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Compound Detail

CHEMBL1323

DARUNAVIR
💊 Approved Drug
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💊 Approved Drug
CC(C)CN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@H]2OCC[C@H]21)S(=O)(=O)c1ccc(N)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1323
Name DARUNAVIR
Phase Approved
Structure Type MOL
InChI Key CJBJHOAVZSMMDJ-HEXNFIEUSA-N
Therapeutic ✓ Yes

Known Names

(-)-darunavir Darunavir Darunavir component of prezcobix Darunavir component of symtuza Darunavir krka Darunavir krka d.d. Darunavir viatris (previously darunavir mylan) Prezista TMC 114 TMC-114 TMC-41629 TMC114 +2 more
18
Targets
450
Activities
4
Assay Types
16
PK Parameters
20
Publications
14
Known Names
10
Indications
1
Mechanisms

Molecular Properties

547.7
MW (Da)
2.38
ALogP
8
HBA
3
HBD
140.4
PSA (Ų)
0.36
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2006
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -vir
USAN Year 2005

Extended Properties

Molecular Formula C27H37N3O7S
MW 547.67
Aromatic Rings 2
Heavy Atoms 38
NP-Likeness 0.12

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human immunodeficiency virus type 1 protease inhibitor INHIBITOR Human immunodeficiency virus type 1 protease ✓ ✓

Indications

HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome Infections Pneumonia, Pneumocystis Severe Acute Respiratory Syndrome Amyotrophic Lateral Sclerosis Hepatitis C Insulin Resistance

ATC Classification

J05AE10
darunavir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 205 meas. best 9.82
IC50 149 meas. best 10.89
Ki 93 meas. best 11.0
Kd 3 meas. best 10.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protease
CHEMBL2366517
 Ki 11.0 10.2426 0.0 34
Human immunodeficiency virus type 1 protease
CHEMBL243
 Ki 11.0 9.51 0.0 26
Protease
CHEMBL2366517
 IC50 10.89 9.49 0.0 7
Unchecked
CHEMBL612545
 Ki 10.82 8.92 0.0 17
Protease
CHEMBL2366517
 Kd 10.8 10.8 0.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.82 7.7449 0.1 189
Human immunodeficiency virus type 1 protease
CHEMBL243
 IC50 9.29 8.2088 0.5 8
Human immunodeficiency virus 1
CHEMBL378
 IC50 9.09 7.8942 0.8 91
HIV-1 protease
CHEMBL4296312
 IC50 8.82 8.82 1.5 1
Human immunodeficiency virus
CHEMBL613758
 IC50 8.8 8.74 1.6 2
Human immunodeficiency virus 2
CHEMBL380
 IC50 8.7 7.3044 2.0 18
MT4
CHEMBL388
 IC50 8.41 8.0267 3.9 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.4 8.4 4.0 1
Human immunodeficiency virus 2
CHEMBL380
 EC50 8.22 7.863 6.0 10
Protease
CHEMBL2366517
 EC50 7.9 7.425 12.7 2
Unchecked
CHEMBL612545
 Kd 7.39 7.39 41.0 1
Homo sapiens
CHEMBL372
 EC50 6.16 5.535 700.0 2
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.18 4.6725 6600.0 4
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.5 4.5 31410.0 1
Sodium channel protein type 5 subunit alpha
CHEMBL1980
 IC50 4.4 4.2 39810.7 2
Plasmodium falciparum
CHEMBL364
 IC50 4.33 4.33 46930.0 1
Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK)
CHEMBL2221347
 IC50 4.3 4.3 50118.7 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.2 4.1 63095.7 2
Plasmodium falciparum
CHEMBL364
 EC50 4.16 4.16 70000.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.04 4.04 92210.0 1
A-type voltage-gated potassium channel KCND3
CHEMBL1964
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1474.0 ng.hr.mL-1 Rattus norvegicus
AUC 1578.5 ng.hr.mL-1 Rattus norvegicus
AUC 74081.0 ng.hr.mL-1 Canis lupus familiaris
CL 30.9 mL.min-1.g-1 Homo sapiens
CL 1.6 mL.min-1.g-1 Homo sapiens
CL 0.9 mL.min-1.g-1 Homo sapiens
Cmax 1300.05 nM Rattus norvegicus
Cmax 34875.02 nM Canis lupus familiaris
Cmax 1823.18 nM Rattus norvegicus
T1/2 6.04 hr Rattus norvegicus
T1/2 2.06 hr Rattus norvegicus
T1/2 0.781 hr Canis lupus familiaris
T1/2 0.06 hr Homo sapiens
Tmax 0.5 hr Rattus norvegicus
Tmax 1.0 hr Rattus norvegicus
Tmax 1.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protease Ki = 0.01 nM 11.0 Inhibition of HIV1 protease using RE(Edans)SGIFLETSK(Dabcyl)R as substrate by fl... 31050421
Human immunodeficiency virus type 1 protease Ki = 0.01 nM 11.0 Inhibition of HIV-1 protease by fluorescence assay 36793428
Human immunodeficiency virus type 1 protease Ki = 0.011 nM 10.96 Inhibition of HIV1 recombinant protease D30N/N88D mutant expressed in Escherichi... 18598016
Protease IC50 = 0.013 nM 10.89 Inhibition of HIV1 protease expressed in Escherichia coli using Val-Ser-Gln-Asn-... 29259750
Human immunodeficiency virus type 1 protease Ki = 0.014 nM 10.85 Inhibition of HIV1 protease 16913714
Protease Ki = 0.014 nM 10.85 Inhibition of HIV1 protease 19323561
Human immunodeficiency virus type 1 protease Ki = 0.015 nM 10.82 Inhibitory activity against human immunodeficiency virus 1 protease 15887965
Human immunodeficiency virus type 1 protease Ki = 0.015 nM 10.82 Inhibition of HIV1 recombinant protease L10I/I15V/E35D/N37S/R41K/I62V/L63P/A71V/... 18598016
Unchecked Ki = 0.015 nM 10.82 Inhibition of HIV protease 21381769
Protease Ki = 0.016 nM 10.8 Inhibition of HIV1 protease 26306007
Human immunodeficiency virus type 1 protease Ki = 0.016 nM 10.8 Inhibition of HIV-1 protease expressed in Escherichia coli assessed as inhibitio... 37150084
Human immunodeficiency virus type 1 protease Ki = 0.016 nM 10.8 Inhibition of HIV-1 protease using Abz-NF-6 as substrate assessed as inhibition ... 36738797
Protease Ki = 0.016 nM 10.8 Inhibition of HIV-1 protease 32348139
Protease Ki = 0.016 nM 10.8 Inhibition of HIV1 protease using Ac-Thr-Ile-Nle-Nle-Gln-Arg-NH2 substrate by co... 31416666
Protease Ki = 0.016 nM 10.8 Inhibition of HIV1 wild type NL4-3 protease expressed in Escherichia coli Rosett... 30354121
Protease Ki = 0.016 nM 10.8 Inhibition of wild type HIV-1 NL4-3 protease expressed in Escherichia coli Roset... 29763303
Unchecked Ki = 0.016 nM 10.8 Inhibition of wild-type HIV-1 protease 28958624
Unchecked Ki = 0.016 nM 10.8 Inhibition of HIV-1 protease using fluorogenic substrate by fluorescence assay 28958624
Unchecked Ki = 0.016 nM 10.8 Inhibition of HIV1 protease using fluorogenic substrate by continuous fluorometr... 28434781
Protease Ki = 0.016 nM 10.8 Inhibition of HIV1 protease 17900913

