Antimicrobial & Antiviral

Boceprevir

Boceprevir jammed the molecular scissors hepatitis C uses to cut its own polyprotein into working parts, and when the US Food and Drug Administration approved it in 2011 it was a real advance: added to interferon-based treatment it lifted cure rates from about 40% to about 67% in previously untreated patients, at the cost of anaemia in roughly half of them. Four years later it was gone. Not because it stopped working, but because interferon-free regimens arrived and made the trade-off pointless — the manufacturer stopped US distribution in 2015, and the European licence was withdrawn at its holder's request in 2018. It is a peptide-shaped small molecule, held in this corpus for reference.

Last updated 12 August 2026

Studied forHepatitis C research · Viral protease inhibition · Sustained virological response context

Evidence on fileFDA-approved · 2 randomised human trials

Strongest sourceBoceprevir for Untreated Chronic HCV Genotype 1 Infection (New England Journal of Medicine 2011, cited 2030x) (randomised human trial)

Mechanism

Binds the NS3/4A protease active-site serine covalently but reversibly, blocking polyprotein cleavage and viral replication.

Regulatory status

Approved by the FDA. Marketed as VICTRELIS. Earliest approval 2011-05-13. Application NDA202258.

An approval grades as rung 1 on this site, because 21 CFR 314.126 requires adequate and well-controlled human investigations and one cannot be granted without them. It covers specific indications and doses, though, and does not transfer to other uses of the same molecule.

Reported effects

What sources associate with this compound. Reported categories, not outcomes we have graded — each would need its own citation and rung.

Hepatitis C research
Viral protease inhibition
Sustained virological response context

Dosing on file unverified

800 mg (four 200 mg capsules) orally 3x/day (every 7-9h) with food

Carried from a source that labels it unverified, and reproduced with that label attached. A record of what is reported, not a recommendation. No citation on this page establishes it.

Literature on file 3

human RCT
Boceprevir for Untreated Chronic HCV Genotype 1 Infection (New England Journal of Medicine 2011, cited 2030x) graded on: names a randomised controlled trial — the indexed publication type — “Randomized Controlled”
human RCT
Boceprevir for Previously Treated Chronic HCV Genotype 1 Infection (New England Journal of Medicine 2011, cited 1319x) graded on: names a randomised controlled trial — the indexed publication type — “Randomized Controlled”
human RCT
FDA approval NDA202258 graded on: an FDA approval (NDA202258), which requires adequate and well-controlled human investigations — “NDA202258”

Identity

Space-filling 3D model of Boceprevir, carbon grey, nitrogen blue, oxygen red — Built from the SMILES on this record — the atoms and bonds are exact. The shape is **one computed low-energy pose**, not a measured structure: a flexible peptide in solution has no single conformation, and where the SMILES leaves a stereocentre undefined the pose commits to one arbitrarily. The skeletal formula below claims connectivity and nothing more, which is what we actually know.

2D chemical structure of Boceprevir — Built from the SMILES on this record — the atoms and bonds are exact. The shape is **one computed low-energy pose**, not a measured structure: a flexible peptide in solution has no single conformation, and where the SMILES leaves a stereocentre undefined the pose commits to one arbitrarily. The skeletal formula below claims connectivity and nothing more, which is what we actually know.

Molecular weight: 519.7
Molecular formula: C27H45N5O5
CAS number: 394730-60-0
PubChem CID: 10324367
InChI key: LHHCSNFAOIFYRV-DOVBMPENSA-N
SMILES: CC1([C@@H]2[C@H]1[C@H](N(C2)C(=O)[C@H](C(C)(C)C)NC(=O)NC(C)(C)C)C(=O)NC(CC3CCC3)C(=O)C(=O)N)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

Notes unverified prose

FDA-approved (Victrelis) 2011; HCV protease inhibitor – peptide-based, included for reference; FDA-approved (Victrelis) – peptide-based

Not on file 2

1 of the 8 fields we track hold nothing on this record, and each says why. 1 further absence is named below. A blank field is a bug; a named absence is a finding.

amino-acid sequencenot applicable to this compound
half-lifenothing we hold supplies it

Each field links to every other record missing the same thing. The full ledger holds 765 gaps across 163 records.