AntibioticMech

rilpivirine

CHEBI:68606 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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.

• CHEBI:18379 CHEBI:18379
• CHEBI:38338 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

Equivalent identifiers for this same structure in other resources.

• cas:500287-72-9
• drugbank:DB08864
• hmdb:HMDB0061725
• kegg.drug:D09720
• patent:US2008280849
• patent:WO2004016581
• patent:WO2004069812
• patent:WO2006035067
• patent:WO2006035068
• patent:WO2006035069
• patent:WO2007082922
• patent:WO2007113254
• patent:WO2009007441
• pdb-ccd:T27
• reaxys:9952270
• wikipedia.en:Rilpivirine

Activity roles

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

• CHEBI:53756 CHEBI:53756
• CHEBI:59897 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

Mechanism summary

Mode of action

VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor), CHEBI:59897 (EC 2.7.7.49 (RNA-directed DNA polymerase) 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.

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · 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.