narlaprevir

CHEBI:173104 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

An azabicyclohexane that is (1R,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane substituted by [(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]aminoacyl and N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl groups at positions 2S and 3, respectively. It is a hepatitis C virus (HCV) NS3/4A serine protease inhibitor (Ki = 6 nM) that is used for the treatment of chronic hepatitis C. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140325
Label unavailable CHEBI:140326
Label unavailable CHEBI:170008
Label unavailable CHEBI:35850
Label unavailable CHEBI:46770
Label unavailable CHEBI:47857
Label unavailable CHEBI:51454

Chemical structure

Computed structure properties
Molecular formula	C36H61N5O7S
Charge	0
Average mass	707.979 Da
Monoisotopic mass	707.42917 Da
Source	ChEBI
InChIKey	RICZEKWVNZFTNZ-LFGITCQGSA-N

SMILES

[H][C@@]12[C@@H](C(=O)N[C@@H](CCCC)C(=O)C(=O)NC3CC3)N(C(=O)[C@@H](NC(=O)NC3(CS(=O)(=O)C(C)(C)C)CCCCC3)C(C)(C)C)C[C@]1([H])C2(C)C

InChI

InChI=1S/C36H61N5O7S/c1-10-11-15-24(27(42)30(44)37-22-16-17-22)38-29(43)26-25-23(35(25,8)9)20-41(26)31(45)28(33(2,3)4)39-32(46)40-36(18-13-12-14-19-36)21-49(47,48)34(5,6)7/h22-26,28H,10-21H2,1-9H3,(H,37,44)(H,38,43)(H2,39,40,46)/t23-,24-,25-,26-,28+/m0/s1

Also called

Arlansa (BRAND_NAME)— chebi
narlaprevirum (INN)— chebi
narlaprévir (INN)— chebi
(1R,2S,5S)-3-[N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide (EXACT_SYNONYM)— chebi
(1R,2S,5S)-3-{(2S)-2-[({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)amino]-3,3-dimethylbutanoyl}-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide (EXACT_SYNONYM)— chebi
(1R,2S,5S)-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-[3-methyl-N-({1-[(2-methylpropane-2-sulfonyl)methyl]cyclohexyl}carbamoyl)-L-valyl]-3-azabicyclo[3.1.0]hexane-2-carboxamide (EXACT_SYNONYM)— chebi
SCH 900518 (EXACT_SYNONYM)— chebi
SCH-900518 (EXACT_SYNONYM)— chebi
SCH900518 (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:Narlaprevir

Activity roles

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

anticoronaviral agent CHEBI:149553
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:173104`	narlaprevir	`antibioticmech:chebi-0e362fec79`	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

Compound-discovery enzyme-potency and antiviral optimization; the inspected abstract identifies the target but does not establish a direct compound-bound structure. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2010-02 (retrieved 2026-09-02).

Organism-specific examples
Protein	Gene	Organism	Entry
Genome polyprotein `UniProtKB:P26662` Reference HCV genotype 1b polyprotein encoding the NS3/4A serine protease inhibited by narlaprevir (SCH 900518) during discovery and potency optimization (PMID:24900178; genotype 1b reference isolate BK context).	—	Hepatitis C virus genotype 1b (isolate BK) `NCBITaxon:11108`	REVIEWED

PMID:24900178 (Primary medicinal-chemistry discovery and target-potency report.)

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — CURATOR: PMID:24900178 reports the compound-specific discovery and potency optimization of narlaprevir as an HCV NS3 serine-protease inhibitor. PMID:24168257 identified NS3 resistance-associated substitutions during treatment and measured a smaller viral-load decline in participants carrying them.

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, and A156 resistance-associated substitutions Longitudinal clonal sequencing detected substitutions at these NS3 positions during narlaprevir exposure; participants with detected substitutions had a smaller viral-load decline, and R155K persisted in two participants for 3.1 years. Taxon grounding only: the source calls the virus HCV. The clinical association does not establish an individual patient's UniProt accession, strain TaxID or genome. No allele coordinates or resistance measurements were added.	—	Orthohepacivirus hominis `NCBITaxon:3052230`	HCV NS3 serine protease	PMID:24168257 (Primary treatment-exposure, clonal-sequencing, and viral-load study.) https://rest.uniprot.org/taxonomy/3052230 (Taxonomic identity only: active species; Hepatitis C virus is an explicit name alias. Retrieved 2026-10-08 UTC.)

Record-level evidence

PMID:24900178 (Primary narlaprevir discovery and HCV NS3 target study.)
PMID:24168257 (Primary longitudinal clinical viral-sequence 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; replaced the mixed SARS/HCV seed rationale with narlaprevir-specific HCV NS3/4A evidence and added target-alteration resistance observed during treatment.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
GROUNDED_RESISTANCE_TAXON 2026-10-08 · codex · LLM-assisted
Grounded the existing HCV clinical association to an active species TaxID; retained the original claim without assigning patient-specific proteins, strains, genomes or allele coordinates.
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).

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