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
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+;
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
150 mg 1 times / day multiple, oral Highest studied dose Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.62 |
unhealthy, 21–66 n = 91 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21–66 Sex: M+F Population Size: 91 Sources: Page: p.62 |
Disc. AE: Alanine aminotransferase increase, Aspartate aminotransferase increased... AEs leading to discontinuation/dose reduction: Alanine aminotransferase increase Sources: Page: p.62Aspartate aminotransferase increased |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy n = 686 Health Status: unhealthy Condition: HIV-1 infection Population Size: 686 Sources: Page: p.1 |
Disc. AE: Depressive disorders, Suicide attempt... AEs leading to discontinuation/dose reduction: Depressive disorders (severe, 1%) Sources: Page: p.1Suicide attempt (0.29%) |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.3 |
unhealthy n = 686 Health Status: unhealthy Condition: HIV-1 infection Population Size: 686 Sources: Page: p.3 |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (0.1%) Sources: Page: p.3 |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Disc. AE: Fat redistribution, Immune reconstitution syndrome... AEs leading to discontinuation/dose reduction: Fat redistribution Sources: Page: p.1Immune reconstitution syndrome |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Alanine aminotransferase increase | Disc. AE | 150 mg 1 times / day multiple, oral Highest studied dose Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.62 |
unhealthy, 21–66 n = 91 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21–66 Sex: M+F Population Size: 91 Sources: Page: p.62 |
Aspartate aminotransferase increased | Disc. AE | 150 mg 1 times / day multiple, oral Highest studied dose Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: Page: p.62 |
unhealthy, 21–66 n = 91 Health Status: unhealthy Condition: HIV-1 infection Age Group: 21–66 Sex: M+F Population Size: 91 Sources: Page: p.62 |
Suicide attempt | 0.29% Disc. AE |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy n = 686 Health Status: unhealthy Condition: HIV-1 infection Population Size: 686 Sources: Page: p.1 |
Depressive disorders | severe, 1% Disc. AE |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy n = 686 Health Status: unhealthy Condition: HIV-1 infection Population Size: 686 Sources: Page: p.1 |
Rash | 0.1% Disc. AE |
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.3 |
unhealthy n = 686 Health Status: unhealthy Condition: HIV-1 infection Population Size: 686 Sources: Page: p.3 |
Fat redistribution | Disc. AE | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
Immune reconstitution syndrome | Disc. AE | 25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: HIV-1 infection Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
Rational design of potent non-nucleoside inhibitors of HIV-1 reverse transcriptase. | 2012 Dec 13 |
|
Update on rilpivirine: a new potent non-nucleoside reverse transcriptase inhibitor (NNRTI) of HIV replication. | 2013 May |
|
In vitro and in vivo activities of AIC292, a novel HIV-1 nonnucleoside reverse transcriptase inhibitor. | 2013 Nov |
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
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).
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Classification Tree | Code System | Code | ||
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EMA ASSESSMENT REPORTS |
EVIPLERA (AUTHORIZED: HIV INFECTIONS)
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NCI_THESAURUS |
C97453
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EMA ASSESSMENT REPORTS |
EDURANT (AUTHORIZED: HIV INFECTIONS)
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ACTIVE MOIETY
SUBSTANCE RECORD