ChemSpider 2D Image | Boceprevir | C27H45N5O5

Boceprevir

  • Molecular FormulaC27H45N5O5
  • Average mass519.677 Da
  • Monoisotopic mass519.342041 Da
  • ChemSpider ID8499830
  • defined stereocentres - 4 of 5 defined stereocentres


More details:



Featured data source



Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(1R,2S,5S)-N-(4-Amino-1-cyclobutyl-3,4-dioxo-2-butanyl)-6,6-dimethyl-3-{3-methyl-N-[(2-methyl-2-propanyl)carbamoyl]-L-valyl}-3-azabicyclo[3.1.0]hexan-2-carboxamid [German] [ACD/IUPAC Name]
(1R,2S,5S)-N-(4-Amino-1-cyclobutyl-3,4-dioxo-2-butanyl)-6,6-dimethyl-3-{3-methyl-N-[(2-methyl-2-propanyl)carbamoyl]-L-valyl}-3-azabicyclo[3.1.0]hexane-2-carboxamide [ACD/IUPAC Name]
(1R,2S,5S)-N-(4-Amino-1-cyclobutyl-3,4-dioxo-2-butanyl)-6,6-diméthyl-3-{3-méthyl-N-[(2-méthyl-2-propanyl)carbamoyl]-L-valyl}-3-azabicyclo[3.1.0]hexane-2-carboxamide [French] [ACD/IUPAC Name]
(1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[N-(tert-butylcarbamoyl)-3-methyl-L-valyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
394730-60-0 [RN]
3-Azabicyclo[3.1.0]hexane-2-carboxamide, N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-, (1R,2S,5S)- [ACD/Index Name]
8840
89BT58KELH
boceprevir [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

SCH 503034 [DBID]
SCH503034 [DBID]
SCH-503034 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      J05AE12 Wikidata Q410551
    • Chemical Class:

      A synthetic tripeptide consisting of <element>N</element>-(<ital>tert</ital>-butylcarbamoyl)-3-methyl-<stereo>L</stereo>-valyl, a cyclopropyl-fused prolyl and 3-amino-4-cyclobutyl-2-oxobutanamide resi dues joined in sequence. Used for treatment of chronic hepatitis C virus genotype 1 infection. ChEBI CHEBI:68621
      A synthetic tripeptide consisting of N-(tert-butylcarbamoyl)-3-methyl-L-valyl, a cyclopropyl-fused prolyl and 3-amino-4-cyclobutyl-2-oxobutanamide resi; dues joined in sequence. Used for treatment of chronic hepatitis C virus genotype 1 infection. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68621
    • Bio Activity:

      Anti-infection MedChem Express HY-10237
      Anti-infection; Metabolism/Protease; MedChem Express HY-10237
      Boceprevir(EBP-520, SCH503034) is an HCV protease inhibitor (Ki=14 nM) for the treatment of hepatitis C virus infection. MedChem Express
      Boceprevir(EBP-520, SCH503034) is an HCV protease inhibitor (Ki=14 nM) for the treatment of hepatitis C virus infection.; IC50 Value: 14 nM (Ki); Target: HCV; Boceprevir is a potent inhibitor in both enzyme assay (Ki* = 14 nM) and cell-based replicon assay (EC 90 = 0.35 microM). MedChem Express HY-10237
      Boceprevir(EBP-520, SCH503034) is an HCV protease inhibitor (Ki=14 nM) for the treatment of hepatitis C virus infection.;IC50 Value: 14 nM (Ki);Target: HCVBoceprevir is a potent inhibitor in both enzyme assay (Ki* = 14 nM) and cell-based replicon assay (EC 90 = 0.35 microM). It is highly selective (2200x) against human neutrophil elastase (HNE). Boceprevir is well tolerated in humans and demonstrated antiviral activity in phase I clinical trials. It is currently in phase II trials. This Account details the complexity and challenges encountered in the drug discovery process. ;Treatment with Boceprevir triple therapy increased SVR to 63-66% compared to 38% receiving PEG-IFN/RBV therapy. Non-Black patients achieved higher SVR rates compared to Black patients. Responsiveness to interferon in the lead-in phase was predictive for SVR. SVR rates did not differ between patients randomized to RGT with Boceprevir and those treated with a fixed duration. Anaemia was the most important adver MedChem Express HY-10237
      HCV MedChem Express HY-10237
      HCV HCV NS3/4A Protease MedChem Express HY-10237

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.2±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.533
Molar Refractivity: 138.7±0.3 cm3
#H bond acceptors: 10
#H bond donors: 5
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 3
ACD/LogP: 2.05
ACD/LogD (pH 5.5): 2.40
ACD/BCF (pH 5.5): 39.08
ACD/KOC (pH 5.5): 479.56
ACD/LogD (pH 7.4): 2.40
ACD/BCF (pH 7.4): 39.08
ACD/KOC (pH 7.4): 479.56
Polar Surface Area: 151 Å2
Polarizability: 55.0±0.5 10-24cm3
Surface Tension: 46.4±3.0 dyne/cm
Molar Volume: 446.9±3.0 cm3

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