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Details

Stereochemistry ACHIRAL
Molecular Formula C22H18N6.ClH
Molecular Weight 402.879
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Rilpivirine Hydrochloride

SMILES

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

InChI

InChIKey=KZVVGZKAVZUACK-BJILWQEISA-N
InChI=1S/C22H18N6.ClH/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);1H/b4-3+;

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 18:52:09 GMT 2025
Edited
by admin
on Mon Mar 31 18:52:09 GMT 2025
Record UNII
212WAX8KDD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EDURANT
Preferred Name English
Rilpivirine Hydrochloride
MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
RILPIVIRINE HCL
Common Name English
BENZONITRILE, 4-((4-((4-((1E)-2-CYANOETHENYL)-2,6-DIMETHYLPHENYL)AMINO)-2-PYRIMIDINYL)AMINO)-, HYDROCHLORIDE (1:1)
Systematic Name English
JULUCA COMPONENT RILPIVIRINE HYDROCHLORIDE
Brand Name English
EVIPLERA COMPONENT RILPIVIRINE HYDROCHLORIDE
Brand Name English
RILPIVIRINE HYDROCHLORIDE [USAN]
Common Name English
RILPIVIRINE HYDROCHLORIDE [VANDF]
Common Name English
RILPIVIRINE (AS HYDROCHLORIDE)
Common Name English
TMC-278 HYDROCHLORIDE
Code English
TMC278 HYDROCHLORIDE
Code English
RILPIVIRINE HYDROCHLORIDE [JAN]
Common Name English
ODEFSEY COMPONENT RILPIVIRINE HYDROCHLORIDE
Common Name English
EDURANT PED
Brand Name English
Rilpivirine hydrochloride [WHO-DD]
Common Name English
RILPIVIRINE HYDROCHLORIDE [MI]
Common Name English
RILPIVIRINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS EVIPLERA (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
NCI_THESAURUS C97453
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
EMA ASSESSMENT REPORTS EDURANT (AUTHORIZED: HIV INFECTIONS)
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID80220320
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
CHEBI
68602
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
FDA UNII
212WAX8KDD
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
EVMPD
SUB31460
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
SMS_ID
100000124142
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
RXCUI
1102287
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL175691
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
PUBCHEM
11711114
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
USAN
XX-61
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
DAILYMED
212WAX8KDD
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
DRUG BANK
DBSALT000152
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
CAS
700361-47-3
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
MERCK INDEX
m9619
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C152217
Created by admin on Mon Mar 31 18:52:09 GMT 2025 , Edited by admin on Mon Mar 31 18:52:09 GMT 2025
PRIMARY
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