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.

CHEBI:35618 CHEBI:35618
CHEBI:37141 CHEBI:37141
CHEBI:38338 CHEBI:38338
CHEBI:51308 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

Equivalent identifiers for this same structure in other resources.

cas:269055-15-4
drugbank:DB06414
kegg.drug:D04112
reaxys:8945855
wikipedia.en:Etravirine

Activity roles

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

CHEBI:22587 CHEBI:22587
CHEBI:53756 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`	—	Human immunodeficiency virus 1	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

Provenance

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