CHEBI:68606 - rilpivirine

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ChEBI Name rilpivirine
ChEBI ID CHEBI:68606
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H18N6
Net Charge 0
Average Mass 366.41850
Monoisotopic Mass 366.159
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+
InChIKey YIBOMRUWOWDFLG-ONEGZZNKSA-N
SMILES Cc1cc(\C=C\C#N)cc(C)c1Nc1ccnc(Nc2ccc(cc2)C#N)n1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
A DNA polymerase inhibitor that interferes with the activity of reverse transcriptase, EC 2.7.7.49, a viral DNA polymerase enzyme that retroviruses need in order to reproduce.
HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rilpivirine (CHEBI:68606) has role EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor (CHEBI:59897)
rilpivirine (CHEBI:68606) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
rilpivirine (CHEBI:68606) is a aminopyrimidine (CHEBI:38338)
rilpivirine (CHEBI:68606) is a nitrile (CHEBI:18379)
rilpivirine (CHEBI:68606) is conjugate base of rilpivirine(1+) (CHEBI:68605)
Incoming rilpivirine(1+) (CHEBI:68605) is conjugate acid of rilpivirine (CHEBI:68606)
IUPAC Name
4-{[4-({4-[(E)-2-cyanoethenyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
INN Source
rilpivirine KEGG DRUG
Synonyms Sources
4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile IUPAC
TMC 278 ChemIDplus
TMC278 ChemIDplus
Manual Xrefs Databases
D09720 KEGG DRUG
Rilpivirine Wikipedia
T27 PDBeChem
US2008280849 Patent
WO2004016581 Patent
WO2004069812 Patent
WO2006035067 Patent
WO2006035068 Patent
WO2006035069 Patent
WO2007082922 Patent
WO2007113254 Patent
WO2009007441 Patent
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Registry Numbers Types Sources
500287-72-9 CAS Registry Number ChemIDplus
500287-72-9 CAS Registry Number KEGG DRUG
9952270 Reaxys Registry Number Reaxys
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Last Modified
07 April 2016