1-(2-cyclopropylethyl)-3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-2(1H)-quinolinone

Identification

Generic Name
1-(2-cyclopropylethyl)-3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-2(1H)-quinolinone
DrugBank Accession Number
DB08278
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 427.449
Monoisotopic: 427.100204974
Chemical Formula
C21H18FN3O4S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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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

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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2,4-benzothiadiazine-1,1-dioxide / Amidine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Benzothiadiazine / Dihydroquinoline / Dihydroquinolone
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
477931-14-9
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]-4H-1lambda6,2,4-benzothiadiazine-1,1-dione
SMILES
OC1=C(C(=O)N(CCC2CC2)C2=C1C=C(F)C=C2)C1=NS(=O)(=O)C2=C(N1)C=CC=C2

References

General References
Not Available
PubChem Compound
5273394
PubChem Substance
99444749
ChemSpider
20114428
BindingDB
50181559
ChEMBL
CHEMBL372357
ZINC
ZINC000100036569
PDBe Ligand
NN2
PDB Entries
2giq

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0225 mg/mLALOGPS
logP3.08ALOGPS
logP2.2Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)5.79Chemaxon
pKa (Strongest Basic)-2.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.07 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity110.59 m3·mol-1Chemaxon
Polarizability42.56 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/MSsplash10-004i-0000900000-5cedbf6c82083c8e9bdf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-4004900000-13285ff47cc82f020e50
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1009000000-0fd2cca07fa06c48f4ca
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-3000900000-f1ca8f5bd6f5e626b7c4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-07i2-1109000000-fc5b2a815f7bff391e87
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fr-4319500000-bbcf1250b942a4307bf0
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]-185.77953
predicted
DeepCCS 1.0 (2019)
[M+H]+188.13753
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.2307
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at September 15, 2010 21:30 / Updated at June 12, 2020 16:52