Flumequine

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Withdrawn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
Thumb
Weight
Average: 261.2484
Monoisotopic: 261.08012146
Chemical Formula
C14H12FNO3
Synonyms
  • Flumequine

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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
Medicalerrors
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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
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Flumequine.
AcebutololThe risk or severity of QTc prolongation can be increased when Flumequine is combined with Acebutolol.
AceclofenacAceclofenac may increase the neuroexcitatory activities of Flumequine.
AcemetacinAcemetacin may increase the neuroexcitatory activities of Flumequine.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Flumequine.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Flumequine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Flumequine.
Acetylsalicylic acidAcetylsalicylic acid may increase the neuroexcitatory activities of Flumequine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Flumequine is combined with Acrivastine.
AcyclovirThe metabolism of Acyclovir can be decreased when combined with Flumequine.
Interactions
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Food Interactions
Not Available

Products

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Categories

ATC Codes
J01MB07 — Flumequine
Drug Categories
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[7.3.1.0⁵,¹³]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
Human Metabolome Database
HMDB0041895
PubChem Compound
3374
PubChem Substance
310264935
ChemSpider
3257
RxNav
25112
ChEBI
85269
ChEMBL
CHEMBL370252
Wikipedia
Flumequine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.24 mg/mLALOGPS
logP1.62ALOGPS
logP2.42ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.87 m3·mol-1ChemAxon
Polarizability25.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0090000000-4562bd1b09907dc3b700
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uk9-0190000000-0bac3ec6458648a725c0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0fk9-0980000000-91b57386bd019dd7838b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0090000000-938a6d39c487a729e57e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03dl-0090000000-73779217b6427d238ce0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ox-0090000000-13657a0f167139ce56f3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0h2f-0090000000-def6112d5472cfde4da7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fk9-0190000000-56e0b22aa033cf49c8c0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0fk9-0980000000-e04498a4742bec91275e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ufs-2900000000-068e7a9b1ae656d70d01
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f92-9800000000-b99a0e425235a9128533
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0f6t-9300000000-164deed4d2600172d871
MS/MS Spectrum - , positiveLC-MS/MSsplash10-01ox-0090000000-7b3c06efa7853de57efb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ukc-2690000000-7afb48e267c7b334213b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0090000000-9604f2662310bea2bfe7

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
  1. 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]
  2. 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]
  3. Determination of the inhibitory potential of 6 fluoroquinolones on CYP1A2 and CYP2C9 in human liver microsomes [File]
  4. FDA label, ciprofloxacin [File]

Drug created on June 09, 2014 16:39 / Updated on February 21, 2021 18:52