NAV

Flosequinan

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Flosequinan
DrugBank Accession Number
DB13228
Background

Flosequinan was approved in the USA and the UK for a year prior to being withdrawn from the market due to increased mortality in chronic heart failure patients, found in drug trials.1,2

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 239.26
Monoisotopic: 239.041627903
Chemical Formula
C11H10FNO2S
Synonyms
  • Flosequinan
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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
Integrate drug-drug
interactions in your software
IloprostIloprost may increase the hypotensive activities of Flosequinan.
Isosorbide mononitrateFlosequinan may increase the vasodilatory activities of Isosorbide mononitrate.
Patent BlueThe therapeutic efficacy of Flosequinan can be decreased when used in combination with Patent Blue.
Food Interactions
Not Available

Categories

ATC Codes
C01DB01 — Flosequinan
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hydroquinolones. These are compounds containing a hydrogenated quinoline bearing a ketone group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinolones and derivatives
Direct Parent
Hydroquinolones
Alternative Parents
Haloquinolines / Hydroquinolines / Aryl fluorides / Benzenoids / Pyridines and derivatives / Vinylogous amides / Heteroaromatic compounds / Sulfoxides / Azacyclic compounds / Sulfinyl compounds
show 6 more
Substituents
Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Dihydroquinoline / Dihydroquinolone / Haloquinoline / Heteroaromatic compound / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6NB119DLU7
CAS number
76568-02-0
InChI Key
UYGONJYYUKVHDD-UHFFFAOYSA-N
InChI
InChI=1S/C11H10FNO2S/c1-13-6-10(16(2)15)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3
IUPAC Name
7-fluoro-3-methanesulfinyl-1-methyl-1,4-dihydroquinolin-4-one
SMILES
CN1C=C(C(=O)C2=C1C=C(F)C=C2)S(C)=O

References

General References
  1. Packer M, Pitt B, Rouleau JL, Swedberg K, DeMets DL, Fisher L: Long-Term Effects of Flosequinan on the Morbidity and Mortality of Patients With Severe Chronic Heart Failure: Primary Results of the PROFILE Trial After 24 Years. JACC Heart Fail. 2017 Jun;5(6):399-407. doi: 10.1016/j.jchf.2017.03.003. Epub 2017 May 10. [Article]
  2. Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
Human Metabolome Database
HMDB0252316
ChemSpider
3672315
RxNav
25089
ChEBI
134972
ChEMBL
CHEMBL1908307
Wikipedia
Flosequinan

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.25 mg/mLALOGPS
logP1.13ALOGPS
logP0.72Chemaxon
logS-1.5ALOGPS
pKa (Strongest Basic)-1.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area37.38 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity63.82 m3·mol-1Chemaxon
Polarizability22.88 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-a4d1cd3ae2df4b7dc9d8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0290000000-e1de1f4dbf06816355be
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-3900000000-6fc5912b06389fae8fba
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-0090000000-50786f6a1c065f10b59a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-5c3bb737b84049c4db12
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-db8a53ece93ec35dcbcb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.83954
predicted
DeepCCS 1.0 (2019)
[M+H]+150.19753
predicted
DeepCCS 1.0 (2019)
[M+Na]+156.32346
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:38 / Updated at December 01, 2022 11:28