dolutegravir

CHEBI:76010 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (4R,12aS)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylic acid with the amino group of 2,4-difluorobenzylamine. Used (as its sodium salt) for treatment of HIV-1. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140325
Label unavailable CHEBI:26979
Label unavailable CHEBI:29347
Label unavailable CHEBI:38582

Chemical structure

Computed structure properties
Molecular formula	C20H19F2N3O5
Charge	0
Average mass	419.384 Da
Monoisotopic mass	419.12928 Da
Source	ChEBI
InChIKey	RHWKPHLQXYSBKR-BMIGLBTASA-N

SMILES

[H][C@]12Cn3cc(C(=O)NCc4ccc(F)cc4F)c(=O)c(O)c3C(=O)N1[C@H](C)CCO2

InChI

InChI=1S/C20H19F2N3O5/c1-10-4-5-30-15-9-24-8-13(17(26)18(27)16(24)20(29)25(10)15)19(28)23-7-11-2-3-12(21)6-14(11)22/h2-3,6,8,10,15,27H,4-5,7,9H2,1H3,(H,23,28)/t10-,15+/m1/s1

Also called

(4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide (EXACT_SYNONYM)— chebi
S/GSK1349572 (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.

cas:1051375-16-6
pdb-ccd:DLU
reaxys:12732602

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.

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:76010`	dolutegravir	`antibioticmech:chebi-55508daaf8`	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

Cell-culture integration and purified-integrase biochemical assays compared wild-type with R263K integrase; no compound-bound structure was reported in the inspected abstract. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2011-12 (retrieved 2026-09-02).

PMID:22205735 (Primary selection, reverse-genetics, integration, and purified-enzyme study.)

Mechanism summary

Mode of action: VIRAL_INTEGRASE_INHIBITION microbial target — CURATOR: PMID:22205735 tested dolutegravir against HIV-1 integrase strand-transfer function in virus, site-directed mutant, and purified-enzyme assays. The study also selected and confirmed R263K as a low-level resistance substitution while distinguishing the integration effect from reverse transcription.

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 R263K substitution R263K emerged during in-vitro dolutegravir selection across HIV-1 subtypes and conferred low-level resistance by site-directed mutagenesis while decreasing integration.	—	not organism-specific	HIV-1 integrase	PMID:22205735 (Primary in-vitro selection and site-directed-mutagenesis study.)

Record-level evidence

PMID:22205735 (Primary integrase target and resistance study.)
PMID:22018760 (Primary randomized phase-2b antiviral-activity 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; added the measured HIV-1 integrase target and R263K 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.

Provenance

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

Explore across X-Mech: MediaIngredientMech (dolutegravir) · CultureMech · NaturalProductMech · PathwayMech · TraitMech