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Compound Detail

CHEMBL57

NEVIRAPINE
💊 Approved Drug
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💊 Approved Drug
Cc1ccnc2c1NC(=O)c1cccnc1N2C1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL57
Name NEVIRAPINE
Phase Approved
Structure Type MOL
InChI Key NQDJXKOVJZTUJA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BIRG 0587 BIRG-0587 BIRG0587 Nevirapina Nevirapine Nevirapine anhydrous Nevirapine teva Nevirapine, anhydrous Nevirapinum anhydrous NSC-641530 Viramune Viramune xr
16
Targets
1,088
Activities
3
Assay Types
20
PK Parameters
20
Publications
12
Known Names
6
Indications
1
Mechanisms

Molecular Properties

266.3
MW (Da)
2.65
ALogP
4
HBA
1
HBD
58.1
PSA (Ų)
0.86
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -pine; -vir-
USAN Year 1991

Extended Properties

Molecular Formula C15H14N4O
MW 266.30
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.25

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 Infections Tuberculosis

ATC Classification

J05AG01
nevirapine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
dermatological toxicity
Country: United States

Activity Summary

EC50 606 meas. best 11.0
IC50 442 meas. best 8.3
Ki 40 meas. best 6.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 11.0 6.3231 0.0 531
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 8.44 6.2639 3.6 33
CCRF-CEM
CHEMBL382
 IC50 8.3 6.7077 5.0 13
Unchecked
CHEMBL612545
 EC50 8.17 6.4713 6.7 8
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.0 6.3484 10.0 127
MT4
CHEMBL388
 EC50 7.52 6.5326 30.0 19
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.51 5.4317 31.0 6
MT4
CHEMBL388
 IC50 7.5 5.9077 32.0 13
ADMET
CHEMBL612558
 IC50 7.47 6.54 34.0 7
C8166
CHEMBL614533
 IC50 7.4 7.4 40.0 2
PBMC
CHEMBL613107
 IC50 7.4 7.4 40.0 1
ADMET
CHEMBL612558
 EC50 7.31 7.31 49.4 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 7.3 5.9225 50.0 219
Human immunodeficiency virus
CHEMBL613758
 EC50 7.3 7.215 50.0 2
HeLa
CHEMBL399
 IC50 7.25 5.7969 56.0 13
Unchecked
CHEMBL612545
 IC50 7.04 5.9333 91.0 15
Human immunodeficiency virus type 1 protease
CHEMBL243
 IC50 7.0 5.3967 101.0 3
Human immunodeficiency virus
CHEMBL613758
 IC50 7.0 7.0 100.0 1
CCRF-CEM
CHEMBL382
 EC50 6.96 6.96 110.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.6 5.9133 250.0 6
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Ki 6.52 5.3748 300.0 29
MT2
CHEMBL614184
 IC50 6.52 6.52 303.0 1
Unchecked
CHEMBL612545
 Ki 5.7 4.9167 2000.0 6
H9
CHEMBL614806
 IC50 5.3 5.3 5000.0 1
Human immunodeficiency virus 2
CHEMBL380
 IC50 4.82 4.82 15000.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.19 4.19 64000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 1.2e-05 mL.min-1.g-1 Homo sapiens
CL 1e-06 mL.min-1.g-1 Homo sapiens
CL 0.013 uL/min Homo sapiens
F 80.0 % Homo sapiens
F 93.0 % Homo sapiens
F 90.0 % Homo sapiens
F 95.0 % Homo sapiens
Fu 0.32 - Homo sapiens
Fu 0.32 - Homo sapiens
MRT 81.0 hr Homo sapiens
t1/2 - - Rattus norvegicus
t1/2 - - Rattus norvegicus
T1/2 30.0 hr Homo sapiens
T1/2 30.0 hr Homo sapiens
T1/2 53.0 hr Homo sapiens
T1/2 25.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.01 nM 11.0 Antiviral activity of wild-type Human immunodeficiency virus 1 isolate 5331 by c... 19704127
Human immunodeficiency virus 1 EC50 = 0.02 nM 10.7 Antiviral activity of wild-type Human immunodeficiency virus 1 isolate 5512 by c... 19704127
Human immunodeficiency virus 1 EC50 = 0.703 nM 9.15 Antiviral activity of Human immunodeficiency virus 1 isolate 8117 harboring A98S... 19704127
Human immunodeficiency virus 1 EC50 = 0.7 nM 9.15 Antiviral activity against VSVG/wild-type HIV-1 infected in human HEK 293T cells... 32004936
Human immunodeficiency virus 1 EC50 = 0.852 nM 9.07 Antiviral activity of Human immunodeficiency virus 1 isolate 8116 harboring A98S... 19704127
Human immunodeficiency virus 1 EC50 = 0.997 nM 9.0 Antiviral activity of Human immunodeficiency virus 1 isolate 9225 harboring A98S... 19704127
Human immunodeficiency virus 1 EC50 = 1.5 nM 8.82 Antiviral activity against HIV1RF infected in human CEM-SS cells 18083556
Human immunodeficiency virus 1 EC50 = 1.5 nM 8.82 Antiviral activity against HIV1 RF in CEM-SS cells assessed as inhibition of vir... 18222088
Human immunodeficiency virus 1 EC50 = 3.2 nM 8.49 Antiviral activity against wild type HIV-1 strain 3B infected in human MT4 cells... 31767136
Human immunodeficiency virus 1 EC50 = 3.2 nM 8.49 Antiviral activity against HIV-1 K103N mutant strain infected in human MT4 cells... 31767136
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 3.6 nM 8.44 Inhibition of HIV1 reverse transcriptase by EIA 20137956
CCRF-CEM IC50 = 5.0 nM 8.3 Antiviral activity against site directed resistant isolate HIV-1 K101E in CEM ce... 11708913
Human immunodeficiency virus 1 EC50 = 6.7 nM 8.17 Antiviral activity against HIV-1 E138K mutant strain infected in human MT4 cells... 31767136
Unchecked EC50 = 6.7 nM 8.17 Anti-HIV-1 activity against HTLV-3B infected in human MT2 cells assessed as redu... 31893549
CCRF-CEM IC50 = 8.0 nM 8.1 Antiviral activity against site directed 4X AZT resistant isolate HIV-1 in CEM c... 11708913
Human immunodeficiency virus 1 EC50 = 8.2 nM 8.09 Antiviral activity against 100 TCID50 HIV1 infected in human TZM-b1 cells assess... 20050672
Human immunodeficiency virus 1 EC50 = 8.94 nM 8.05 Antiviral activity against Human immunodeficiency virus 1 subtype AE infected in... 19933797
Human immunodeficiency virus 1 EC50 = 9.32 nM 8.03 Antiviral activity against Human immunodeficiency virus 1 subtype A1 infected in... 19933797
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Antiviral activity against HIV1-3B infected in human MT4 cells assessed as inhib... 25946116
Human immunodeficiency virus 1 IC50 = 10.0 nM 8.0 Antiviral activity against Human immunodeficiency virus 1 3b infected in human M... 24926807

