Rilpivirine

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H18N6
Molecular Weight	366.4185
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(\C=C\C#N)=CC(C)=C1NC2=NC(NC3=CC=C(C=C3)C#N)=NC=C2

InChI

InChIKey=YIBOMRUWOWDFLG-ONEGZZNKSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C22H18N6
Molecular Weight	366.4185
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202022s008lbledt.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/?term=19933797

Rilpivirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) which is used for the treatment of HIV-1 infections in treatment-naive patients. It is active against wild-type and NNRTI-resistant HIV-1. Rilpivirine is a diarylpyrimidinethat inhibits HIV-1 replication by non-competitive inhibition of HIV-1 reverse transcriptase (RT). Rilpivirine does not inhibit the human cellular DNA polymerases α, β and γ.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Reverse transcriptase/RNaseH (UniProtKB: Q72547) 2 Target ID: Reverse transcriptase/RNaseH (UniProtKB: Q72547) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202022s008lbledt.pdf	Inhibitor 8504		14.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202022s008lbledt.pdf	Primary		Approved 8583	EDURANT Approved Use In combination with other antiretroviral agents, is indicated for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in antiretroviral treatment-naïve patients with HIV-1 RNA less than or equal to 100,000 copies/mL at the start of therapy. Launch Date 2011

C_max

Value	Dose	Co-administered	Analyte	Population
0.14 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27187753/	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		RILPIVIRINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED
121 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29335895/	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		RILPIVIRINE plasma	Homo sapiens population: PREGNANT age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2.38 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27187753/	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		RILPIVIRINE plasma	Homo sapiens population: UNHEALTHY age: ADOLESCENT sex: FEMALE / MALE food status: FED
1792 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29335895/	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		RILPIVIRINE plasma	Homo sapiens population: PREGNANT age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29335895/	25 mg 1 times / day multiple, oral dose: 25 mg route of administration: Oral experiment type: MULTIPLE co-administered:		RILPIVIRINE plasma	Homo sapiens population: PREGNANT age: ADULT sex: FEMALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:68606	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68606
ChemicalBook	CB81454833	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB81454833
eMolecules	10663308	https://www.emolecules.com/cgi-bin/more?vid=10663308
MolPort	MolPort-006-170-051	https://www.molport.com/shop/molecule-link/MolPort-006-170-051
ZINC	ZINC000001554274	http://zinc15.docking.org/substances/ZINC000001554274

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

25 mg (one 25 mg tablet) taken once daily with a meal, is not recommended for patients less than 12 years of age. With rifabutin co-administration, the Edurant dose should be increased to 50 mg (two tablets of 25 mg each) taken once daily with a meal.

Route of Administration: Oral

In Vitro Use Guide

TMC278 (rilpivirine) showed subnanomolar 50% effective concentrations (EC50 values) against wild-type HIV-1 group M isolates (0.07 to 1.01 nM) and nanomolar EC50 values against group O isolates (2.88 to 8.45 nM).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:26:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:26:13 GMT 2025`
Record UNII	FI96A8X663
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Rilpivirine

Official Name

English

CABENUVA COMPONENT RILPIVIRINE

Preferred Name

English

Rilpivirine [WHO-DD]

Common Name

English

R278474

Code

English

rilpivirine [INN]

Common Name

English

R-278474

Code

English

TMC-278

Code

English

4-{[4-({4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile

Systematic Name

English

RILPIVIRINE [USAN]

Common Name

English

RILPIVIRINE [MI]

Common Name

English

BENZONITRILE, 4-((4-((4-((1E)-2-CYANOETHENYL)-2,6-DIMETHYLPHENYL)AMINO)-2- PYRIMIDINYL)AMINO)-

Systematic Name

English

RILPIVIRINE [VANDF]

Common Name

English

RILPIVIRINE [MART.]

Common Name

English

RILPIVIRINE [JAN]

Common Name

English

TMC278

Code

English

RILPIVIRINE [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J05AG05