Groups
- Withdrawn
- Structure
Structure for Flumequine (DB08972)
- Weight
- Average: 261.2484
Monoisotopic: 261.08012146 - Chemical Formula
- C14H12FNO3
- Synonyms
- Flumequine
Pharmacology
- Indication
Not Available
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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
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- 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 softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Flumequine. Aceclofenac Aceclofenac may increase the neuroexcitatory activities of Flumequine. Acemetacin Acemetacin may increase the neuroexcitatory activities of Flumequine. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Flumequine. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Flumequine. - Food Interactions
- Not Available
Products
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Categories
- ATC Codes
- J01MB07 — Flumequine
- Drug Categories
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Antineoplastic Agents
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Enzyme Inhibitors
- Fluoroquinolones
- Heterocyclic Compounds, Fused-Ring
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Quinolines
- Quinolones
- Topoisomerase II Inhibitors
- Topoisomerase Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Quinolines and derivatives
- Sub Class
- Quinoline carboxylic acids
- Direct Parent
- Quinoline carboxylic acids
- Alternative Parents
- Fluoroquinolones / Haloquinolines / Hydroquinolones / Hydroquinolines / Pyridinecarboxylic acids / Aryl fluorides / Benzenoids / Heteroaromatic compounds / Vinylogous amides / Monocarboxylic acids and derivatives show 8 more
- Substituents
- Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Dihydroquinoline / Dihydroquinolone / Fluoroquinolone show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, quinolone antibiotic, 3-oxo monocarboxylic acid, pyridoquinoline (CHEBI:85269)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- UVG8VSP2SJ
- CAS number
- 42835-25-6
- InChI Key
- DPSPPJIUMHPXMA-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19)
- IUPAC Name
- 7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.0^{5,13}]trideca-2,5(13),6,8-tetraene-3-carboxylic acid
- SMILES
- CC1CCC2=CC(F)=CC3=C2N1C=C(C(O)=O)C3=O
References
- Synthesis Reference
U.S. Patent 3,896,131.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0041895
- PubChem Compound
- 3374
- PubChem Substance
- 310264935
- ChemSpider
- 3257
- 25112
- ChEBI
- 85269
- ChEMBL
- CHEMBL370252
- Wikipedia
- Flumequine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.24 mg/mL ALOGPS logP 1.62 ALOGPS logP 2.42 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 5.81 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 57.61 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 67.87 m3·mol-1 Chemaxon Polarizability 25.25 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No 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]- 160.9528542 predictedDarkChem Lite v0.1.0 [M-H]- 158.86613 predictedDeepCCS 1.0 (2019) [M+H]+ 161.4532542 predictedDarkChem Lite v0.1.0 [M+H]+ 161.22414 predictedDeepCCS 1.0 (2019) [M+Na]+ 161.0011542 predictedDarkChem Lite v0.1.0 [M+Na]+ 167.31728 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- This enzyme action is based on the drug being a member of the fluoroquinolone group of drugs. This group is known to inhibit CYP1A2.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Gunes A, Dahl ML: Variation in CYP1A2 activity and its clinical implications: influence of environmental factors and genetic polymorphisms. Pharmacogenomics. 2008 May;9(5):625-37. doi: 10.2217/14622416.9.5.625. [Article]
- Liu L, Miao MX, Zhong ZY, Xu P, Chen Y, Liu XD: Chronic administration of caderofloxacin, a new fluoroquinolone, increases hepatic CYP2E1 expression and activity in rats. Acta Pharmacol Sin. 2016 Apr;37(4):561-70. doi: 10.1038/aps.2015.160. Epub 2016 Feb 1. [Article]
- Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes [File]
- FDA label, ciprofloxacin [File]
Drug created at June 09, 2014 16:39 / Updated at February 21, 2021 18:52