boceprevir

CHEBI:68621 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A synthetic tripeptide consisting of N-(tert-butylcarbamoyl)-3-methyl-L-valyl, a cyclopropyl-fused prolyl and 3-amino-4-cyclobutyl-2-oxobutanamide residues joined in sequence. Used for treatment of chronic hepatitis C virus genotype 1 infection. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:47857
Label unavailable CHEBI:47923

Chemical structure

Computed structure properties
Molecular formula	C27H45N5O5
Charge	0
Average mass	519.687 Da
Monoisotopic mass	519.34207 Da
Source	ChEBI
InChIKey	LHHCSNFAOIFYRV-DOVBMPENSA-N

SMILES

[H][C@@]12[C@@H](C(=O)NC(CC3CCC3)C(=O)C(N)=O)N(C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)C[C@]1([H])C2(C)C

InChI

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

Also called

Victrelis (BRAND_NAME)— chebi
(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 (EXACT_SYNONYM)— chebi
SCH 503034 (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

cas:394730-60-0
pdb-ccd:HU5
reaxys:10502086

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antiviral drug CHEBI:36044

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:68621`	boceprevir	`antibioticmech:chebi-1ea347d2b3`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

hepatitis C virus NS3/4A serine protease VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Protease assays, HCV replicons, and resistance selection associated boceprevir activity with NS3/4A; a compound-bound structure was not used to classify this item as direct binding. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2007-12; 2009-11 (retrieved 2026-09-02).

Organism-specific examples
Protein	Gene	Organism	Entry
Genome polyprotein `UniProtKB:P26662` Reference HCV genotype 1b polyprotein encoding the nonstructural NS3 serine protease and NS4A cofactor inhibited by boceprevir (SCH 503034) in enzyme and replicon assays (PMID:18201776; PMID:20004570; genotype 1b reference isolate BK context).	—	Hepatitis C virus genotype 1b (isolate BK) `NCBITaxon:11108`	REVIEWED

PMID:18201776 (Primary SCH 503034 HCV NS3/4A target and resistance study (DOI:10.1016/j.antiviral.2007.11.010).)
PMID:20004570 (Primary boceprevir-series NS3 protease structure-activity study (DOI:10.1016/j.bmcl.2009.11.094).)

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — CURATOR: PMID:18201776 tested SCH 503034 (boceprevir) against hepatitis C virus NS3/4A protease and selected NS3 resistance substitutions at V36, T54, R155, A156, and V170. PMID:20004570 further measured boceprevir-series inhibition of the NS3 protease. The inspected reports support enzyme inhibition but not a direct-binding classification.
Clinical status: APPROVED

Resistance mechanisms

1 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
HCV NS3 V36, T54, R155, A156, and V170 resistance-associated substitutions Replicon selection and susceptibility testing identified substitutions at these NS3 positions during boceprevir exposure; effects differed by substitution, with A156 substitutions producing the largest losses.	—	not organism-specific	HCV NS3 serine protease	PMID:18201776 (Primary boceprevir resistance-selection and mutant-susceptibility study.)

Record-level evidence

PMID:18201776 (Primary boceprevir target and resistance study.)
PMID:20004570 (Primary boceprevir-series NS3 protease study.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI grounding, recorded structure including its source stereochemical limitation, antiviral class, and FDA assertion; replaced the seeded mechanism note with primary evidence and added the NS3/4A target plus target-alteration resistance.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated HCV genotype 1b isolate BK genome polyprotein (P26662) UniProtKB protein example on the PRIMARY_LITERATURE hepatitis C virus NS3/4A serine protease molecular target.

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

Explore across X-Mech: MediaIngredientMech (boceprevir) · CultureMech · NaturalProductMech · PathwayMech · TraitMech