Boceprevir

CAT: 0804-HY-10237-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No

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CAT#:0804-HY-10237-02Size:10 mM - 1 mL

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Description

Boceprevir (EBP 520) is a potent, highly selective, orally bioavailable HCV NS3 protease inhibitor with a Ki of 14 nM in both enzyme assay and an EC90 of 350 nM in cell-based replicon assay[1][2][3][4][5]. Boceprevir inhibits SARS-CoV-2 3CLpro activity[6].

CAS Number

394730-60-0

Product Name Alternative

EBP 520; SCH 503034

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

HCV; HCV Protease; SARS-CoV

Type

Reference compound

Related Pathways

Anti-infection; Metabolic Enzyme/Protease

Applications

COVID-19-anti-virus

Field of Research

Infection

Assay Protocol

https://www.medchemexpress.com/Boceprevir.html

Purity

99.0

Solubility

DMSO : 180 mg/mL (ultrasonic)

Smiles

O=C(N1[C@@H]([C@@]2([H])C(C)([C@]2(C1)[H])C)C(NC(C(C(N)=O)=O)CC3CCC3)=O)[C@@H](NC(NC(C)(C)C)=O)C(C)(C)C

Molecular Formula

C27H45N5O5

Molecular Weight

519.68

Precautions

H302, H315, H319, H335

References & Citations

[1]Njoroge FG, et al. Challenges in modern drug discovery: a case study of boceprevir, an HCV protease inhibitor for the treatment of hepatitis C virus infection. Acc Chem Res. 2008 Jan;41 (1) :50-9.|[2]Yao M, et al. Conditional Inducible Triple-Transgenic Mouse Model for Rapid Real-Time Detection of HCV NS3/4A ProteaseActivity. PLoS One. 2016 Mar 4;11 (3) :e0150894.|[3]Coilly A, et al. Practical management of boceprevir and immunosuppressive therapy in liver transplant recipients with hepatitis C virus recurrence. Antimicrob Agents Chemother. 2012 Nov;56 (11) :5728-34.|[4]Berenguer M, et al. New developments in the management of hepatitis C virus infection: focus on boceprevir. Biologics. 2012;6:249-56.|[5]Burton MJ, et al. Telaprevir and boceprevir in african americans with genotype 1 chronic hepatitis C: implications for patients and providers. South Med J. 2012 Aug;105 (8) :431-6.|[6]Qi Sun, et al. Bardoxolone and bardoxolone methyl, two Nrf2 activators in clinical trials, inhibit SARS-CoV-2 replication and its 3C-like protease. Signal Transduct Target Ther. 2021 May 29;6 (1) :212.

Shipping Conditions

Blue Ice

Storage Conditions

-20°C, 3 years (Powder)

Scientific Category

Reference compound1

Clinical Information

Launched

Chemical Information

Boceprevir

Boceprevir is a synthetic tripeptide consisting of N-(tert-butylcarbamoyl)-3-methyl-L-valyl, a cyclopropyl-fused prolyl and 3-amino-4-cyclobutyl-2-oxobutanamide residues joined in sequence. Used for treatment of chronic hepatitis C virus genotype 1 infection. It has a role as an antiviral drug, a peptidomimetic and a hepatitis C protease inhibitor. It is a member of ureas and a tripeptide.

CAS Number	394730-60-0
PubChem CID	10324367
IUPAC Name	(1R,2S,5S)-N-(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 Formula	C27H45N5O5
Molecular Weight	519.7
XLogP	3.1
Topological Polar Surface Area	151
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Heavy Atom Count	37
Formal Charge	0
Complexity	959

SMILES

CC1([C@@H]2[C@H]1[C@H](N(C2)C(=O)[C@H](C(C)(C)C)NC(=O)NC(C)(C)C)C(=O)NC(CC3CCC3)C(=O)C(=O)N)C

InChI

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

InChIKey

LHHCSNFAOIFYRV-DOVBMPENSA-N

Chemical Structure

2D Structure

CAS: 394730-60-0

CID: 10324367

Formula: C27H45N5O5

MW: 519.7

Interactive 3D Structure

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Computed Properties

Property	Value
Molecular Weight	519.7
XLogP3	3.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	10
Exact Mass	519.34206955
Monoisotopic Mass	519.34206955
Topological Polar Surface Area	151 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	959
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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A3261-10	Boceprevir

Boceprevir

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