1-(2-cyclopropylethyl)-3-(1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-2(1H)-quinolinone
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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
Target Actions Organism UGenome polyprotein Not Available Hepatitis 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
- 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.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
- External Links
- PubChem Compound
- 5273394
- PubChem Substance
- 99444749
- ChemSpider
- 20114428
- BindingDB
- 50181559
- ChEMBL
- CHEMBL372357
- ZINC
- ZINC000100036569
- PDBe Ligand
- NN2
- PDB Entries
- 2giq
Clinical Trials
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
Property Value Source Water Solubility 0.0225 mg/mL ALOGPS logP 3.08 ALOGPS logP 2.2 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 5.79 Chemaxon pKa (Strongest Basic) -2.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 99.07 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 110.59 m3·mol-1 Chemaxon Polarizability 42.56 Å3 Chemaxon Number of Rings 5 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
Property Value Probability Human Intestinal Absorption + 0.9884 Blood Brain Barrier - 0.6761 Caco-2 permeable - 0.5777 P-glycoprotein substrate Substrate 0.5356 P-glycoprotein inhibitor I Non-inhibitor 0.6522 P-glycoprotein inhibitor II Inhibitor 0.7975 Renal organic cation transporter Non-inhibitor 0.7411 CYP450 2C9 substrate Non-substrate 0.5827 CYP450 2D6 substrate Non-substrate 0.8056 CYP450 3A4 substrate Non-substrate 0.5594 CYP450 1A2 substrate Non-inhibitor 0.6657 CYP450 2C9 inhibitor Non-inhibitor 0.5231 CYP450 2D6 inhibitor Non-inhibitor 0.8457 CYP450 2C19 inhibitor Non-inhibitor 0.607 CYP450 3A4 inhibitor Non-inhibitor 0.6175 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6065 Ames test Non AMES toxic 0.6163 Carcinogenicity Non-carcinogens 0.6354 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5134 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9587 hERG inhibition (predictor II) Inhibitor 0.5165
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0000900000-5cedbf6c82083c8e9bdf Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-4004900000-13285ff47cc82f020e50 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-1009000000-0fd2cca07fa06c48f4ca Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-3000900000-f1ca8f5bd6f5e626b7c4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-07i2-1109000000-fc5b2a815f7bff391e87 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03fr-4319500000-bbcf1250b942a4307bf0 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.77953 predictedDeepCCS 1.0 (2019) [M+H]+ 188.13753 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.2307 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGenome polyprotein
- 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
- 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