etravirine

CHEBI:63589 ·resolve ·ANTIVIRAL ·EXACT SEEDED

An aminopyrimidine that consists of 2,6-diaminopyrimidine bearing a bromo substituent at position 5, a 4-cyano-2,6-dimethylphenoxy substituent at position 4 and having a 4-cyanophenyl substituent attached to the 2-amino group. NNRTI of HIV-1, binds directly to RT and blocks RNA-dependent and DNA-dependent DNA polymerase activities — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:35618
Label unavailable CHEBI:37141
Label unavailable CHEBI:38338
Label unavailable CHEBI:51308

Chemical structure

Computed structure properties
Molecular formula	C20H15BrN6O
Charge	0
Average mass	435.285 Da
Monoisotopic mass	434.04907 Da
Source	ChEBI
InChIKey	PYGWGZALEOIKDF-UHFFFAOYSA-N

SMILES

Cc1cc(C#N)cc(C)c1Oc1nc(Nc2ccc(C#N)cc2)nc(N)c1Br

InChI

InChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)

Also called

4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile (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:269055-15-4
reaxys:8945855

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:Etravirine

Activity roles

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

antiviral agent CHEBI:22587
HIV-1 reverse transcriptase inhibitor CHEBI:53756

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:63589`	etravirine	`antibioticmech:chebi-dfa595f854`	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.

Reverse transcriptase protein VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Human immunodeficiency virus 1 NCBITaxon:11676

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	89 nM	In vitro Anti-HIV RT Assay The HIV-1 RTwt inhibition assay was implemented using the template/primer hybrid poly(A)9oligo(dT)15, digoxigenin- and biotin-labeled nucleotides, an antibody to digoxigenin which is conjugated to peroxidase (anti-DIG-POD), and the peroxidase substrate ABTS for quantifying the RT polymerase activity. The incorporation quantities of the digoxigenin- and biotin-labeled dUTP into DNA represented the activity of HIV-1 RT. The IC50 value corresponds to the concentration of the tested compound required to inhibit the incorporation of the labeled dUTP by 50%. The procedure for RT assay was performed as described in the kit (Roche) protocol	`RSID 306800` `assay 6988_1` `monomer 50103642`	`PMID:25511999`

Organism-specific examples
Protein	Gene	Organism	Entry
Reverse transcriptase protein `UniProtKB:Q9WJQ1` BindingDB target chain 1	—	Human immunodeficiency virus 1 `NCBITaxon:11676`	UNREVIEWED

PMID:25511999 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.
Clinical status: APPROVED

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
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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).

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