raltegravir

CHEBI:82960 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A pyrimidone that is pyrimidin-4(3H)-one in which the hydrogens at positions 2, 3, 5 and 6 are replaced by 2-[(5-methyl-1,3,4-oxadiazole-2-carbonyl)amino]propan-2-yl, methyl, hydroxy, and N-[(4-fluorophenyl)methyl]aminoacyl groups, respectively. It is an antiretroviral drug used for treatment of HIV infection. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:140325
Label unavailable CHEBI:23690
Label unavailable CHEBI:38337
Label unavailable CHEBI:38340
Label unavailable CHEBI:46809
Label unavailable CHEBI:83575

Chemical structure

Computed structure properties
Molecular formula	C20H21FN6O5
Charge	0
Average mass	444.423 Da
Monoisotopic mass	444.15575 Da
Source	ChEBI
InChIKey	CZFFBEXEKNGXKS-UHFFFAOYSA-N

SMILES

Cc1nnc(C(=O)NC(C)(C)c2nc(C(=O)NCc3ccc(F)cc3)c(O)c(=O)n2C)o1

InChI

InChI=1S/C20H21FN6O5/c1-10-25-26-17(32-10)16(30)24-20(2,3)19-23-13(14(28)18(31)27(19)4)15(29)22-9-11-5-7-12(21)8-6-11/h5-8,28H,9H2,1-4H3,(H,22,29)(H,24,30)

Also called

raltegravirum (INN)— chebi
raltégravir (INN)— chebi
N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-(2-{[(5-methyl-1,3,4-oxadiazol-2-yl)carbonyl]amino}propan-2-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxamide (EXACT_SYNONYM)— chebi
MK 0518 (EXACT_SYNONYM)— chebi
MK-0518 (EXACT_SYNONYM)— chebi
MK0518 (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:Raltegravir

Activity roles

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

antiviral drug CHEBI:36044
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:82960`	raltegravir	`antibioticmech:chebi-f7341e2eb0`	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.

retroviral integrase-DNA intasome active site VIRAL_PROTEIN DIRECT_BINDING_TARGET

Raltegravir-bound prototype foamy virus intasome cocrystal structures defined the conserved strand-transfer-inhibitor binding mode; this is a retroviral structural model rather than an HIV-1 intasome structure. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2010-10 (retrieved 2026-09-02).

PMID:21030679 (Primary inhibitor-intasome structural and resistance-mechanism study.)

Mechanism summary

Mode of action: VIRAL_INTEGRASE_INHIBITION microbial target — CURATOR: PMID:21030679 reports raltegravir-bound retroviral intasome cocrystal structures that establish the integrase strand-transfer inhibitor binding mode and explain resistance-associated active-site rearrangements. The structural model uses prototype foamy virus integrase, with HIV-1 resistance positions mapped to homologous sites.

Resistance mechanisms

2 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
PFV integrase N224H biochemical raltegravir resistance model PFV model; HIV-1 N155H is comparative context, not this allele. P14350 is the reference Pro-Pol polyprotein containing integrase, not a mutant-specific accession. Source integrase numbering retained without conversion to polyprotein coordinates. No whole-virus phenotype, clinical resistance call, strain TaxID or genome inferred.	—	Human spumaretrovirus `NCBITaxon:11963` `UniProtKB:P14350`	retroviral integrase	PMID:21030679 (Results and Discussion; Figure 3. PFV biochemical model.) UniProtKB:P14350 (Reference identity via PDB:3OYM; sequence version 2, release 2026_03.) https://rest.uniprot.org/taxonomy/11963 (Active identifier, rank no rank, not a species-level assignment. Retrieved 2026-10-08 UTC.) Biochemical integrase inhibition assay
PFV integrase S217H biochemical raltegravir resistance model PFV model; HIV-1 Q148H/G140S is comparative context, not this allele. P14350 is the reference Pro-Pol polyprotein containing integrase, not a mutant-specific accession. Source integrase numbering retained without conversion to polyprotein coordinates. No whole-virus phenotype, clinical resistance call, strain TaxID or genome inferred.	—	Human spumaretrovirus `NCBITaxon:11963` `UniProtKB:P14350`	retroviral integrase	PMID:21030679 (Results and Discussion; Figure 3. PFV biochemical model.) UniProtKB:P14350 (Reference identity via PDB:3OYK; sequence version 2, release 2026_03.) https://rest.uniprot.org/taxonomy/11963 (Active identifier, rank no rank, not a species-level assignment. Retrieved 2026-10-08 UTC.) Biochemical integrase inhibition assay

Record-level evidence

PMID:21030679 (Primary raltegravir-bound intasome structural study.)
PMID:17133211 (Primary short-course randomized clinical antiviral-activity study of MK-0518.)

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 direct retroviral intasome target, explicit prototype-foamy-virus model limitation, and structurally supported resistance pathways.
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_MODEL 2026-10-08 · codex · LLM-assisted
Separated the existing PFV biochemical-model observations; grounded reference protein and taxonomy without assigning the model to HIV-1 subjects. Preserved all HIVDB score rules.

Provenance

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

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