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Details

Stereochemistry MIXED
Molecular Formula C27H45N5O5
Molecular Weight 519.6767
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BOCEPREVIR

SMILES

CC(C)(C)NC(=O)N[C@H](C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)NC(CC3CCC3)C(=O)C(N)=O)C2(C)C)C(C)(C)C

InChI

InChIKey=LHHCSNFAOIFYRV-DOVBMPENSA-N
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

HIDE SMILES / InChI
Molecular Formula C27H45N5O5
Molecular Weight 519.6767
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 4 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
123738
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:40:03 UTC 2023
Edited
by admin
on Fri Dec 15 15:40:03 UTC 2023
Record UNII
89BT58KELH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BOCEPREVIR
DASH   EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
BOCEPREVIR [EMA EPAR]
Common Name English
SCH 503034
Code English
BOCEPREVIR [MI]
Common Name English
EBP 520
Code English
BOCEPREVIR [USAN]
Common Name English
BOCEPREVIR [MART.]
Common Name English
boceprevir [INN]
Common Name English
EBP-520
Code English
Boceprevir [WHO-DD]
Common Name English
SCH-503034
Code English
BOCEPREVIR [ORANGE BOOK]
Common Name English
VICTRELIS
Brand Name English
BOCEPREVIR [VANDF]
Common Name English
(1R,2S,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[(1,1-dimethylethyl)carbamoyl]amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
Systematic Name English
3-AZABICYCLO(3.1.0)HEXANE-2-CARBOXAMIDE, N-(3-AMINO-1-(CYCLOBUTYLMETHYL)-2,3-DIOXOPROPYL)-3-((2S)-2-((((1,1-DIMETHYLETHYL)AMINO)CARBONYL)AMINO)-3,3-DIMETHYL-1-OXOBUTYL)-6,6-DIMETHYL-, (1R,2S,5S)-
Systematic Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS VICTRELIS (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
WHO-VATC QJ05AE12
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
WHO-ATC J05AP03
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
LIVERTOX NBK548247
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
WHO-ATC J05AP03
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
NDF-RT N0000182639
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
WHO-ATC J05AE12
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
Code System Code Type Description
CHEBI
68621
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
FDA UNII
89BT58KELH
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID30960103
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
DRUG CENTRAL
4172
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
MERCK INDEX
m2592
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY Merck Index
HSDB
8081
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
LACTMED
Boceprevir
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
INN
8840
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
EVMPD
SUB31579
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
CAS
394730-60-0
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
RXCUI
1102129
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY RxNorm
NDF-RT
N0000182141
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
DRUG BANK
DB08873
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
USAN
N07/04
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
ChEMBL
CHEMBL218394
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
WIKIPEDIA
BOCEPREVIR
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
NCI_THESAURUS
C117292
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
SMS_ID
100000124138
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
PUBCHEM
10324367
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY
NDF-RT
N0000182638
Created by admin on Fri Dec 15 15:40:03 UTC 2023 , Edited by admin on Fri Dec 15 15:40:03 UTC 2023
PRIMARY HCV NS3/4A Protease Inhibitors [MoA]
Related Record Type Details
Structure of (1R,2S,5S)-N-((1S)-3-AMINO-1-(CYCLOBUTYLMETHYL)-2,3-DIOXOPROPYL)-3-((2S)-2-((((1,1-DIMETHYLETHYL)AMINO)CARBONYL)AMINO)-3,3-DIMETHYL-1-OXOBUTYL)-6,6-DIMETHYL-3-AZABICYCLO(3.1.0)HEXANE-2-CARBOXAMIDE
ENANTIOMER->MIXED
MAJOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of BOCEPREVIR
EXCRETED UNCHANGED
Approximately 10% and 32% of the total radioactivity recovered in feces and urine, respectively, was unchanged boceprevir. In the mass balance trial, investigators recovered ~88.2% of the total dose of radioactivity in feces (78.9%) and urine (9.3%).
FECAL
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
moderate and strong inducers of CYP3A4 should not be co-administered due to the potential for loss of efficacy.
HCV NS3-4A SERINE PROTEASE
TARGET -> INHIBITOR
COMPETITIVE INHIBITOR
Structure of R-BOCEPREVIR
ENANTIOMER->MIXED
MAJOR
Structure of BOCEPREVIR
EXCRETED UNCHANGED
Approximately 10% and 32% of the total radioactivity recovered in feces and urine, respectively, was unchanged boceprevir. In the mass balance trial, investigators recovered ~88.2% of the total dose of radioactivity in feces (78.9%) and urine (9.3%).
URINE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
sensitive substrates of CYP3A4 with a narrow therapeutic index should not be coadministered.
STRONG
ALDO-KETO REDUCTASE FAMILY 1 MEMBER C3
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of (1S,4S,5R)-N-(3-AMINO-1-((3-HYDROXYCYCLOBUTYL)METHYL)-2,3-DIOXO-PROPYL)-3-((2S)-2-(TERT-BUTYLCARBAMOYLAMINO)-3,3-DIMETHYL-BUTANOYL)-6,6-DIMETHYL-3-AZABICYCLO(3.1.0)HEXANE-4-CARBOXAMIDE
METABOLITE -> PARENT
Structure of (1S,4S,5R)-3-((2S)-2-(TERT-BUTYLCARBAMOYLAMINO)-3,3-DIMETHYL-BUTANOYL)-6,6-DIMETHYL-3-AZABICYCLO(3.1.0)HEXANE-4-CARBOXAMIDE
METABOLITE -> PARENT
Structure of (1R,2S,5S)-3-((2S)-2-((((1,1-DIMETHYLETHYL)AMINO)CARBONYL)AMINO)-3,3-DIMETHYL-1-OXOBUTYL)-6,6-DIMETHYL-3-AZABICYCLO(3.1.0)HEXANE-2-CARBOXYLIC ACID
METABOLITE -> PARENT
Structure of (1S,4S,5R)-N-((1R)-3-AMINO-1-(CYCLOBUTYLMETHYL)-2-HYDROXY-3-OXO-PROPYL)-3-((2S)-2-(TERT-BUTYLCARBAMOYLAMINO)-3,3-DIMETHYL-BUTANOYL)-6,6-DIMETHYL-3-AZABICYCLO(3.1.0)HEXANE-4-CARBOXAMIDE
METABOLITE -> PARENT
Structure of (1S,4S,5R)-N-(3-AMINO-1-((1-HYDROXYCYCLOBUTYL)METHYL)-2,3-DIOXO-PROPYL)-3-((2S)-2-(TERT-BUTYLCARBAMOYLAMINO)-3,3-DIMETHYL-BUTANOYL)-6,6-DIMETHYL-3-AZABICYCLO(3.1.0)HEXANE-4-CARBOXAMIDE
METABOLITE -> PARENT
Structure of (2S)-2-(TERT-BUTYLAMINOCARBONYLAMINO)-3,3-DIMETHYLBUTANOIC ACID
METABOLITE -> PARENT
Related Record Type Details
Structure of BOCEPREVIR
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC single dose

Blood to plasma ratio PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
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