Details of the Drug

General Information of Drug (ID: DMFWJC2)

Drug Name
Boceprevir
Synonyms Victrelis; EBP 520; Sch 503034
Indication
Disease Entry ICD 11 Status REF
Coronavirus Disease 2019 (COVID-19) 1D6Y Investigative [1]
Therapeutic Class
Antiviral Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 519.7
Topological Polar Surface Area (xlogp) 3.1
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 30-60 min [2]
Bioavailability
The bioavailability of drug is 4% [2]
Clearance
The total body clearance of drug is 161 L/h [3]
Elimination
Boceprevir is mainly eliminated in the feces (79%) with a small amount eliminated in the urine (9%) [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 3.4 hours [4]
Metabolism
The drug is metabolized via the aldo-ketoreductase-mediated pathway [4]
Vd
The volume of distribution (Vd) of drug is 772 L [3]
Chemical Identifiers
Formula
C27H45N5O5
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
Canonical 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
Cross-matching ID
PubChem CID
10324367
ChEBI ID
CHEBI:68621
CAS Number
394730-60-0
DrugBank ID
DB08873
TTD ID
D0D1CS
ACDINA ID
D00073

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
COVID-19 3C-like protease (3CLpro) TT1D53B R1AB_SARS2 (3264-3569) Inhibitor [1]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Boceprevir, GC-376, and calpain inhibitors II, XII inhibit SARS-CoV-2 viral replication by targeting the viral main protease. 2020. April 20. doi: https://doi.org/10.1101/2020.04.20.051581
2 NORPROLAC? (quinagolide) Product information
3 An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
4 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5 Coronavirus puts drug repurposing on the fast track. Nat Biotechnol. 2020 Apr;38(4):379-381.