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
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+
Molecular Formula | C22H18N6 |
Molecular Weight | 366.4185 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=19933797
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
Sources: http://napwha.org.au/treatment/rilpivirine
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Reverse transcriptase/RNaseH (UniProtKB: Q72547) |
14.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EDURANT Approved UseIn 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 Date2011 |
Cmax
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 |
Funbound
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=19933797
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
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Mon Mar 31 18:26:13 GMT 2025
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Record UNII |
FI96A8X663
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Validated (UNII)
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WHO-ATC |
J05AG05
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WHO-ATC |
J05AR08
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FDA ORPHAN DRUG |
858321
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NDF-RT |
N0000175463
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NCI_THESAURUS |
C97453
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WHO-VATC |
QJ05AG05
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WHO-ATC |
J05AR19
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LIVERTOX |
NBK548514
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WHO-ATC |
J05AR21
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WHO-VATC |
QJ05AR08
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C76929
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m9619
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WW-86
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SUB31456
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1102270
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DTXSID10198189
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FI96A8X663
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RILPIVIRINE
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Rilpivirine
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68606
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CHEMBL175691
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4174
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FI96A8X663
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
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EXCRETED UNCHANGED |
FECAL
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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TARGET ORGANISM->INHIBITOR |
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Blood-to-plasma ratio | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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oral administration |
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