AntibioticMech

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dasabuvir

CHEBI:85182 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A member of the class of pyrimidone, which is (as the monohydrate of its sodium salt) in combination with ombitasvir, paritaprevir and ritonavir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC26H27N3O5S
Charge0
Average mass493.585 Da
Monoisotopic mass493.16714 Da
SourceChEBI
InChIKeyNBRBXGKOEOGLOI-UHFFFAOYSA-N

SMILES

COc1c(-c2ccc3cc(NS(C)(=O)=O)ccc3c2)cc(-n2ccc(=O)nc2=O)cc1C(C)(C)C

InChI

InChI=1S/C26H27N3O5S/c1-26(2,3)22-15-20(29-11-10-23(30)27-25(29)31)14-21(24(22)34-4)18-7-6-17-13-19(28-35(5,32)33)9-8-16(17)12-18/h6-15,28H,1-5H3,(H,27,30,31)

Also called

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.

Activity roles

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

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
SourceNative IDLabelMinted CURIEVersion
CHEBI CHEBI:85182 dasabuvir antibioticmech:chebi-1e05e8c607 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 NS5B RNA-dependent RNA polymerase palm-I site VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Recombinant genotype 1a and 1b NS5B inhibition and subgenomic replicon assays; selected substitutions were consistent with the palm-I site, but the abstract did not report a direct compound-bound structure. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2014-12 (retrieved 2026-09-02).

Mechanism summary

Mode of action
VIRAL_POLYMERASE_INHIBITION microbial target — CURATOR: PMID:25534735 measured nanomolar inhibition of recombinant hepatitis C virus genotype 1a and 1b NS5B RNA-dependent RNA polymerases and genotype-matched replicons. Resistant NS5B variants selected in vitro were consistent with binding at the polymerase palm-I site; the record therefore uses measured target association rather than an unqualified direct-binding claim.

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
DeterminantARO IDOrganismGene familiesEvidence
HCV NS5B C316Y, M414T, Y448C/Y448H, and S556G variants
These NS5B variants were selected in genotype 1 replicon cells maintained at 10- or 100-fold the dasabuvir EC50 and were consistent with interaction at the polymerase palm-I site. Compound-form review pending: PMID:25534735 names a sodium form in its Compound section, whereas this record is neutral dasabuvir. This existing claim has not been revalidated for exact-form placement; no additional organism, protein or allele grounding is assigned pending resolution.		 — not organism-specific HCV NS5B RNA-dependent RNA polymerase
  • PMID:25534735 (Primary in-vitro selection and sequencing study.)

Discussions

Open questions, knowledge gaps and curation todos attached to this compound.

CURATION_TODO OPEN

Resolve the placement of PMID:25534735 evidence on neutral dasabuvir: the paper's Compound section names a sodium form. Does the evidence belong on a different structure record or require an explicit active-moiety interpretation?

Neutral dasabuvir (CHEBI:85182), dasabuvir sodium (CHEBI:85179), and dasabuvir sodium hydrate (CHEBI:85178) have distinct InChIKeys. The inspected text does not establish hydration state or justify copying this study to all three records.

Attached to: chemical_structure, resistance_mechanisms, molecular_targets, mode_of_action

Record-level evidence

Curation history

  1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Seeded from data/raw/ inventories (CHEBI)

  2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  4. REVIEWED 2026-09-02 · codex · LLM-assisted

    Verified exact ChEBI identity, structure, and antiviral class; added the primary-evidence NS5B polymerase mechanism, measured palm-I target association, and selected target-alteration resistance variants.

  5. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

    Re-seeded from updated data/raw/ inventories

  6. FLAGGED_COMPOUND_FORM_REVIEW 2026-10-08 · codex · LLM-assisted

    Flagged primary-paper material-form ambiguity in an open discussion and the existing resistance note. Preserved chemical identity, claim evidence and prior review status; did not transfer or expand the claim.

Provenance

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

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