Narlaprevir

Summary

Narlaprevir (CHEMBL1255891) is a phase-3 clinical-stage small-molecule hepatitis C protease inhibitor (ATC J05AP14); indicated across 4 conditions including hepatitis c virus infection and viral infectious disease.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• ATC class: J05AP14
• Indications: 4 conditions
• Clinical trials: 7
• Chemistry: 708 Da · C36H61N5O7S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1255891
Name	Narlaprevir
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	11857239
ChEBI	CHEBI:173104
ATC	J05AP14
Molecular formula	C36H61N5O7S
Molecular weight	708
InChIKey	RICZEKWVNZFTNZ-LFGITCQGSA-N

SMILES: CCCC[C@@H](C(=O)C(=O)NC1CC1)NC(=O)[C@@H]2[C@@H]3[C@@H](C3(C)C)CN2C(=O)[C@H](C(C)(C)C)NC(=O)NC4(CCCCC4)CS(=O)(=O)C(C)(C)C

IUPAC name: (1R,2S,5S)-3-[(2S)-2-[[1-(tert-butylsulfonylmethyl)cyclohexyl]carbamoylamino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

ChEBI definition: 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.

Pharmacological roles (ChEBI): hepatitis C protease inhibitor, antiviral drug, EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, anticoronaviral agent.

Also known as: Narlaprevir, SCH 900518, SCH-900518, narlaprevir, NARLAPREVIR

Patent coverage: 184 distinct patent families (437 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Replicase polyprotein 1ab.

Bioactivity

ChEMBL activities: 4 potent at pChembl ≥ 5 of 4 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P0DTD1	5.66	IC50	2200	nM	CHEMBL_ACT_25952145
P0DTD1	5.24	IC50	5730	nM	CHEMBL_ACT_24660843
P0DTD1	5.24	IC50	5728	nM	CHEMBL_ACT_24660871
P0DTD1	5.24	IC50	5700	nM	CHEMBL_ACT_25930829

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

4 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
hepatitis C virus infection	3	MONDO:0005231	EFO:0003047
viral infectious disease	3	MONDO:0005108	EFO:0000763
chronic hepatitis C virus infection	2	MONDO:0005354	EFO:0004220
liver disorder	1	MONDO:0005154	EFO:0001421

Clinical trials

Total trials: 7.

Phase distribution

Phase	Trials
PHASE2	3
PHASE1	2
PHASE2/PHASE3	1
PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00689390	PHASE2/PHASE3	TERMINATED	Three-year Follow-up of Participants After Administration of Boceprevir or Narlaprevir for the Treatment of Chronic Hepatitis C (P05063)
NCT03833362	PHASE3	COMPLETED	Efficacy and Safety of Narlaprevir Used in Combination With Ritonavir in Treatment-Naïve and Failed Prior Treatment With Pegylated Interferon/Ribavirin Patients With Chronic Hepatitis C Genotype 1 (PIONEER - Study)
NCT00797745	PHASE2	COMPLETED	A Pharmacokinetics/Pharmacodynamics Study of SCH 900518 in Previously Untreated Subjects With Genotype 1 Chronic Hepatitis C (Protocol No. P05104AM2)(COMPLETED)
NCT03485846	PHASE2	COMPLETED	Efficacy and Safety of All-Oral Combination of Narlaprevir/Ritonavir and Daclatasvir in Treatment-Naїve Patients With Chronic Hepatitis C Genotype 1b
NCT04246723	PHASE2	COMPLETED	Efficacy and Safety of All-Oral Combination of Narlaprevir/Ritonavir and Sofosbuvir in Treatment-naïve Patients With Chronic Hepatitis C Genotype 1
NCT03537404	PHASE1	COMPLETED	A Drug Interaction Study to Assess the Pharmacokinetics of Narlaprevir and Antiretroviral Drugs
NCT03832426	PHASE1	COMPLETED	A Pharmacokinetic Study of Narlaprevir as a Single Dose or With Ritonavir Combination in Patients With Hepatic Impairment and Healthy Matched Volunteers

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).