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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 of Rilpivirine

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
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

Curator's Comment: Common side effects may include Central Nervous System (CNS) related side effects including dizziness, difficulty with concentration, sleep disturbances, vivid dreams, agitation, nausea (upset stomach, feeling sick to the stomach), dizziness, sleep disturbances.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
14.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.14 μg/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2.38 μg × h/mL
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.3%
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
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

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
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
  • Download
Name Type Language
Rilpivirine
DASH   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
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
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
WHO-ATC J05AR08
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
FDA ORPHAN DRUG 858321
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
NDF-RT N0000175463
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
NCI_THESAURUS C97453
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
WHO-VATC QJ05AG05
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
WHO-ATC J05AR19
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
LIVERTOX NBK548514
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
WHO-ATC J05AR21
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
WHO-VATC QJ05AR08
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
Code System Code Type Description
CHEBI
68602
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
NCI_THESAURUS
C76929
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
INN
8469
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
PUBCHEM
6451164
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
CAS
500287-72-9
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
DRUG BANK
DB08864
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
HSDB
8153
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
MERCK INDEX
m9619
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY Merck Index
USAN
WW-86
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
EVMPD
SUB31456
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
SMS_ID
100000124141
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
RXCUI
1102270
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID10198189
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
DAILYMED
FI96A8X663
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
WIKIPEDIA
RILPIVIRINE
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
LACTMED
Rilpivirine
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
CHEBI
68606
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
ChEMBL
CHEMBL175691
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
DRUG CENTRAL
4174
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
FDA UNII
FI96A8X663
Created by admin on Mon Mar 31 18:26:13 GMT 2025 , Edited by admin on Mon Mar 31 18:26:13 GMT 2025
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
FECAL
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET ORGANISM->INHIBITOR
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Blood-to-plasma ratio PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC oral administration