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Compound Detail

CHEMBL593

DELAVIRDINE
💊 Approved Drug
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💊 Approved Drug
CC(C)Nc1cccnc1N1CCN(C(=O)c2cc3cc(NS(C)(=O)=O)ccc3[nH]2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL593
Name DELAVIRDINE
Phase Approved
Structure Type MOL
InChI Key WHBIGIKBNXZKFE-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Delavirdina Delavirdine U-90152
14
Targets
220
Activities
2
Assay Types
13
PK Parameters
20
Publications
3
Known Names
2
Indications

Molecular Properties

456.6
MW (Da)
2.72
ALogP
6
HBA
3
HBD
110.4
PSA (Ų)
0.53
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -vir-
USAN Year 1994

Extended Properties

Molecular Formula C22H28N6O3S
MW 456.57
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -1.75

Indications

Virus Diseases HIV Infections

ATC Classification

J05AG02
delavirdine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 114 meas. best 8.0
IC50 106 meas. best 9.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium yoelii yoelii
CHEMBL612328
 IC50 9.07 9.07 0.8 2
Human immunodeficiency virus type 1 protease
CHEMBL243
 IC50 8.89 8.89 1.3 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 8.1 6.2584 8.0 25
ADMET
CHEMBL612558
 IC50 8.05 6.52 9.0 11
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.0 6.3002 10.0 105
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.0 6.2229 10.0 42
HeLa
CHEMBL399
 IC50 7.46 5.949 35.0 10
Unchecked
CHEMBL612545
 IC50 7.44 7.27 36.0 2
Unchecked
CHEMBL612545
 EC50 7.43 7.43 37.0 1
MT4
CHEMBL388
 EC50 7.2 5.998 63.0 5
MT4
CHEMBL388
 IC50 7.2 6.0614 63.0 7
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 7.12 7.12 76.0 1
H9
CHEMBL614806
 IC50 6.4 6.4 400.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.21 6.195 610.0 2
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 4.73 4.73 18700.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.19 4.19 64000.0 1
Malate dehydrogenase, cytoplasmic
CHEMBL3560
 IC50 4.07 4.07 85000.0 1
Beta-lactamase
CHEMBL2026
 IC50 4.05 4.05 90000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 13.6 mL.min-1.kg-1 -
CL 13.6 mL.min-1.kg-1 -
F 64.0 % -
F 64.0 % -
F 96.0 % Homo sapiens
Fu 0.016 - Rattus norvegicus
Fu 0.022 - Rattus norvegicus
T1/2 0.18 hr -
T1/2 1.0 hr -
T1/2 1.0 hr -
T1/2 0.18 hr -
T1/2 2.0 hr Homo sapiens
Vd 40.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium yoelii yoelii IC50 = 0.846 nM 9.07 Antimicrobial activity against Plasmodium yoelii 265 liver infected in mammalian... 18212104
Plasmodium yoelii yoelii IC50 = 0.846 nM 9.07 Antimalarial activity against liver stages of Plasmodium yoelii yoelii 22122518
Human immunodeficiency virus type 1 protease IC50 = 1.3 nM 8.89 Inhibition of HIV-1 protease 38516587
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 8.0 nM 8.1 HIV-1 reverse transcriptase inhibitory activity against Wild Type Reverse transc... 10514285
ADMET IC50 = 9.0 nM 8.05 Inhibitory activity of compound on p24 production in peripheral blood mononuclea... 10386942
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 9.0 nM 8.05 HIV-1 reverse transcriptase inhibitory activity against Ile 100 mutant using (po... 10514285
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 9.0 nM 8.05 HIV-1 reverse transcriptase inhibitory activity against Cys181 mutant using (pol... 10514285
ADMET IC50 = 9.0 nM 8.05 Inhibit the replication of the HIV-1 strain HTLV111B in human peripheral blood m... 10999473
ADMET IC50 = 9.0 nM 8.05 Anti-HIV activity by its ability to inhibit the replication of HIV-1 strain HTLV... 10509923
ADMET IC50 = 9.0 nM 8.05 Ability to inhibit the replication of HTLV IIIb strain of HIV-1 p24 antigen prod... 10617082
Human immunodeficiency virus 1 EC50 = 10.0 nM 8.0 Dose required to achieve 50% protection of MT-4 cells from HIV-1 induced cytopat... 11931611
Human immunodeficiency virus 1 IC50 = 10.0 nM 8.0 Antiviral activity against E138K strain of HIV-1 14971897
Human immunodeficiency virus 1 IC50 = 11.0 nM 7.96 Antiviral activity against P225H strain of HIV-1 14971897
Human immunodeficiency virus 1 EC50 = 16.0 nM 7.8 Potency evaluated against wild type HIV-1 strain IIIB 15115397
Human immunodeficiency virus 1 EC50 = 16.0 nM 7.8 Antiviral activity against wild type HIV1 3B infected in human MT4 cells assesse... 22037050
Human immunodeficiency virus 1 EC50 = 16.0 nM 7.8 Antiviral activity against HIV1 3B harboring wild type RT infected in MT4 cells ... 22575532
Human immunodeficiency virus 1 IC50 = 21.0 nM 7.68 Antiviral activity against NNRTI-resistant HIV1 with reverse transcriptase G190A... 18665583
Human immunodeficiency virus 1 EC50 = 21.0 nM 7.68 Antiviral activity against HIV1 by cell-based assay 18314335
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 21.0 nM 7.68 Inhibitory concentration against wild-type reverse transcriptase of HIV-1 14971897
Human immunodeficiency virus 1 EC50 = 21.0 nM 7.68 Antiviral activity against HIV1 27658796

Literature References

PubMed DOI Target Context # Activities
19029331 10.1128/aac.01156-08 Human immunodeficiency virus 1 42
20194692 10.1128/aac.00870-09 Human immunodeficiency virus 1 24
14971897 10.1021/jm030255y Human immunodeficiency virus 1 21
18665583 10.1021/jm8004493 Human immunodeficiency virus 1 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
29635166 10.1016/j.ejmech.2018.03.059 Human immunodeficiency virus 1 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15771449 10.1021/jm040838n Human immunodeficiency virus 1 10
15537347 10.1021/jm040072r HeLa 10
20598556 10.1016/j.bmc.2010.05.081 Human immunodeficiency virus 1 9
17223230 10.1016/j.ejmech.2006.11.014 Human immunodeficiency virus 1 9
10514285 10.1021/jm990095j Human immunodeficiency virus type 1 reverse transcriptase 8
27750153 10.1016/j.ejmech.2016.10.009 Human immunodeficiency virus 1 8
27501911 10.1016/j.bmc.2016.07.041 Human immunodeficiency virus 1 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
14643315 10.1016/j.bmcl.2003.09.045 MT4 7
15115397 10.1021/jm030558s Human immunodeficiency virus 1 7
26802545 10.1016/j.ejmech.2015.11.039 Human immunodeficiency virus 1 7
29635166 10.1016/j.ejmech.2018.03.059 Unchecked 7
15771411 10.1021/jm040127p MT4 7

Data from ChEMBL 36 via Core Engine