Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0218)
Drug Name
Boceprevir
Synonyms
Boceprevir; Victrelis; EBP 520; SCH 503034; SCH-503034; (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[N-(tert-butylcarbamoyl)-3-methyl-L-valyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide; 3-{[(1R,2S,5S)-3-[(2S)-2-[(tert-butylcarbamoyl)amino]-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2-yl]formamido}-4-cyclobutyl-2-oxobutanamide; 394730-60-0; 89BT58KELH; CHEBI:68621; UNII-89BT58KELH
Indication Viral hepatitis [ICD11: 1E51] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 519.7 Topological Polar Surface Area 151
Heavy Atom Count 37 Rotatable Bond Count 10
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
10324367
PubChem SID
15333889 ; 22433429 ; 22693607 ; 41390184 ; 46512784 ; 57374555 ; 57414843 ; 79603721 ; 92309409 ; 96025559 ; 103500897 ; 109692987 ; 134348397 ; 135216213 ; 137186019 ; 137251857 ; 139040316 ; 152258143 ; 160645839 ; 160646982 ; 162256796 ; 163667336 ; 164837112 ; 175427026 ; 175427127 ; 176245990 ; 180371765 ; 198992422 ; 223366205 ; 223669397 ; 226940314 ; 245972903 ; 249582863 ; 251970943 ; 252076908
ChEBI ID
CHEBI:68621
CAS Number
394730-60-0
TTD Drug ID
D0V3YT
Formula
C27H45N5O5
Canonical SMILES
CC1(C2C1C(N(C2)C(=O)C(C(C)(C)C)NC(=O)NC(C)(C)C)C(=O)NC(CC3CCC3)C(=O)C(=O)N)C
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Boceprevir metabolite M28 DM006335
71316139
Multi-steps Reaction - Oxidationn; keto-reduction 1 [4]
Boceprevir metabolite M31 DM006336
156596465
Multi-steps Reaction - Oxidationn; keto-reduction 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006805 Boceprevir Boceprevir metabolite M28 Multi-steps Reaction - Oxidationn; keto-reduction AKR1C2 ... [4]
MR006806 Boceprevir Boceprevir metabolite M31 Multi-steps Reaction - Oxidationn; keto-reduction AKR1C2 ... [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
References
1 Boceprevir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetic evaluation of the interaction between hepatitis C virus protease inhibitor boceprevir and 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors atorvastatin and pravastatin. Antimicrob Agents Chemother. 2013 Jun;57(6):2582-8.
3 Direct-acting antiviral agents for hepatitis C virus infection. Annu Rev Pharmacol Toxicol. 2013;53:427-49.
4 Characterization of human liver enzymes involved in the biotransformation of boceprevir, a hepatitis C virus protease inhibitor

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