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

Stem definition	Drug id	CAS RN
Hepatitis Virus C (HVC) protease inhibitors	4172	394730-60-0

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
2.40	g	O

ADMET properties:

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

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Approvals:

Date	Agency	Company	Orphan
May 13, 2011	FDA	MERCK SHARP DOHME

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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

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

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Disease	Relation	SNOMED_ID	DOID
Chronic hepatitis C	indication	128302006
Anemia	contraindication	271737000	DOID:2355
Neutropenic disorder	contraindication	303011007	DOID:1227

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	12.84	acidic
pKa2	13.48	acidic
pKa3	13.89	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent 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

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Cathepsin B	Enzyme	P07858	CATB_HUMAN		IC50	5.21	CHEMBL
Cathepsin L1	Enzyme	P07711	CATL1_HUMAN		IC50	6.12	CHEMBL
Chymase	Enzyme	P23946	CMA1_HUMAN		IC50	7.49	CHEMBL
Lysosomal protective protein	Enzyme	P10619	PPGB_HUMAN	INHIBITOR	IC50	6	IUPHAR
Cathepsin L2	Enzyme	O60911	CATL2_HUMAN		IC50	7.12	CHEMBL
Cathepsin K	Enzyme	P43235	CATK_HUMAN		IC50	7.40	CHEMBL
Cathepsin S	Enzyme	P25774	CATS_HUMAN		IC50	6.92	CHEMBL
Cathepsin F	Enzyme	Q9UBX1	CATF_HUMAN		IC50	5.96	CHEMBL
Neutrophil elastase	Enzyme	P08246	ELNE_HUMAN		IC50	4.77	CHEMBL
Hepatitis C virus serine protease, NS3/NS4A	Enzyme		A3EZI9_9HEPC D2K2A8_9HEPC	INHIBITOR	Ki	8.96	CHEMBL	CHEMBL

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External reference:

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ID	Source
HU5	PDB_CHEM_ID
013772	NDDF
10324367	PUBCHEM_CID
1102129	RXNORM
181444	MMSL
27875	MMSL
4030728	VUID
4030728	VANDF
698183007	SNOMEDCT_US
703961009	SNOMEDCT_US

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Pharmaceutical products:

None