Nesbuvir
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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
- 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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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AGenome polyprotein inhibitorUGenome polyprotein Not Available Hepatitis C virus genotype 1b (isolate BK) UGenome polyprotein Not 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
- 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 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
- External Links
- PubChem Compound
- 11561383
- PubChem Substance
- 99443709
- ChemSpider
- 9736157
- ChEMBL
- CHEMBL1092581
- ZINC
- ZINC000030691787
- PDBe Ligand
- 79Z
- PDB Entries
- 4tlr
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Treatment Hepatitis C Virus (HCV) Infection 1 somestatus stop reason just information to hide 1 Completed Not Available Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 1 Completed Treatment Healthy Volunteers (HV) 3 somestatus stop reason just information to hide 1 Completed Treatment Hepatic Insufficiency / Hepatitis C Virus (HCV) Infection 1 somestatus stop reason just information to hide
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 0.0631 mg/mL ALOGPS logP 2.34 ALOGPS logP 1.6 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 15.34 Chemaxon pKa (Strongest Basic) -1.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 99.85 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 114.37 m3·mol-1 Chemaxon Polarizability 45.61 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9969 Blood Brain Barrier + 0.6361 Caco-2 permeable - 0.6272 P-glycoprotein substrate Substrate 0.5345 P-glycoprotein inhibitor I Non-inhibitor 0.7427 P-glycoprotein inhibitor II Non-inhibitor 0.5244 Renal organic cation transporter Non-inhibitor 0.8886 CYP450 2C9 substrate Substrate 0.5125 CYP450 2D6 substrate Non-substrate 0.7947 CYP450 3A4 substrate Substrate 0.5642 CYP450 1A2 substrate Non-inhibitor 0.6231 CYP450 2C9 inhibitor Inhibitor 0.6085 CYP450 2D6 inhibitor Non-inhibitor 0.7817 CYP450 2C19 inhibitor Inhibitor 0.5164 CYP450 3A4 inhibitor Inhibitor 0.757 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8983 Ames test Non AMES toxic 0.5777 Carcinogenicity Non-carcinogens 0.568 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5616 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9697 hERG inhibition (predictor II) Inhibitor 0.5579
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0001900000-68bd211d1e920e16dd6b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-01ot-1002900000-a5d0b66b40c62501693c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00mt-7205900000-1f7a630e356bd4afa2f7 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00rb-0009600000-5d305dec9987332f9cd5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-054k-5149300000-ea7e399464e4276dae50 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-1089000000-b29db368d82846209a01 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]- 203.47234 predictedDeepCCS 1.0 (2019) [M+H]+ 205.8679 predictedDeepCCS 1.0 (2019) [M+Na]+ 211.78044 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsGenome polyprotein
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Mature core protein Packages viral RNA to form a viral nucleocapsid, and promotes virion budding (Probable). Participates in the viral particle production as a result of its interaction with the non-structural protein 5A (By similarity). Binds RNA and may function as a RNA chaperone to induce the RNA structural rearrangements taking place during virus replication (By similarity). Modulates viral translation initiation by interacting with viral IRES and 40S ribosomal subunit (By similarity). Affects various cell signaling pathways, host immunity and lipid metabolism (Probable). Prevents the establishment of cellular antiviral state by blocking the interferon-alpha/beta (IFN-alpha/beta) and IFN-gamma signaling pathways and by blocking the formation of phosphorylated STAT1 and promoting ubiquitin-mediated proteasome-dependent degradation of STAT1 (By similarity). Activates STAT3 leading to cellular transformation (By similarity). Regulates the activity of cellular genes, including c-myc and c-fos (PubMed:8533458). May repress the promoter of p53, and sequester CREB3 and SP110 isoform 3/Sp110b in the cytoplasm (PubMed:9110985). Represses cell cycle negative regulating factor CDKN1A, thereby interrupting an important check point of normal cell cycle regulation (PubMed:9524287). Targets transcription factors involved in the regulation of inflammatory responses and in the immune response: suppresses TNF-induced NF-kappa-B activation, and activates AP-1 (PubMed:9811706). Binds to dendritic cells (DCs) via C1QR1, resulting in down-regulation of T-lymphocytes proliferation (By similarity). Alters lipid metabolism by interacting with hepatocellular proteins involved in lipid accumulation and storage (By similarity). Induces up-regulation of FAS promoter activity, and thereby contributes to the increased triglyceride accumulation in hepatocytes (steatosis) (By similarity).
