rilpivirine (CHEBI:68606)

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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

Average Mass

366.41850

Monoisotopic Mass

366.15929

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.

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

Last Modified

17 September 2021