Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL308954

ETRAVIRINE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
Cc1cc(C#N)cc(C)c1Oc1nc(Nc2ccc(C#N)cc2)nc(N)c1Br
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL308954
Name ETRAVIRINE
Phase Approved
Structure Type MOL
InChI Key PYGWGZALEOIKDF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Etravirina Etravirine Intelence R-165335 R165335 TMC 125 TMC-125 TMC125
23
Targets
846
Activities
3
Assay Types
26
PK Parameters
20
Publications
8
Known Names
7
Indications
1
Mechanisms

Molecular Properties

435.3
MW (Da)
4.72
ALogP
7
HBA
2
HBD
120.6
PSA (Ų)
0.61
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2008
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -vir-
USAN Year 2005

Extended Properties

Molecular Formula C20H15BrN6O
MW 435.29
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -1.05

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 HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome Friedreich Ataxia Infections

ATC Classification

J05AG04
etravirine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 643 meas. best 10.3
IC50 202 meas. best 9.22
Kd 1 meas. best 5.84

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 10.3 8.0716 0.1 577
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 9.22 7.5245 0.6 119
Human immunodeficiency virus
CHEMBL613758
 IC50 9.0 8.2425 1.0 16
Unchecked
CHEMBL612545
 IC50 9.0 7.1293 1.0 14
MT4
CHEMBL388
 EC50 9.0 8.4414 1.0 7
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.96 8.193 1.1 23
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 8.7 8.032 2.0 30
Unchecked
CHEMBL612545
 EC50 8.7 7.8989 2.0 9
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 8.62 7.963 2.4 10
Human immunodeficiency virus 2
CHEMBL380
 EC50 7.96 6.605 11.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.56 6.56 277.0 2
Plasmodium falciparum
CHEMBL364
 IC50 6.39 5.832 409.0 5
Cytochrome P450 2C19
CHEMBL3622
 IC50 6.3 6.3 496.0 2
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Kd 5.84 5.84 1460.0 1
Cruzipain
CHEMBL3563
 IC50 5.4 5.4 4000.0 1
ATP-binding cassette sub-family C member 3
CHEMBL5918
 IC50 5.29 5.29 5100.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 5.22 5.22 6000.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 5.13 5.13 7480.0 2
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.12 5.12 7600.0 1
ATP-binding cassette sub-family C member 2
CHEMBL5748
 IC50 5.11 5.11 7800.0 1
Multidrug resistance-associated protein 1
CHEMBL3004
 IC50 5.07 5.07 8500.0 1
ADMET
CHEMBL612558
 IC50 5.03 5.03 9400.0 1
MT2
CHEMBL614184
 EC50 4.96 4.96 11000.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.92 4.92 12000.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.6 4.6 25118.9 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.38 4.38 41300.0 2
Leishmania infantum
CHEMBL612848
 IC50 4.38 4.38 41650.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 600.0 ng.hr.mL-1 Rattus norvegicus
AUC 400.0 ng.hr.mL-1 Homo sapiens
AUC 6216.0 ng.hr Homo sapiens
AUC 6813.0 ng.hr Homo sapiens
CL 29.0 mL.min-1.g-1 Homo sapiens
CL 4.167 mL.min-1.kg-1 Homo sapiens
CL 21.2 mL.min-1.g-1 Homo sapiens
CL 19.0 mL.min-1.kg-1 Homo sapiens
Cmax 1686.23 nM Homo sapiens
Cmax 1759.75 nM Homo sapiens
Cmax 3078.41 nM Homo sapiens
F 13.3 % Canis lupus familiaris
F 13.0 % Canis lupus familiaris
F - % Rattus norvegicus
F - % Rattus norvegicus
F - % Rattus norvegicus
Ka 0.8 10'4/M/s Human immunodeficiency virus 1
T1/2 2.333 hr Homo sapiens
T1/2 8.87 hr Canis lupus familiaris
T1/2 8.87 hr Canis lupus familiaris
T1/2 30.0 hr -
T1/2 41.0 hr Homo sapiens
T1/2 4.818 hr Homo sapiens
T1/2 1.092 hr Homo sapiens
Tmax 4.0 hr Homo sapiens
Tmax 4.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.05 nM 10.3 Antiviral activity against HIV1 NL4-3 infected in human MT2 cells assessed as in... 20660667
Human immunodeficiency virus 1 EC50 = 0.21 nM 9.68 Antiviral activity against Human immunodeficiency virus 1 subtype E isolate 93TH... 19933797
Human immunodeficiency virus 1 EC50 = 0.24 nM 9.62 Antiviral activity against Human immunodeficiency virus 1 subtype G infected in ... 19933797
Human immunodeficiency virus 1 EC50 = 0.35 nM 9.46 Antiviral activity against Human immunodeficiency virus 1 subtype F1 infected in... 19933797
Human immunodeficiency virus 1 EC50 = 0.4 nM 9.4 Antiviral activity against NNRTI-resistant HIV1 harboring reverse transcriptase ... 23137340
Human immunodeficiency virus 1 EC50 = 0.43 nM 9.37 Antiviral activity against Human immunodeficiency virus 1 subtype B isolate WEJO... 19933797
Human immunodeficiency virus 1 EC50 = 0.44 nM 9.36 Antiviral activity against Human immunodeficiency virus 1 subtype D isolate 92UG... 19933797
Human immunodeficiency virus 1 EC50 = 0.46 nM 9.34 Antiviral activity against Human immunodeficiency virus 1 subtype AG infected in... 19933797
Human immunodeficiency virus 1 EC50 = 0.46 nM 9.34 Antiviral activity against Human immunodeficiency virus 1 subtype F isolate 93BR... 19933797
Human immunodeficiency virus 1 EC50 = 0.48 nM 9.32 Antiviral activity against Human immunodeficiency virus 1 subtype A isolate 92RW... 19933797
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against Human immunodeficiency virus 1 subtype E isolate 92TH... 19933797
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against recombinant HIV1 harboring reverse transcriptase V106... 20124001
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against HIV1 NL4-3 infected in human MT2 cells assessed as in... 20660667
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against wild type HIV 1 NL4-3 infected in human MT4 cells ass... 30525601
Human immunodeficiency virus 1 EC50 = 0.51 nM 9.29 Antiviral activity against Human immunodeficiency virus 1 subtype (H) infected i... 19933797
Human immunodeficiency virus 1 EC50 = 0.52 nM 9.28 Antiviral activity against Human immunodeficiency virus 1 subtype C infected in ... 19933797
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 0.6 nM 9.22 Inhibition of HIV1 isolate R8 reverse transcriptase after 90 mins 19289522
Human immunodeficiency virus 1 EC50 = 0.6 nM 9.22 Antiviral activity against HIV1 expressing wild type reverse transcriptase infec... 23137340
Human immunodeficiency virus 1 EC50 = 0.65 nM 9.19 Antiviral activity against Human immunodeficiency virus 1 subtype AE infected in... 19933797
Human immunodeficiency virus 1 EC50 = 0.66 nM 9.18 Antiviral activity against Human immunodeficiency virus 1 subtype G isolate G3 i... 19933797

