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Compound Detail

CHEMBL1163

ATAZANAVIR
💊 Approved Drug
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💊 Approved Drug
COC(=O)N[C@H](C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(Cc1ccc(-c2ccccn2)cc1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C(C)(C)C

Basic Information

ChEMBL ID CHEMBL1163
Name ATAZANAVIR
Phase Approved
Structure Type MOL
InChI Key AXRYRYVKAWYZBR-GASGPIRDSA-N
Therapeutic ✓ Yes

Known Names

Atazanavir BMS-232632 CGP-73547 Reyataz
23
Targets
248
Activities
4
Assay Types
30
PK Parameters
20
Publications
4
Known Names
7
Indications

Molecular Properties

704.9
MW (Da)
4.21
ALogP
9
HBA
5
HBD
171.2
PSA (Ų)
0.15
QED
1
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2003
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -vir
USAN Year 2002

Extended Properties

Molecular Formula C38H52N6O7
MW 704.87
Aromatic Rings 3
Heavy Atoms 51
NP-Likeness -0.15

Indications

Virus Diseases Acquired Immunodeficiency Syndrome HIV Infections HIV Infections Severe Acute Respiratory Syndrome Diabetes Mellitus, Type 1 Hematologic Neoplasms

ATC Classification

J05AE08
atazanavir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 132 meas. best 9.15
IC50 82 meas. best 10.4
Ki 33 meas. best 10.62
Kd 1 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protease
CHEMBL2366517
Ki 10.62 9.5825 0.0 8
Protease
CHEMBL2366517
IC50 10.4 9.2533 0.0 6
Human immunodeficiency virus type 1 protease
CHEMBL243
Ki 10.27 9.715 0.1 8
Unchecked
CHEMBL612545
Ki 9.48 8.1617 0.3 12
Human immunodeficiency virus type 1 protease
CHEMBL243
Kd 9.4 9.4 0.4 1
Human immunodeficiency virus 1
CHEMBL378
EC50 9.15 7.5009 0.7 120
Protease
CHEMBL2366517
EC50 9.15 9.15 0.7 1
Human immunodeficiency virus 1
CHEMBL378
IC50 9.05 7.1953 0.9 30
Human immunodeficiency virus 2
CHEMBL380
EC50 8.52 7.8056 3.0 9
Unchecked
CHEMBL612545
IC50 8.4 7.28 4.0 2
Human immunodeficiency virus type 1 protease
CHEMBL243
IC50 8.4 8.4 4.0 1
HIV-1 protease
CHEMBL4296312
IC50 8.16 8.16 6.9 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 8.15 6.24 7.0 2
Human immunodeficiency virus
CHEMBL613758
IC50 7.6 7.2633 25.0 3
MT4
CHEMBL388
IC50 7.6 7.2633 25.0 3
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
IC50 7.58 7.58 26.0 1
Human immunodeficiency virus 2
CHEMBL380
IC50 7.52 6.8856 30.0 18
UDP-glucuronosyltransferase 1A1
CHEMBL1287617
IC50 6.52 6.37 300.0 4
SARS-CoV-2
CHEMBL4303835
EC50 6.5 6.1 320.0 2
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
Ki 6.43 6.43 370.0 1
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
IC50 6.4 6.4 400.0 1
Replicase polyprotein 1ab
CHEMBL4523582
Ki 6.15 6.15 703.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
Ki 5.89 5.89 1300.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 5.85 5.85 1400.0 1
UDP-glucuronosyltransferase 1A1
CHEMBL4523339
IC50 5.47 5.425 3400.0 2
Solute carrier organic anion transporter family member 2B1
CHEMBL1743124
Ki 5.29 5.29 5100.0 1
Solute carrier organic anion transporter family member 2B1
CHEMBL1743124
IC50 5.28 5.28 5200.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.1 5.1 7950.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 4.89 4.89 12740.0 1
Leishmania donovani
CHEMBL367
IC50 4.62 4.62 24100.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.48 4.48 33340.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