- Specific Function
- ATP binding
- Gene Name
- Not Available
- Uniprot ID
- P26664
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 327198.77 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsGenome polyprotein
- Kind
- Protein
- Organism
- Hepatitis C virus genotype 1b (isolate BK)
- Pharmacological action
- Unknown
- General Function
- Mature core protein Packages viral RNA to form a viral nucleocapsid, and promotes virion budding (Probable). Participates in the viral particle production as a result of its interaction with the non-structural protein 5A (By similarity). Binds RNA and may function as a RNA chaperone to induce the RNA structural rearrangements taking place during virus replication (Probable). Modulates viral translation initiation by interacting with viral IRES and 40S ribosomal subunit (By similarity). Affects various cell signaling pathways, host immunity and lipid metabolism (Probable). Prevents the establishment of cellular antiviral state by blocking the interferon-alpha/beta (IFN-alpha/beta) and IFN-gamma signaling pathways and by blocking the formation of phosphorylated STAT1 and promoting ubiquitin-mediated proteasome-dependent degradation of STAT1 (By similarity). Activates STAT3 leading to cellular transformation (By similarity). Regulates the activity of cellular genes, including c-myc and c-fos (By similarity). May repress the promoter of p53, and sequester CREB3 and SP110 isoform 3/Sp110b in the cytoplasm (By similarity). Represses cell cycle negative regulating factor CDKN1A, thereby interrupting an important check point of normal cell cycle regulation (By similarity). Targets transcription factors involved in the regulation of inflammatory responses and in the immune response: suppresses NF-kappa-B activation, and activates AP-1 (By similarity). Binds to dendritic cells (DCs) via C1QR1, resulting in down-regulation of T-lymphocytes proliferation (By similarity). Alters lipid metabolism by interacting with hepatocellular proteins involved in lipid accumulation and storage (By similarity). Induces up-regulation of FAS promoter activity, and thereby contributes to the increased triglyceride accumulation in hepatocytes (steatosis) (By similarity).
- Specific Function
- ATP binding
- 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]
3. DetailsGenome polyprotein
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Unknown
- General Function
- Mature core protein Packages viral RNA to form a viral nucleocapsid, and promotes virion budding (Probable). Participates in the viral particle production as a result of its interaction with the non-structural protein 5A (By similarity). Binds RNA and may function as a RNA chaperone to induce the RNA structural rearrangements taking place during virus replication (By similarity). Modulates viral translation initiation by interacting with viral IRES and 40S ribosomal subunit (By similarity). Affects various cell signaling pathways, host immunity and lipid metabolism (Probable). Prevents the establishment of cellular antiviral state by blocking the interferon-alpha/beta (IFN-alpha/beta) and IFN-gamma signaling pathways and by blocking the formation of phosphorylated STAT1 and promoting ubiquitin-mediated proteasome-dependent degradation of STAT1 (By similarity). Activates STAT3 leading to cellular transformation (By similarity). Regulates the activity of cellular genes, including c-myc and c-fos (By similarity). May repress the promoter of p53, and sequester CREB3 and SP110 isoform 3/Sp110b in the cytoplasm (By similarity). Represses cell cycle negative regulating factor CDKN1A, thereby interrupting an important check point of normal cell cycle regulation (By similarity). Targets transcription factors involved in the regulation of inflammatory responses and in the immune response: suppresses NF-kappa-B activation, and activates AP-1 (By similarity). Binds to dendritic cells (DCs) via C1QR1, resulting in down-regulation of T-lymphocytes proliferation (By similarity). Alters lipid metabolism by interacting with hepatocellular proteins involved in lipid accumulation and storage (By similarity). Induces up-regulation of FAS promoter activity, and thereby contributes to the increased triglyceride accumulation in hepatocytes (steatosis) (By similarity).
- Specific Function
- ATP binding
- Gene Name
- Not Available
- Uniprot ID
- Q9WMX2
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 326903.025 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 21:19 / Updated at August 26, 2024 19:22