Literature References

PubMed DOI Target Context # Activities
18227188 10.1128/aac.01284-07 Human immunodeficiency virus 2 36
26799988 10.1021/acs.jmedchem.5b01697 Human immunodeficiency virus 1 32
17371811 10.1128/aac.01413-06 Human immunodeficiency virus 1 24
28418652 10.1021/acs.jmedchem.7b00172 Human immunodeficiency virus 1 22
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 1 19
37244161 10.1016/j.ejmech.2023.115501 Human immunodeficiency virus 1 18
17620375 10.1128/aac.00401-07 Human immunodeficiency virus 1 18
18955518 10.1128/aac.00689-08 Human immunodeficiency virus 1 16
15771427 10.1021/jm049560p ADMET 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19746963 10.1021/jm900695w Human immunodeficiency virus 1 14
15771427 10.1021/jm049560p Human immunodeficiency virus 1 13
18212102 10.1128/aac.01132-07 Human immunodeficiency virus 1 12
20034787 10.1016/j.bmcl.2009.11.123 Human immunodeficiency virus 1 12
26509831 10.1021/acs.jmedchem.5b00497 Protease 11
21800876 10.1021/jm200649p Human immunodeficiency virus 1 10
18783203 10.1021/jm8004543 Human immunodeficiency virus 1 10
17576848 10.1128/aac.00146-07 Human immunodeficiency virus 2 10
22749283 10.1016/j.bmcl.2012.05.120 Human immunodeficiency virus 1 9
22364812 10.1016/j.bmcl.2012.01.061 Human immunodeficiency virus 1 9

Data from ChEMBL 36 via Core Engine