Nesbuvir

Identification

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Name
Nesbuvir
Accession Number
DB07238  (DB12516)
Type
Small Molecule
Groups
Investigational
Description

Nesbuvir has been investigated for the treatment of Hepatitis C.

Structure
Thumb
Synonyms
Not Available
External IDs
HCV 796 / HCV-796 / HCV796
Categories
UNII
EYK815W3Z8
CAS number
691852-58-1
Weight
Average: 446.492
Monoisotopic: 446.131170751
Chemical Formula
C22H23FN2O5S
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGenome polyproteinNot Available
UGenome polyproteinNot Available
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Not Available
Food Interactions
Not Available

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
External Links
PubChem Compound
11561383
PubChem Substance
99443709
ChemSpider
9736157
ChEMBL
CHEMBL1092581
HET
79Z
PDB Entries
3fqk / 3fql / 4tlr

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentHepatic Insufficiency / Hepatitis C Viral Infection1
2CompletedTreatmentHepatitis C Viral 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)-1.7ChemAxon
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

Taxonomy

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 / Neolignan skeleton / 2-phenylbenzofuran / Phenylbenzofuran / Sulfanilide / Benzofuran / Furoic acid or derivatives / Furan-3-carboxylic acid or derivatives / Fluorobenzene / Halobenzene
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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
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]
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. [PubMed:10592235]

Drug created on September 15, 2010 15:19 / Updated on May 01, 2019 10:18