Literature References

PubMed DOI Target Context # Activities
19933797 10.1128/aac.00986-09 Human immunodeficiency virus 1 92
32293182 10.1021/acs.jmedchem.0c00117 Human immunodeficiency virus 1 21
20008779 10.1128/aac.01335-09 Human immunodeficiency virus 1 20
19289522 10.1128/aac.01559-08 Human immunodeficiency virus 1 17
28481112 10.1021/acs.jmedchem.7b00332 Unchecked 16
21189339 10.1128/aac.01527-10 LS180 16
19007201 10.1021/jm800527x Human immunodeficiency virus 16
34890994 10.1016/j.bmc.2021.116531 Human immunodeficiency virus 1 15
36700940 10.1021/acs.jmedchem.2c01875 Human immunodeficiency virus 1 15
30624934 10.1021/acs.jmedchem.8b01656 Human immunodeficiency virus 1 14
37255025 10.1021/acs.jmedchem.3c00275 ADMET 14
29635166 10.1016/j.ejmech.2018.03.059 Human immunodeficiency virus 1 14
25418038 10.1021/jm5011622 Human immunodeficiency virus 1 12
24805780 10.1021/jm500139a Human immunodeficiency virus 1 11
19704127 10.1128/aac.00800-09 Human immunodeficiency virus 1 11
20124001 10.1128/aac.01480-09 Human immunodeficiency virus 1 11
20660667 10.1128/aac.01455-09 Human immunodeficiency virus 1 10
21872971 10.1016/j.ejmech.2011.08.011 Human immunodeficiency virus 1 10
23137340 10.1021/jm301294g Human immunodeficiency virus 1 10
30525601 10.1021/acs.jmedchem.8b01238 Human immunodeficiency virus 1 10

Data from ChEMBL 36 via Core Engine