1-(2-CYCLOPROPYLETHYL)-3-(1,1-DIOXIDO-2H-1,2,4-BENZOTHIADIAZIN-3-YL)-6-FLUORO-4-HYDROXYQUINOLIN-2(1H)-ONE

Identification

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Name
1-(2-CYCLOPROPYLETHYL)-3-(1,1-DIOXIDO-2H-1,2,4-BENZOTHIADIAZIN-3-YL)-6-FLUORO-4-HYDROXYQUINOLIN-2(1H)-ONE
Accession Number
DB08278
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 427.449
Monoisotopic: 427.100204974
Chemical Formula
C21H18FN3O4S
InChI Key
QEMCDXCXSVPAAB-UHFFFAOYSA-N
InChI
InChI=1S/C21H18FN3O4S/c22-13-7-8-16-14(11-13)19(26)18(21(27)25(16)10-9-12-5-6-12)20-23-15-3-1-2-4-17(15)30(28,29)24-20/h1-4,7-8,11-12,26H,5-6,9-10H2,(H,23,24)
IUPAC Name
3-[1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-2H-1λ⁶,2,4-benzothiadiazine-1,1-dione
SMILES
OC1=C(C(=O)N(CCC2CC2)C2=C1C=C(F)C=C2)C1=NC2=CC=CC=C2S(=O)(=O)N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHepatitis C virus genotype 1b (isolate BK)
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
Toxicity
Not Available
Affected organisms
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.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5273394
PubChem Substance
99444749
ChemSpider
20114428
BindingDB
50181559
ChEMBL
CHEMBL372357
HET
NN2
PDB Entries
2giq

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0205 mg/mLALOGPS
logP2.45ALOGPS
logP2.34ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)5.74ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.07 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.02 m3·mol-1ChemAxon
Polarizability42.6 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9884
Blood Brain Barrier-0.6761
Caco-2 permeable-0.5777
P-glycoprotein substrateSubstrate0.5356
P-glycoprotein inhibitor INon-inhibitor0.6522
P-glycoprotein inhibitor IIInhibitor0.7975
Renal organic cation transporterNon-inhibitor0.7411
CYP450 2C9 substrateNon-substrate0.5827
CYP450 2D6 substrateNon-substrate0.8056
CYP450 3A4 substrateNon-substrate0.5594
CYP450 1A2 substrateNon-inhibitor0.6657
CYP450 2C9 inhibitorNon-inhibitor0.5231
CYP450 2D6 inhibitorNon-inhibitor0.8457
CYP450 2C19 inhibitorNon-inhibitor0.607
CYP450 3A4 inhibitorNon-inhibitor0.6175
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6065
Ames testNon AMES toxic0.6163
CarcinogenicityNon-carcinogens0.6354
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5134 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9587
hERG inhibition (predictor II)Inhibitor0.5165
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as fluoroquinolones. These are compounds containing a fluorine atom attached to a quinolone. Quinolone or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine, and bears a ketone group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Quinolones and derivatives
Direct Parent
Fluoroquinolones
Alternative Parents
1,2,4-benzothiadiazine-1,1-dioxides / Haloquinolines / Hydroquinolones / Hydroxyquinolines / Hydroquinolines / Pyridinones / Hydroxypyridines / Benzenoids / Imidolactams / Aryl fluorides
show 12 more
Substituents
Fluoroquinolone / 1,2,4-benzothiadiazine-1,1-dioxide / Haloquinoline / Dihydroquinolone / Hydroxyquinoline / Benzothiadiazine / Dihydroquinoline / Hydroxypyridine / Pyridinone / Aryl fluoride
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Hepatitis C virus genotype 1b (isolate BK)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Core protein packages viral RNA to form a viral nucleocapsid, and promotes virion budding. Modulates viral translation initiation by interacting with HCV IRES and 40S ribosomal subunit. Also regula...
Gene Name
Not Available
Uniprot ID
P26663
Uniprot Name
Genome polyprotein
Molecular Weight
327190.435 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:30 / Updated on November 02, 2019 02:22