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

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 182.69 39.61 95 1034 252361 50351634
Neutropenia 79.30 39.61 46 1083 147919 50456076

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 214.60 44.64 126 1268 200825 29372308
Dysgeusia 81.63 44.64 33 1361 22641 29550492
Neutropenia 52.91 44.64 46 1348 131665 29441468

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 345.88 35.50 193 2049 378487 64118003
Neutropenia 119.75 35.50 84 2158 239540 64256950
Dysgeusia 93.07 35.50 41 2201 47006 64449484
Ascites 56.69 35.50 32 2210 61969 64434521
Thrombocytopenia 53.10 35.50 51 2191 223750 64272740
Leukopenia 46.84 35.50 34 2208 101208 64395282
Hepatic cirrhosis 42.71 35.50 20 2222 26278 64470212
Pancytopenia 42.40 35.50 37 2205 143272 64353218

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 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