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Compound Detail

CHEMBL2364608

DORAVIRINE
💊 Approved Drug
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💊 Approved Drug
Cn1c(Cn2ccc(C(F)(F)F)c(Oc3cc(Cl)cc(C#N)c3)c2=O)n[nH]c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2364608
Name DORAVIRINE
Phase Approved
Structure Type MOL
InChI Key ZIAOVIPSKUPPQW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Doravirina Doravirine Doravirine component of delstrigo MK-1439 Mk-1439a Pifeltro
4
Targets
27
Activities
2
Assay Types
9
PK Parameters
20
Publications
6
Known Names
4
Indications
1
Mechanisms

Molecular Properties

425.8
MW (Da)
2.65
ALogP
7
HBA
1
HBD
105.7
PSA (Ų)
0.69
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2018
Availability Prescription
Chirality Achiral

Routes of Administration

Oral
USAN Stem -vir-
USAN Year 2013

Extended Properties

Molecular Formula C17H11ClF3N5O3
MW 425.75
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.65

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 reverse transcriptase negative allosteric modulator NEGATIVE ALLOSTERIC MODULATOR Human immunodeficiency virus type 1 reverse transcriptase ✓ ✓

Indications

HIV Infections HIV Infections Virus Diseases Kidney Diseases

ATC Classification

J05AG06
doravirine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 23 meas. best 8.18
IC50 4 meas. best 7.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.18 7.2636 6.6 22
Unchecked
CHEMBL612545
 IC50 7.96 7.96 11.0 1
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 7.72 7.54 19.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.06 4.06 88000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.36 mL.min-1.kg-1 Canis lupus familiaris
CL 5.4 mL.min-1.kg-1 Rattus norvegicus
F 52.0 % Canis lupus familiaris
F 57.0 % Rattus norvegicus
T1/2 37.0 hr Canis lupus familiaris
T1/2 4.4 hr Rattus norvegicus
T1/2 11.0 hr Homo sapiens
Vd 1.2 L.kg-1 Canis lupus familiaris
Vd 2.3 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 6.6 nM 8.18 Antiviral activity against HIV-1 L100I mutant infected in human MT4 cells assess... 35797898
Human immunodeficiency virus 1 EC50 = 7.5 nM 8.12 Antiviral activity against HIV-1 E138K mutant infected in human MT4 cells assess... 35797898
Human immunodeficiency virus 1 EC50 = 8.0 nM 8.1 Antiviral activity against wild type HIV-1 IIIB infected in human MT4 cells asse... 38613773
Unchecked IC50 = 11.0 nM 7.96 Inhibition of HIV wild-type reverse transcriptase by electrochemiluminescence as... 24412110
Human immunodeficiency virus 1 EC50 = 13.0 nM 7.89 Antiviral activity against wild type HIV1 3B infected in human MT4 cells assesse... 30606670
Human immunodeficiency virus 1 EC50 = 13.0 nM 7.89 Antiviral activity against HIV1 3B infected in human MT4 cells assessed as prote... 34496571
Human immunodeficiency virus 1 EC50 = 13.0 nM 7.89 Antiviral activity against HIV-1 IIIB infected in human MT4 cells assessed as re... 35797898
Human immunodeficiency virus 1 EC50 = 13.0 nM 7.89 Antiviral activity against NNRTI-resistant HIV-1 harboring L100I mutant infected... 38613773
Human immunodeficiency virus 1 EC50 = 13.3 nM 7.88 Antiviral activity against HIV-1 IIIB 35061384
Human immunodeficiency virus 1 EC50 = 14.0 nM 7.85 Antiviral activity against NNRTI-resistant HIV-1 harboring K103N mutant infected... 38613773
Human immunodeficiency virus 1 EC50 = 14.5 nM 7.84 Antiviral activity against HIV-1 IIIB harboring K103N/Y181C double mutant 35061384
Human immunodeficiency virus 1 EC50 = 15.0 nM 7.82 Antiviral activity against HIV1 RES056 containing reverse transcriptase K103N + ... 30606670
Human immunodeficiency virus 1 EC50 = 15.0 nM 7.82 Antiviral activity against HIV1 RES056 infected in human MT4 cells assessed as p... 34496571
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 19.0 nM 7.72 Inhibition of recombinant wild type HIV1 reverse transcriptase assessed as reduc... 30606670
Human immunodeficiency virus 1 EC50 = 25.0 nM 7.6 Antiviral activity against HIV-1 Y181C mutant infected in human MT4 cells assess... 35797898
Human immunodeficiency virus 1 EC50 = 27.0 nM 7.57 Antiviral activity against NNRTI-resistant HIV-1 harboring Y181C mutant infected... 38613773
Human immunodeficiency virus 1 EC50 = 37.0 nM 7.43 Antiviral activity against NNRTI-resistant HIV-1 harboring E138K mutant infected... 38613773
Human immunodeficiency virus 1 EC50 = 42.0 nM 7.38 Antiviral activity against HIV-1 K103N mutant infected in human MT4 cells assess... 35797898
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 44.0 nM 7.36 Inhibition of wild type HIV-1 Reverse transcriptase 35797898
Human immunodeficiency virus 1 EC50 = 128.0 nM 6.89 Antiviral activity against NNRTI-resistant HIV-1 harboring RES056 mutant infecte... 38613773

Literature References

PubMed DOI Target Context # Activities
24412110 10.1016/j.bmcl.2013.12.070 Human immunodeficiency virus 10
35797898 10.1016/j.ejmech.2022.114581 Human immunodeficiency virus 1 9
38613773 10.1021/acs.jmedchem.4c00026 Human immunodeficiency virus 1 8
24412110 10.1016/j.bmcl.2013.12.070 Canis familiaris 5
24412110 10.1016/j.bmcl.2013.12.070 Rattus norvegicus 5
24412110 10.1016/j.bmcl.2013.12.070 No relevant target 4
30606670 10.1016/j.bmc.2018.12.039 Unchecked 3
37393791 10.1016/j.ejmech.2023.115586 Human immunodeficiency virus 1 3
30606670 10.1016/j.bmc.2018.12.039 Human immunodeficiency virus 1 3
34496571 10.1021/acs.jmedchem.1c00987 Human immunodeficiency virus 1 2
34496571 10.1021/acs.jmedchem.1c00987 ADMET 2
35061384 10.1021/acs.jmedchem.1c01885 Human immunodeficiency virus 1 2
35061384 10.1021/acs.jmedchem.1c01885 ADMET 2
30606670 10.1016/j.bmc.2018.12.039 No relevant target 1
30606670 10.1016/j.bmc.2018.12.039 MT4 1
24412110 10.1016/j.bmcl.2013.12.070 Hepatocyte 1
30606670 10.1016/j.bmc.2018.12.039 Human immunodeficiency virus type 1 reverse transcriptase 1
30516990 10.1021/acs.jmedchem.8b00843 ADMET 1
34496571 10.1021/acs.jmedchem.1c00987 MT4 1
24412110 10.1016/j.bmcl.2013.12.070 Unchecked 1

Data from ChEMBL 36 via Core Engine