narlaprevir

CHEBI:173104 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

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

Equivalent identifiers for this same structure in other resources.

cas:865466-24-6
chemspider:10031710
drugbank:DB14760
kegg.drug:D09644
lincs.smallmolecule:LSM-45473
pdb-ccd:NNA
wikipedia.en:Narlaprevir

Activity roles

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

CHEBI:149553 CHEBI:149553
CHEBI:36044 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

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:147285 (EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor), CHEBI:64924 (hepatitis C protease inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

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

Provenance

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