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Compound Detail

CHEMBL175691

RILPIVIRINE
💊 Approved Drug
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💊 Approved Drug
Cc1cc(/C=C/C#N)cc(C)c1Nc1ccnc(Nc2ccc(C#N)cc2)n1

Basic Information

ChEMBL ID CHEMBL175691
Name RILPIVIRINE
Phase Approved
Structure Type MOL
InChI Key YIBOMRUWOWDFLG-ONEGZZNKSA-N
Therapeutic ✓ Yes

Known Names

Edurant R 278474 R-278474 R278474 Rekambys Rilpivirina Rilpivirine Rilpivirine component of cabenuva TMC-278 TMC278
15
Targets
281
Activities
2
Assay Types
30
PK Parameters
20
Publications
10
Known Names
6
Indications
1
Mechanisms

Molecular Properties

366.4
MW (Da)
4.99
ALogP
6
HBA
2
HBD
97.4
PSA (Ų)
0.62
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -vir-
USAN Year 2009

Extended Properties

Molecular Formula C22H18N6
MW 366.43
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -1.13

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 reverse transcriptase inhibitor INHIBITOR Human immunodeficiency virus type 1 reverse transcriptase

Indications

HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome Hepatitis C Insulin Resistance

ATC Classification

J05AG05
rilpivirine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 195 meas. best 10.15
IC50 86 meas. best 9.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
EC50 10.15 8.7681 0.1 183
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
EC50 9.7 9.1 0.2 7
Human immunodeficiency virus 1
CHEMBL378
IC50 9.48 8.515 0.3 8
Human immunodeficiency virus
CHEMBL613758
IC50 9.46 9.46 0.3 1
Unchecked
CHEMBL612545
EC50 9.36 8.99 0.4 2
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
IC50 9.17 7.5076 0.7 21
Unchecked
CHEMBL612545
IC50 9.0 9.0 1.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 6.47 6.47 335.0 8
Cytochrome P450 2C9
CHEMBL3397
IC50 6.46 6.46 346.0 8
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.3 6.2089 500.0 9
Plasmodium falciparum
CHEMBL364
IC50 5.96 5.875 1096.0 4
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 5.82 5.82 1500.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.66 5.66 2170.0 8
Cytochrome P450 2D6
CHEMBL289
IC50 5.47 5.47 3410.0 8
ADMET
CHEMBL612558
EC50 5.36 5.36 4400.0 1
Human immunodeficiency virus 2
CHEMBL380
EC50 5.28 5.28 5220.0 1
MT2
CHEMBL614184
EC50 5.1 5.1 8000.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 5.04 5.04 9110.0 8

