bictegravir

CHEBI:172943 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2R,5S,13aR)-8-hydroxy-7,9-dioxo-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxylic acid with the amino group of 2,4,6-trifluorobenzylamine. It is a second-generation integrase strand transfer inhibitor (INSTI) and used (as its sodium salt) for the treatment of HIV-1. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140325
Label unavailable CHEBI:29347
Label unavailable CHEBI:38163
Label unavailable CHEBI:83576

Chemical structure

Computed structure properties
Molecular formula	C21H18F3N3O5
Charge	0
Average mass	449.385 Da
Monoisotopic mass	449.11986 Da
Source	ChEBI
InChIKey	SOLUWJRYJLAZCX-LYOVBCGYSA-N

SMILES

[H][C@@]12CC[C@@]([H])(C1)N1C(=O)c3c(O)c(=O)c(C(=O)NCc4c(F)cc(F)cc4F)cn3C[C@@]1([H])O2

InChI

InChI=1S/C21H18F3N3O5/c22-9-3-14(23)12(15(24)4-9)6-25-20(30)13-7-26-8-16-27(10-1-2-11(5-10)32-16)21(31)17(26)19(29)18(13)28/h3-4,7,10-11,16,29H,1-2,5-6,8H2,(H,25,30)/t10-,11+,16+/m0/s1

Also called

bictegravirum (INN)— chebi
bictégravir (INN)— chebi
(2R,5S,13aR)-8-hydroxy-7,9-dioxo-N-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide (EXACT_SYNONYM)— chebi
GS-9883 (EXACT_SYNONYM)— chebi
GS-9883-01 (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:Bictegravir

Activity roles

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

HIV-1 integrase inhibitor CHEBI:67268

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:172943`	bictegravir	`antibioticmech:chebi-39ab9e78dd`	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.

HIV-1 integrase strand-transfer activity VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Biochemical strand-transfer inhibition and cellular HIV-1 integration assays; the abstract reports an IC50 of 7.5 +/- 0.3 nM for strand-transfer activity. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2016-11 (retrieved 2026-09-02).

PMID:27645238 (Primary compound-specific biochemical, cellular, activity, and resistance-profile study.)

Mechanism summary

Mode of action: VIRAL_INTEGRASE_INHIBITION microbial target — CURATOR: PMID:27645238 measured inhibition of HIV-1 integrase strand transfer (IC50 7.5 +/- 0.3 nM), inhibition of viral integration in cells, and nanomolar antiviral activity. This establishes a target-associated integrase mechanism but is not represented as a direct physical-binding measurement.

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
HIV-1 integrase M50I/R263K substitutions The dual integrase substitutions were selected during in-vitro dose escalation and produced 2.8-fold reduced bictegravir susceptibility relative to wild-type virus. Species-grounding update (2026-10-14): the existing laboratory HIV-1 claim is placed in Lentivirus humimdef1 (NCBITaxon:3418650). The cited paper's Results distinguish selected viral populations, site-directed test viruses and patient-derived isolates; these are not interchangeable experimental subjects. This species-only update does not independently revalidate the inherited variant or quantitative statement, establish the tested compound's exact formulation, or assign a protein accession, strain TaxID, experimental genome, patient identity or normalized allele. UniProt's HIV-1 name node NCBITaxon:11676 is unranked beneath this species.	—	Lentivirus humimdef1 `NCBITaxon:3418650`	HIV-1 integrase	PMID:27645238 (Primary in-vitro selection and phenotypic-susceptibility study.) https://rest.uniprot.org/taxonomy/3418650 (Species context only: native UniProt Taxonomy release 2026_03 responses for 11676 (retrieved 2026-10-08) and 3418650 (retrieved 2026-10-14) place the active HIV-1 name node under active species Lentivirus humimdef1. Cached responses were reused, not newly queried. PMID:27645238 Results identify HIV-1 in the laboratory comparison behind the existing claim. Taxonomy does not identify the tested derivative or establish an experimental protein, allele or genome.)

Record-level evidence

PMID:27645238 (Primary mechanism, antiviral-activity, and in-vitro resistance-profile 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; curator-confirmed HIV-1 integrase strand-transfer inhibition and added the measured target association and selected target-alteration resistance with primary evidence.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-28 · seed_from_sources
Re-seeded; changed: genotype_resistance_score_rules (HIVDB_HIVFACTS be1c11a5145fea9073fdb71801919d4a34265336). Upstream retrieval date 2026-08-30, unchanged.
GROUNDED_RESISTANCE_TAXONOMY 2026-10-14 · codex · LLM-assisted
Grounded the existing bictegravir laboratory HIV-1 resistance claim at species rank as Lentivirus humimdef1 (NCBITaxon:3418650), using PMID:27645238 primary Results organism context and cached UniProt taxonomy release 2026_03. Preserved inherited claim wording, mechanism, gene-family label, quantitative statement and citation. Distinguished selected populations, test viruses and patient-derived isolates without assigning an experimental protein, strain, allele or genome. No new variants or numeric AST were added; exact formulation and whole-record primary review remain open.

Provenance

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

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