rilpivirine

CHEBI:68606 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

An aminopyrimidine that is pyrimidine-2,4-diamine in which the amino groups at positions 2 and 4 are substituted by 4-cyanophenyl and 4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl groups respectively. Used for treatment of HIV. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:18379
Label unavailable CHEBI:38338

Chemical structure

Computed structure properties
Molecular formula	C22H18N6
Charge	0
Average mass	366.428 Da
Monoisotopic mass	366.15929 Da
Source	ChEBI
InChIKey	YIBOMRUWOWDFLG-ONEGZZNKSA-N

SMILES

Cc1cc(/C=C/C#N)cc(C)c1Nc1ccnc(Nc2ccc(C#N)cc2)n1

InChI

InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+

Also called

4-{[4-({4-[(E)-2-cyanoethenyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile (EXACT_SYNONYM)— chebi
4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile (EXACT_SYNONYM)— chebi
TMC 278 (EXACT_SYNONYM)— chebi
TMC278 (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.

Activity roles

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

HIV-1 reverse transcriptase inhibitor CHEBI:53756
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor CHEBI:59897

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:68606`	rilpivirine	`antibioticmech:chebi-c0a409723f`	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 reverse transcriptase VIRAL_PROTEIN DIRECT_BINDING_TARGET

X-ray crystal structures resolved rilpivirine bound to both wild-type and K103N HIV-1 reverse transcriptase. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2010-05 (retrieved 2026-09-02).

Organism-specific examples
Protein	Gene	Organism	Entry
Gag-Pol polyprotein `UniProtKB:P04585` HIV-1 Gag-Pol precursor encoding the p66/p51 reverse transcriptase heterodimer crystallized in complex with rilpivirine (TMC278) in wild-type and K103N mutant forms (PMID:20438081, PDB 2ZD1 / 3MEE; HXB2 reference isolate context).	gag-pol	Human immunodeficiency virus type 1 group M subtype B (isolate HXB2) `NCBITaxon:11706`	REVIEWED

PMID:20438081 (Primary compound-enzyme crystal-structure study.)

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — CURATOR: PMID:20438081 determined crystal structures of rilpivirine bound to wild-type and K103N HIV-1 reverse transcriptase, directly confirming the non-nucleoside viral polymerase target and showing a similar binding mode in both enzyme forms.

Record-level evidence

PMID:20438081 (Primary wild-type and K103N reverse-transcriptase structural 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, antiviral class, and role; curator-confirmed viral polymerase inhibition and added the directly observed HIV-1 reverse-transcriptase binding target.
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.
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated HIV-1 HXB2 Gag-Pol polyprotein (P04585) UniProtKB protein example on the PRIMARY_LITERATURE HIV-1 reverse transcriptase molecular target.

Provenance

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

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