vaniprevir

CHEBI:136047 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

An azamacrocyclic compound that is a hepatitis C virus (HCV) NS3/4A protease inhibitor which is approved for the treatment of hepatitis C virus infections in Japan. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:23003
Label unavailable CHEBI:46770
Label unavailable CHEBI:51454
Label unavailable CHEBI:52898
Label unavailable CHEBI:90852

Chemical structure

Computed structure properties
Molecular formula	C38H55N5O9S
Charge	0
Average mass	757.951 Da
Monoisotopic mass	757.37205 Da
Source	ChEBI
InChIKey	KUQWGLQLLVFLSM-ONAXAZCASA-N

SMILES

[H][C@@]12CN(C(=O)[C@]([H])(C(C)(C)C)NC(=O)OCC(C)(C)CCCCc3cccc4c3CN(C4)C(=O)O1)[C@]([H])(C(=O)N[C@]1(C(=O)NS(=O)(=O)C3CC3)C[C@@]1([H])CC)C2

InChI

InChI=1S/C38H55N5O9S/c1-7-25-18-38(25,33(46)41-53(49,50)27-14-15-27)40-31(44)29-17-26-20-43(29)32(45)30(36(2,3)4)39-34(47)51-22-37(5,6)16-9-8-11-23-12-10-13-24-19-42(21-28(23)24)35(48)52-26/h10,12-13,25-27,29-30H,7-9,11,14-22H2,1-6H3,(H,39,47)(H,40,44)(H,41,46)/t25-,26-,29+,30-,38-/m1/s1

Also called

Vanihep (BRAND_NAME)— chebi
vaniprevirum (INN)— chebi
vaniprévir (INN)— chebi
(5R,7S,10S)-10-tert-butyl-N-{(1R,2R)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethylcyclopropyl}-15,15-dimethyl-3,9,12-trioxo-6,7,9,10,11,12,14,15,16,17,18,19-dodecahydro-1H,5H-2,23:5,8-dimethano-4,13,2,8,11-benzodioxatriazacyclohenicosine-7(3H)-carboxamide (EXACT_SYNONYM)— chebi
MK 7009 (EXACT_SYNONYM)— chebi
MK-7009 (EXACT_SYNONYM)— chebi
MK7009 (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.

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.

wikipedia.en:Vaniprevir

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:136047`	vaniprevir	`antibioticmech:chebi-0fbb86a23c`	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 protease VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Purified genotype 1a, 1b, 2a, and 2b protease inhibition and cell-based HCV replicon assays; no compound-bound structure was reported in the inspected abstract. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2009-10 (retrieved 2026-09-02).

Organism-specific examples
Protein	Gene	Organism	Entry
Genome polyprotein `UniProtKB:P26664` Reference HCV genotype 1a polyprotein encoding the NS3/4A protease inhibited at subnanomolar potency by vaniprevir (MK-7009) (PMID:19841155; genotype 1a reference isolate H context).	—	Hepatitis C virus genotype 1a (isolate H) `NCBITaxon:63746`	REVIEWED
Genome polyprotein `UniProtKB:P26662` Reference HCV genotype 1b polyprotein encoding the NS3/4A protease inhibited at subnanomolar potency by vaniprevir (MK-7009) (PMID:19841155; genotype 1b reference isolate BK context).	—	Hepatitis C virus genotype 1b (isolate BK) `NCBITaxon:11108`	REVIEWED

PMID:19841155 (Primary compound-specific enzyme, replicon, and selectivity study.)

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — CURATOR: PMID:19841155 measured subnanomolar inhibition of HCV genotype 1a and 1b NS3/4A proteases by MK-7009 (vaniprevir), plus potent HCV replicon activity and selectivity against human proteases. PMID:23747481 confirmed antiviral activity in people with genotype 1 infection and identified resistance-associated NS3 variants.

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 R155 and D168 resistance-associated variants Variants at NS3 positions R155 and D168 were identified after eight days of vaniprevir monotherapy in participants with HCV genotype 1a infection.	—	not organism-specific	HCV NS3/4A protease	PMID:23747481 (Primary randomized dose-ranging monotherapy study.)

Record-level evidence

PMID:19841155 (Primary preclinical target and activity study.)
PMID:23747481 (Primary short-course clinical antiviral and resistance 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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, and antiviral class; added compound-specific HCV NS3/4A inhibition, the measured viral target, and treatment-emergent target-alteration resistance evidence.
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 1a isolate H (P26664) and genotype 1b isolate BK (P26662) genome polyprotein UniProtKB protein examples on the PRIMARY_LITERATURE hepatitis C virus NS3/4A protease molecular target.

Provenance

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

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