boceprevir 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
Hepatitis Virus C (HVC) protease inhibitors 4172 394730-60-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • boceprevir
  • victrelis
  • SCH 503034
Boceprevir is an inhibitor of the HCV NS3/4A protease that is necessary for the proteolytic cleavage of the HCV encoded polyprotein into mature forms of the NS4A, NS4B, NS5A and NS5B proteins. Boceprevir covalently, yet reversibly, binds to the NS3 protease active site serine (S139) through an (alpha)-ketoamide functional group to inhibit viral replication in HCV-infected host cells. In a biochemical assay, boceprevir inhibited the activity of recombinant HCV genotype 1a and 1b NS3/4A protease enzymes, with Ki values of 14 nM for each subtype.
  • Molecular weight: 519.69
  • Formula: C27H45N5O5
  • CLOGP: 3.36
  • LIPINSKI: 1
  • HAC: 10
  • HDO: 4
  • TPSA: 150.70
  • ALOGS: -4.35
  • ROTB: 10
  • Status: OFM
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
S (Water solubility) 1.50 mg/mL Bocci G, Oprea TI, Benet LZ

Approvals:

DateAgencyCompanyOrphan
May 13, 2011 FDA MERCK SHARP DOHME

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaemia 197.21 39.35 98 1047 293332 63194545
Neutropenia 81.22 39.35 46 1099 174959 63312918

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaemia 216.51 45.56 126 1270 233209 34722326
Dysgeusia 81.95 45.56 33 1363 26464 34929071
Neutropenia 52.57 45.56 46 1350 156732 34798803

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anaemia 362.03 37.03 196 2064 444819 79297309
Neutropenia 121.36 37.03 84 2176 287626 79454502
Dysgeusia 93.43 37.03 41 2219 57136 79684992
Ascites 56.88 37.03 32 2228 75530 79666598
Thrombocytopenia 54.58 37.03 51 2209 265208 79476920
Leukopenia 48.79 37.03 34 2226 116479 79625649
Pancytopenia 44.30 37.03 37 2223 165708 79576420
Hepatic cirrhosis 41.20 37.03 20 2240 34886 79707242

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J05AP03 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HCV infections
FDA MoA N0000182141 Cytochrome P450 3A4 Inhibitors
FDA MoA N0000182638 HCV NS3/4A Protease Inhibitors
FDA EPC N0000182639 Hepatitis C Virus NS3/4A Protease Inhibitor
FDA MoA N0000190115 Cytochrome P450 3A5 Inhibitors
CHEBI has role CHEBI:36044 antiviral drugs
CHEBI has role CHEBI:63175 peptidomimetics
CHEBI has role CHEBI:64924 hepatitis C protease inhibitors

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Chronic hepatitis C indication 128302006
Anemia contraindication 271737000 DOID:2355
Neutropenic disorder contraindication 303011007 DOID:1227




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.84 acidic
pKa2 13.48 acidic
pKa3 13.89 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
200MG VICTRELIS MERCK SHARP DOHME N202258 May 13, 2011 DISCN CAPSULE ORAL RE43298 Dec. 22, 2024 TREATMENT OF CHRONIC HEPATITIS C (CHC) GENOTYPE 1 INFECTION IN COMBINATION WITH PEGINTERFERON ALFA AND RIBAVIRIN IN ADULT PATIENTS (>=18 YEARS OF AGE) WITH COMPENSATED LIVER DISEASE
200MG VICTRELIS MERCK SHARP DOHME N202258 May 13, 2011 DISCN CAPSULE ORAL 8119602 March 17, 2027 TREATMENT OF CHRONIC HEPATITIS C (CHC) GENOTYPE 1 INFECTION, ADMINISTERED WITH FOOD
200MG VICTRELIS MERCK SHARP DOHME N202258 May 13, 2011 DISCN CAPSULE ORAL 7772178 Nov. 11, 2027 TREATMENT OF CHRONIC HEPATITIS C (CHC) GENOTYPE 1 INFECTION IN COMBINATION WITH PEGINTERFERON ALFA AND RIBAVIRIN IN ADULT PATIENTS (>=18 YEARS OF AGE) WITH COMPENSATED LIVER DISEASE

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Cathepsin B Enzyme IC50 5.21 CHEMBL
Cathepsin L1 Enzyme IC50 6.12 CHEMBL
Chymase Enzyme IC50 7.49 CHEMBL
Lysosomal protective protein Enzyme INHIBITOR IC50 6 IUPHAR
Cathepsin L2 Enzyme IC50 7.12 CHEMBL
Cathepsin K Enzyme IC50 7.40 CHEMBL
Cathepsin S Enzyme IC50 6.92 CHEMBL
Cathepsin F Enzyme IC50 5.96 CHEMBL
Neutrophil elastase Enzyme IC50 4.77 CHEMBL
Hepatitis C virus serine protease, NS3/NS4A Enzyme INHIBITOR Ki 8.96 CHEMBL CHEMBL
Nonstructural protein NS3-4A Unclassified Ki 7.85 CHEMBL
Replicase polyprotein 1ab Enzyme IC50 5.38 CHEMBL
Replicase polyprotein 1a Unclassified INHIBITOR IC50 6.02 IUPHAR
Genome polyprotein Unclassified Ki 7.85 CHEMBL

External reference:

IDSource
4030728 VUID
N0000182738 NUI
D08876 KEGG_DRUG
4030728 VANDF
C1738934 UMLSCUI
CHEBI:68621 CHEBI
HU5 PDB_CHEM_ID
CHEMBL218394 ChEMBL_ID
DB08873 DRUGBANK_ID
C512204 MESH_SUPPLEMENTAL_RECORD_UI
7876 IUPHAR_LIGAND_ID
8840 INN_ID
89BT58KELH UNII
10324367 PUBCHEM_CID
1102129 RXNORM
181444 MMSL
27875 MMSL
d07774 MMSL
013772 NDDF
698183007 SNOMEDCT_US
703961009 SNOMEDCT_US

Pharmaceutical products:

None