Pharmacokinetic Data

Parameter Value Units Species
AUC 3100.0 ng.hr.mL-1 Rattus norvegicus
AUC 8700.0 ng.hr.mL-1 Canis lupus familiaris
AUC 1400.0 ng.hr.mL-1 Cercopithecidae
AUC 44000.0 ng.hr.mL-1 Oryctolagus cuniculus
AUC 9800.0 ng.hr.mL-1 Rattus norvegicus
AUC 9650.0 ng.hr.mL-1 Rattus norvegicus
AUC 23790.0 ng.hr.mL-1 Canis lupus familiaris
AUC 1230.0 ng.hr.mL-1 Rattus norvegicus
AUC 3840.0 ng.hr.mL-1 Rattus norvegicus
AUC 15300.0 ng.hr.mL-1 Rattus norvegicus
AUC 3540.0 ng.hr.mL-1 Rattus norvegicus
AUC 15500.0 ng.hr.mL-1 Rattus norvegicus
AUC 117000.0 ng.hr.mL-1 Rattus norvegicus
AUC 188000.0 ng.hr.mL-1 Rattus norvegicus
AUC 109000.0 ng.hr.mL-1 Rattus norvegicus
AUC 20400.0 ng.hr.mL-1 Rattus norvegicus
AUC 56800.0 ng.hr.mL-1 Rattus norvegicus
AUC 10500.0 ng.hr.mL-1 Rattus norvegicus
AUC 70600.0 ng.hr.mL-1 Rattus norvegicus
AUC 109000.0 ng.hr.mL-1 Rattus norvegicus
AUC 148000.0 ng.hr.mL-1 Rattus norvegicus
AUC 281000.0 ng.hr.mL-1 Rattus norvegicus
AUC 121000.0 ng.hr.mL-1 Rattus norvegicus
AUC 265000.0 ng.hr.mL-1 Rattus norvegicus
AUC 97800.0 ng.hr.mL-1 Rattus norvegicus
AUC 219000.0 ng.hr.mL-1 Rattus norvegicus
AUC 134000.0 ng.hr.mL-1 Rattus norvegicus
AUC 234000.0 ng.hr.mL-1 Rattus norvegicus
AUC 8661.0 ng.hr.mL-1 Canis lupus familiaris
AUC 23200.0 ng.hr.mL-1 Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.07 nM 10.15 Antiviral activity against Human immunodeficiency virus 1 subtype D isolate 92UG... 19933797
Human immunodeficiency virus 1 EC50 = 0.07 nM 10.15 Antiviral activity against Human immunodeficiency virus 1 subtype A isolate 92RW... 19933797
Human immunodeficiency virus 1 EC50 = 0.07 nM 10.15 Antiviral activity against Human immunodeficiency virus 1 subtype E isolate 93TH... 19933797
Human immunodeficiency virus 1 EC50 = 0.08 nM 10.1 Antiviral activity against Human immunodeficiency virus 1 subtype B isolate WEJO... 19933797
Human immunodeficiency virus 1 EC50 = 0.08 nM 10.1 Antiviral activity against Human immunodeficiency virus 1 subtype E isolate 92TH... 19933797
Human immunodeficiency virus 1 EC50 = 0.1 nM 10.0 Effective concentration against human immunodeficiency virus type 1 G190S mutant... 15771434
Human immunodeficiency virus 1 EC50 = 0.1 nM 10.0 Antiviral activity against HIV1 LAI with RT K103N mutation in MT4 cells by EGFP ... 17223230
Human immunodeficiency virus 1 EC50 = 0.11 nM 9.96 Antiviral activity against Human immunodeficiency virus 1 subtype C isolate 93MW... 19933797
Human immunodeficiency virus 1 EC50 = 0.13 nM 9.89 Antiviral activity against Human immunodeficiency virus 1 subtype AG infected in... 19933797
Human immunodeficiency virus 1 EC50 = 0.14 nM 9.85 Antiviral activity against Human immunodeficiency virus 1 subtype G infected in ... 19933797
Human immunodeficiency virus 1 EC50 = 0.16 nM 9.8 Antiviral activity against Human immunodeficiency virus 1 subtype F isolate 93BR... 19933797
Human immunodeficiency virus 1 EC50 = 0.19 nM 9.72 Antiviral activity against Human immunodeficiency virus 1 subtype F isolate 93BR... 19933797
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 0.2 nM 9.7 Inhibition of HIV-1 reverse transcriptase K103N mutant assessed as reduction in ... 35175760
Human immunodeficiency virus 1 EC50 = 0.21 nM 9.68 Antiviral activity against Human immunodeficiency virus 1 subtype AE infected in... 19933797
Human immunodeficiency virus 1 EC50 = 0.21 nM 9.68 Antiviral activity against Human immunodeficiency virus 1 subtype F1 infected in... 19933797
Human immunodeficiency virus 1 EC50 = 0.22 nM 9.66 Antiviral activity against Human immunodeficiency virus 1 subtype BG infected in... 19933797
Human immunodeficiency virus 1 EC50 = 0.23 nM 9.64 Antiviral activity against Human immunodeficiency virus 1 subtype B isolate 93BR... 19933797
Human immunodeficiency virus 1 EC50 = 0.24 nM 9.62 Antiviral activity against Human immunodeficiency virus 1 subtype A isolate 92UG... 19933797
Human immunodeficiency virus 1 EC50 = 0.24 nM 9.62 Antiviral activity against Human immunodeficiency virus 1 subtype (H) infected i... 19933797
Human immunodeficiency virus 1 EC50 = 0.25 nM 9.6 Antiviral activity against Human immunodeficiency virus 1 subtype G isolate G3 i... 19933797

Literature References

PubMed DOI Target Context # Activities
20160045 10.1128/aac.01529-09 ADMET 126
19933797 10.1128/aac.00986-09 Human immunodeficiency virus 1 122
20160045 10.1128/aac.01529-09 Rattus norvegicus 65
20160045 10.1128/aac.01529-09 Plasma 30
20160045 10.1128/aac.01529-09 Canis familiaris 24
32293182 10.1021/acs.jmedchem.0c00117 Human immunodeficiency virus 1 21
37130343 10.1021/acs.jmedchem.2c02055 ADMET 11
23137340 10.1021/jm301294g Human immunodeficiency virus 1 10
15771449 10.1021/jm040838n Human immunodeficiency virus 1 10
17223230 10.1016/j.ejmech.2006.11.014 Human immunodeficiency virus 1 9
33734714 10.1021/acs.jmedchem.1c00268 Human immunodeficiency virus 1 9
34432448 10.1021/acs.jmedchem.1c01015 Human immunodeficiency virus 1 8
36411036 10.1021/acs.jmedchem.2c00576 Human immunodeficiency virus 1 8
32293182 10.1021/acs.jmedchem.0c00117 Unchecked 8
35061384 10.1021/acs.jmedchem.1c01885 Human immunodeficiency virus 1 8
34432448 10.1021/acs.jmedchem.1c01015 ADMET 8
15771434 10.1021/jm040840e ADMET 8
32293182 10.1021/acs.jmedchem.0c00117 Human immunodeficiency virus type 1 reverse transcriptase 8
22856541 10.1021/jm3007678 Human immunodeficiency virus 1 7
15771434 10.1021/jm040840e Human immunodeficiency virus 1 7

Data from ChEMBL 36 via Core Engine