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 460
17116677 10.1128/aac.01032-06 Human immunodeficiency virus 1 93
- 10.5281/zenodo.13943903 ADMET 89
19933797 10.1128/aac.00986-09 Human immunodeficiency virus 1 68
31158845 10.1038/s41586-019-1291-3 ADMET 63
19029331 10.1128/aac.01156-08 Human immunodeficiency virus 1 42
14971897 10.1021/jm030255y Human immunodeficiency virus 1 27
18665583 10.1021/jm8004493 Human immunodeficiency virus 1 25
20194692 10.1128/aac.00870-09 Human immunodeficiency virus 1 24
19289522 10.1128/aac.01559-08 Human immunodeficiency virus 1 21
20008779 10.1128/aac.01335-09 Human immunodeficiency virus 1 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
15481987 10.1021/jm0407658 Human immunodeficiency virus 1 17
15771439 10.1021/jm0408621 Human immunodeficiency virus 1 17
19645483 10.1021/jm900802y Human immunodeficiency virus 1 16
21060108 10.1128/aac.01064-10 Human immunodeficiency virus 1 16
25072874 10.1016/j.ejmech.2014.07.072 Human immunodeficiency virus 1 16
34890994 10.1016/j.bmc.2021.116531 Human immunodeficiency virus 1 15
11384233 10.1021/jm0004906 HeLa 15
29635166 10.1016/j.ejmech.2018.03.059 Human immunodeficiency virus 1 14

Data from ChEMBL 36 via Core Engine