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SML3137

Sigma-Aldrich

Boceprevir

≥98% (HPLC)

Synonym(s):

(1R,2S,5S)-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-3-azabicyclo[3.1.0]hexane-2-carboxamide, (1R,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide, SCH 503034, SCH503034

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About This Item

Empirical Formula (Hill Notation):
C27H45N5O5
CAS Number:
Molecular Weight:
519.68
MDL number:
UNSPSC Code:
12352107
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(N1C[C@@]([H])([C@]2([C@]1(C(NC(CC3CCC3)C(C(N)=O)=O)=O)[H])[H])C2(C)C)[C@](C(C)(C)C)(NC(NC(C)(C)C)=O)[H]

InChI

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 key

LHHCSNFAOIFYRV-DOVBMPENSA-N

Biochem/physiol Actions

Boceprevir is an orally bioavailable, potent and selective hepatitis C virus (HCV) NS3 protease inhibitor (Ki = 14 nM; cell-based replicon assay IC50 = 350 nM).

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


Certificates of Analysis (COA)

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Chunlong Ma et al.
Cell research, 30(8), 678-692 (2020-06-17)
A new coronavirus SARS-CoV-2, also called novel coronavirus 2019 (2019-nCoV), started to circulate among humans around December 2019, and it is now widespread as a global pandemic. The disease caused by SARS-CoV-2 virus is called COVID-19, which is highly contagious
Xiao Tong et al.
Antiviral research, 77(3), 177-185 (2008-01-19)
An issue of clinical importance in the development of new antivirals for HCV is emergence of resistance. Several resistance loci to ketoamide inhibitors of the NS3/4A protease have been identified (residues V36, T54, R155, A156, and V170) by replicon and
Srikanth Venkatraman et al.
Journal of medicinal chemistry, 49(20), 6074-6086 (2006-09-29)
Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-alpha or polyethylene glycol (PEG)-interferon-alpha alone
Andrew J Prongay et al.
Journal of medicinal chemistry, 50(10), 2310-2318 (2007-04-21)
The structures of both the native holo-HCV NS3/4A protease domain and the protease domain with a serine 139 to alanine (S139A) mutation were solved to high resolution. Subsequently, structures were determined for a series of ketoamide inhibitors in complex with
B A Malcolm et al.
Antimicrobial agents and chemotherapy, 50(3), 1013-1020 (2006-02-24)
Cleavage of the hepatitis C virus (HCV) polyprotein by the viral NS3 protease releases functional viral proteins essential for viral replication. Recent studies by Foy and coworkers strongly suggest that NS3-mediated cleavage of host factors may abrogate cellular response to

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