NAV

Nesbuvir

Identification

Generic Name
Nesbuvir
DrugBank Accession Number
DB07238
Background

Nesbuvir has been investigated for the treatment of Hepatitis C.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 446.492
Monoisotopic: 446.131170751
Chemical Formula
C22H23FN2O5S
Synonyms
  • Nesbuvir
External IDs
  • HCV 796
  • HCV-796
  • HCV796

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot AvailableHepatitis C virus genotype 1b (isolate BK)
UGenome polyproteinNot 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
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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 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
2-arylbenzofuran flavonoids
Sub Class
Not Available
Direct Parent
2-arylbenzofuran flavonoids
Alternative Parents
Lignans, neolignans and related compounds / 2-phenylbenzofurans / Sulfanilides / Furan-3-carboxylic acid and derivatives / Fluorobenzenes / Aryl fluorides / Organosulfonamides / Organic sulfonamides / Heteroaromatic compounds / Aminosulfonyl compounds
show 8 more
Substituents
2-arylbenzofuran flavonoid / 2-phenylbenzofuran / Alcohol / Alkanolamine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Benzenoid / Benzofuran
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
EYK815W3Z8
CAS number
691852-58-1
InChI Key
WTDWVLJJJOTABN-UHFFFAOYSA-N
InChI
InChI=1S/C22H23FN2O5S/c1-24-22(27)20-17-11-16(13-3-4-13)18(25(9-10-26)31(2,28)29)12-19(17)30-21(20)14-5-7-15(23)8-6-14/h5-8,11-13,26H,3-4,9-10H2,1-2H3,(H,24,27)
IUPAC Name
5-cyclopropyl-2-(4-fluorophenyl)-6-[N-(2-hydroxyethyl)methanesulfonamido]-N-methyl-1-benzofuran-3-carboxamide
SMILES
CNC(=O)C1=C(OC2=CC(N(CCO)S(C)(=O)=O)=C(C=C12)C1CC1)C1=CC=C(F)C=C1

References

Synthesis Reference

Mannching Ku, Weiyi Li, "PHARMACEUTICAL FORMULATIONS CONTAINING 5-CYCLOPROPYL-2-(4-FLUOROPHENYL)-6-[(2-HYDROXYETHYL)(METHYLSULFONYL)AMINO]-N-METHYL-1-BENZOFURAN-3-CARBOXAMIDE AND METHOD OF MAKING THE SAME." U.S. Patent US20070128270, issued June 07, 2007.

US20070128270
General References
Not Available
PubChem Compound
11561383
PubChem Substance
99443709
ChemSpider
9736157
ChEMBL
CHEMBL1092581
ZINC
ZINC000030691787
PDBe Ligand
79Z
PDB Entries
4tlr

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHepatitis C Virus (HCV) Infection1
1CompletedNot AvailableHealthy Subjects (HS)1
1CompletedTreatmentHealthy Subjects (HS)3
1CompletedTreatmentHepatic Insufficiency / Hepatitis C Virus (HCV) Infection1

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 Solubility0.0631 mg/mLALOGPS
logP2.34ALOGPS
logP1.6Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.34Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.85 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity114.37 m3·mol-1Chemaxon
Polarizability45.61 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9969
Blood Brain Barrier+0.6361
Caco-2 permeable-0.6272
P-glycoprotein substrateSubstrate0.5345
P-glycoprotein inhibitor INon-inhibitor0.7427
P-glycoprotein inhibitor IINon-inhibitor0.5244
Renal organic cation transporterNon-inhibitor0.8886
CYP450 2C9 substrateSubstrate0.5125
CYP450 2D6 substrateNon-substrate0.7947
CYP450 3A4 substrateSubstrate0.5642
CYP450 1A2 substrateNon-inhibitor0.6231
CYP450 2C9 inhibitorInhibitor0.6085
CYP450 2D6 inhibitorNon-inhibitor0.7817
CYP450 2C19 inhibitorInhibitor0.5164
CYP450 3A4 inhibitorInhibitor0.757
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8983
Ames testNon AMES toxic0.5777
CarcinogenicityNon-carcinogens0.568
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5616 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9697
hERG inhibition (predictor II)Inhibitor0.5579
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

Targets

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Details1. Genome 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
  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]
Details2. Genome polyprotein
Kind
Protein
Organism
Not Available
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
Q9WMX2
Uniprot Name
Genome polyprotein
Molecular Weight
326903.025 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 21:19 / Updated at February 21, 2021 18:52