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Compound Detail

CHEMBL70663

DAPIVIRINE
🧪 Phase III
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🧪 Phase III
Cc1cc(C)c(Nc2ccnc(Nc3ccc(C#N)cc3)n2)c(C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL70663
Name DAPIVIRINE
Phase Phase III
Structure Type MOL
InChI Key ILAYIAGXTHKHNT-UHFFFAOYSA-N

Known Names

AIDS-105293 Dapivirina Dapivirine Gel-02 R-147681 TMC-120 Tmc120
8
Targets
126
Activities
2
Assay Types
2
PK Parameters
20
Publications
7
Known Names
4
Indications
1
Mechanisms

Molecular Properties

329.4
MW (Da)
4.76
ALogP
5
HBA
2
HBD
73.6
PSA (Ų)
0.72
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -vir-
USAN Year 2014

Extended Properties

Molecular Formula C20H19N5
MW 329.41
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.57

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 Acquired Immunodeficiency Syndrome Infections

ATC Classification

G01AX17
dapivirine
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS

Activity Summary

EC50 75 meas. best 10.98
IC50 51 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 10.98 8.3297 0.0 64
Human immunodeficiency virus 1
CHEMBL378
 IC50 10.0 8.7739 0.1 28
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 9.0 7.0159 1.0 17
MT4
CHEMBL388
 EC50 9.0 7.9883 1.0 6
Unchecked
CHEMBL612545
 IC50 6.39 6.355 404.0 2
SARS-CoV-2
CHEMBL4303835
 IC50 6.14 6.14 730.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 5.9 5.9 1250.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.31 5.31 4880.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.71 4.71 19500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 19400.0 ng.hr.mL-1 Rattus norvegicus
AUC 4700.0 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.0105 nM 10.98 Antiviral activity of wild-type Human immunodeficiency virus 1 isolate 5512 by c... 19704127
Human immunodeficiency virus 1 EC50 = 0.03 nM 10.52 Antiviral activity against wild type HIV 1 NL4-3 infected in human MT4 cells ass... 21438533
Human immunodeficiency virus 1 IC50 = 0.1 nM 10.0 Antiviral activity against HIV-1 Bal infected in human PM1 cells assessed as inh... 19029331
Human immunodeficiency virus 1 IC50 = 0.15 nM 9.82 Antiviral activity against R5 tropic HIV1 YU.2 infected in human TZM-b1 cells af... 19258271
Human immunodeficiency virus 1 IC50 = 0.19 nM 9.72 Antiviral activity against R5 tropic HIV1 R8.BaL infected in human TZM-b1 cells ... 19258271
Human immunodeficiency virus 1 IC50 = 0.2 nM 9.7 Antiviral activity against HIV-1 Bal infected in 1 hr compound pretreated human ... 19029331
Human immunodeficiency virus 1 EC50 = 0.298 nM 9.53 Antiviral activity against HIV1 RTMDR1 infected in human TZM-bl cells assessed a... 19666220
Human immunodeficiency virus 1 EC50 = 0.3 nM 9.52 Antiviral activity against multidrug-resistant HIV 1 IRLL98 harboring reverse tr... 21438533
Human immunodeficiency virus 1 IC50 = 0.37 nM 9.43 Antiviral activity against X4 tropic HIV1 NL4.3 infected in human TZM-b1 cells a... 19258271
Human immunodeficiency virus 1 IC50 = 0.53 nM 9.28 Antiviral activity against X4 tropic HIV1 3B infected in human TZM-b1 cells afte... 19258271
Human immunodeficiency virus 1 EC50 = 0.6 nM 9.22 Antiviral activity against wild type HIV1 NL4-3 infected in human MT4 cells asse... 22428851
Human immunodeficiency virus 1 EC50 = 0.6 nM 9.22 Antiviral activity against wild type HIV 1 NL4-3 infected in human MT4 cells ass... 30525601
Human immunodeficiency virus 1 EC50 = 0.62 nM 9.21 Antiviral activity against HIV1 NL4-3 infected in human TZM-bl cells assessed as... 19666220
Human immunodeficiency virus 1 EC50 = 0.7 nM 9.15 Antiviral activity against wild type HIV1 3B infected in human MT2 cells assesse... 23937980
Human immunodeficiency virus 1 IC50 = 0.8 nM 9.1 Antiviral activity against R5 tropic HIV1 BaL infected in human TZM-b1 cells aft... 19258271
Human immunodeficiency virus 1 IC50 = 0.84 nM 9.08 Antiviral activity against X4 tropic HIV1 RF infected in human TZM-b1 cells afte... 19258271
Human immunodeficiency virus 1 IC50 = 0.9 nM 9.05 Antiviral activity against HIV-1 3B infected in human MT4 cells after 7 days by ... 19029331
Human immunodeficiency virus 1 EC50 = 0.91 nM 9.04 Antiviral activity against HIV 1 subtype B harboring wild type reverse transcrip... 20308384
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Potency evaluated against wild type HIV-1 strain IIIB 15115397
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against zidovudine-resistant HIV1 harboring RT 67N, 70R, 215F... 24805780

Literature References

PubMed DOI Target Context # Activities
19029331 10.1128/aac.01156-08 Human immunodeficiency virus 1 76
24805780 10.1021/jm500139a Human immunodeficiency virus 1 23
19258271 10.1128/aac.01096-08 Human immunodeficiency virus 1 13
30525601 10.1021/acs.jmedchem.8b01238 Human immunodeficiency virus 1 11
23084903 10.1016/j.bmcl.2012.09.066 Human immunodeficiency virus 1 10
19704127 10.1128/aac.00800-09 Human immunodeficiency virus 1 9
21438533 10.1021/jm101626c Human immunodeficiency virus 1 9
11527705 10.1016/s0960-894x(01)00412-7 Human immunodeficiency virus 1 7
30223123 10.1016/j.ejmech.2018.09.013 Human immunodeficiency virus type 1 reverse transcriptase 7
15771411 10.1021/jm040127p MT4 7
22428851 10.1021/jm201308v Human immunodeficiency virus 1 7
15771434 10.1021/jm040840e Human immunodeficiency virus 1 7
15115397 10.1021/jm030558s Human immunodeficiency virus 1 7
19029331 10.1128/aac.01156-08 Unchecked 6
22428851 10.1021/jm201308v Human immunodeficiency virus type 1 reverse transcriptase 6
21930388 10.1016/j.bmc.2011.08.060 Human immunodeficiency virus 1 6
23937980 10.1016/j.bmcl.2013.06.091 Human immunodeficiency virus 1 6
19704127 10.1128/aac.00800-09 Human immunodeficiency virus type 1 reverse transcriptase 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
21438533 10.1021/jm101626c Human immunodeficiency virus type 1 reverse transcriptase 5

Data from ChEMBL 36 via Core Engine