R-Boceprevir

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for R-Boceprevir are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the R-Boceprevir?

The molecule R-Boceprevir presents a molecular formula of C27H45N5O5 and its IUPAC name is (1R,2S,5S)-N-[(2R)-4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl]-3-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide.

R-Boceprevir is a molecule that is being investigated as a potential treatment for hepatitis C. It is a prodrug of boceprevir, which is an inhibitor of the hepatitis C virus NS3/4A protease. R-Boceprevir is being developed by Roche and is in clinical trials..

Hepatitis C is a serious viral infection that can lead to liver damage and death. There is no cure for hepatitis C, and treatment options are limited. Boceprevir is a protease inhibitor that has shown promise in treating hepatitis C..

R-Boceprevir is a prodrug of boceprevir. Prodrugs are inactive compounds that are converted into active compounds in the body. In the case of R-Boceprevir, it is converted into boceprevir in the liver..

Boceprevir is an inhibitor of the hepatitis C virus NS3/4A protease. Proteases are enzymes that break down proteins. The NS3/4A protease is responsible for breaking down proteins needed for the hepatitis C virus to replicate. By inhibiting this protease, boceprevir prevents the virus from replicating..

R-Boceprevir is being developed by Roche. Roche is a global pharmaceutical company with headquarters in Switzerland. The company has a long history of innovation and is committed to developing new treatments for serious diseases..

R-Boceprevir is in clinical trials. Clinical trials are research studies that test the safety and effectiveness of new treatments. R-Boceprevir is currently being tested in a Phase III clinical trial. This is the final stage of testing before a treatment is approved for use by the US Food and Drug Administration (FDA)..

The Phase III clinical trial of R-Boceprevir is enrolling patients with hepatitis C who have not been treated before. The trial is expected to last for 48 weeks..

R-Boceprevir has the potential to be a safe and effective treatment for hepatitis C. If the Phase III clinical trial is successful, R-Boceprevir could be approved for use by the FDA and become available to patients in the United States..

3D structure

Cartesian coordinates

Geometry of R-Boceprevir in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

R-Boceprevir LHHCSNFAOIFYRV-MUPNANLLSA-N chemical compound 2D structure molecule svg
R-Boceprevir

 

Molecule descriptors

 
IUPAC name(1R,2S,5S)-N-[(2R)-4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl]-3-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
InChI codeInChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16+,17-,18-,20+/m0/s1
InChI KeyLHHCSNFAOIFYRV-MUPNANLLSA-N
SMILESCC(C)(C)NC(=O)N[C@H](C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)N[C@H](CC1CCC1)C(=O)C(N)=O)C2(C)C)C(C)(C)C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (1R,2S,5S)-N-((1R)-3-AMINO-1-(CYCLOBUTYLMETHYL)-2,3-DIOXOPROPYL)-3-((2S)-2-((((1,1-DIMETHYLETHYL)AMINO)CARBONYL)AMINO)-3,3-DIMETHYL-1-OXOBUTYL)-6,6-DIMETHYL-3-AZABICYCLO(3.1.0)HEXANE-2-CARBOXAMIDE
  • (1S,4S,5R)-N-((1R)-3-AMINO-1-(CYCLOBUTYLMETHYL)-2,3-DIOXO-PROPYL)-3-((2S)-2-(TERT-BUTYLCARBAMOYLAMINO)-3,3-DIMETHYL-BUTANOYL)-6,6-DIMETHYL-3-AZABICYCLO(3.1.0)HEXANE-4-CARBOXAMIDE
  • 3-Azabicyclo(3.1.0)hexane-2-carboxamide, N-((1R)-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)-
  • 569677-41-4
  • BOCEPREVIR METABOLITE (SCH534129)
  • D92PVZ9T6F
  • R-Boceprevir
  • SCH534129
  • Sch 534129
  • Sch-534129

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC14210457
  • UNII-D92PVZ9T6F
  • CHEMBL3542272
  • SCHEMBL785184

Physico-Chemical properties

IUPAC name(1R,2S,5S)-N-[(2R)-4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl]-3-[(2S)-2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
Molecular formulaC27H45N5O5
Molecular weight519.677
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity144.39
LogP3.5
Topological polar surface area150.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.