IC50 4.17 4.17 67800.0 1
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
IC50 4.16 4.16 69100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 10573.05 ng.hr.mL-1 Canis lupus familiaris
AUC 23800.0 ng.hr.mL-1 Homo sapiens
AUC 5100.0 ng.hr.mL-1 Homo sapiens
AUC 9800.0 ng.hr.mL-1 Homo sapiens
AUC 47600.0 ng.hr.mL-1 Homo sapiens
AUC 10300.0 ng.hr.mL-1 Homo sapiens
AUC 19600.0 ng.hr.mL-1 Homo sapiens
AUC 29303.0 ng.hr.mL-1 Homo sapiens
AUC 61435.0 ng.hr.mL-1 Homo sapiens
AUC 47410.0 ng.hr.mL-1 Homo sapiens
AUC 35432.0 ng.hr.mL-1 Homo sapiens
AUC 49644.0 ng.hr.mL-1 Homo sapiens
AUC 36529.0 ng.hr.mL-1 Homo sapiens
AUC 53500.0 ng.hr.mL-1 Homo sapiens
AUC 33100.0 ng.hr.mL-1 Homo sapiens
AUC 33500.0 ng.hr.mL-1 Homo sapiens
AUC 26412.0 ng.hr.mL-1 Homo sapiens
AUC 30329.0 ng.hr.mL-1 Homo sapiens
AUC 270.67 ng.hr.mL-1 Rattus norvegicus
AUC 3.524 ng.hr.mL-1 Rattus norvegicus
AUC 1733.98 ng.hr.mL-1 Rattus norvegicus
AUC 169.17 ng.hr.mL-1 Rattus norvegicus
AUC 270.67 ng.hr.mL-1 Rattus norvegicus
AUC 270.67 ng.hr.mL-1 Rattus norvegicus
AUC 14696.54 ng.hr.mL-1 Rattus norvegicus
AUC 270.67 ng.hr.mL-1 Rattus norvegicus
AUC 14696.54 ng.hr.mL-1 Rattus norvegicus
AUC 448.3 ng.hr.mL-1 Rattus norvegicus
CL 26.67 mL.min-1.kg-1 Canis lupus familiaris
CL 90.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protease Ki = 0.024 nM 10.62 Inhibition of wild-type HIV1 BH10 protease expressed in Escherichia coli by spec... 18598016
Protease Ki = 0.039 nM 10.41 Inhibition of HIV1 protease 17638694
Protease IC50 = 0.04 nM 10.4 Inhibition of HIV1 protease expressed in Escherichia coli using Val-Ser-Gln-Asn-... 29259750
Protease IC50 = 0.04 nM 10.4 Inhibition of wild-type HIV1 protease expressed in Escherichia coli assessed as ... 27437081
Protease Ki = 0.0479 nM 10.32 Inhibition of HIV1 protease using fluorogenic hexapeptide substrate (2-aminobenz... -
Protease Ki = 0.05 nM 10.3 Inhibition of HIV1 protease 17981045
Human immunodeficiency virus type 1 protease Ki = 0.054 nM 10.27 Inhibition of HIV1 recombinant protease L10F/L19I/K20R/L33F/E35D/M36I/R41K/F53L/... 18598016
Human immunodeficiency virus type 1 protease Ki = 0.055 nM 10.26 Inhibition of HIV1 recombinant protease D30N/N88D mutant expressed in Escherichi... 18598016
Human immunodeficiency virus type 1 protease Ki = 0.076 nM 10.12 Inhibition of HIV1 recombinant protease L10I/I15V/E35D/N37S/R41K/I62V/L63P/A71V/... 18598016
Human immunodeficiency virus type 1 protease Ki = 0.17 nM 9.77 Inhibition of HIV1 recombinant protease V32I/I47A mutant expressed in Escherichi... 18598016
Human immunodeficiency virus type 1 protease Ki = 0.23 nM 9.64 Inhibition of HIV1 recombinant protease A71V/V82T/I84V mutant expressed in Esche... 18598016
Human immunodeficiency virus type 1 protease Ki = 0.24 nM 9.62 Inhibition constant for human immunodeficiency virus type 1 protease 15537350
Protease IC50 = 0.3 nM 9.52 Inhibition of HIV1 protease activity 30938524
Unchecked Ki = 0.33 nM 9.48 Inhibition of HIV1 Protease M1 variant by FRET based assay 17696512
Human immunodeficiency virus type 1 protease Kd = 0.4 nM 9.4 Binding affinity for human immunodeficiency virus type 1 protease 15537350
Unchecked Ki = 0.49 nM 9.31 Inhibition of HIV1 Protease M3 variant by FRET based assay 17696512
Protease Ki = 0.5 nM 9.3 Inhibition of HIV1 protease expressed in Escherichia coli by fluorometric assay 19961222
Human immunodeficiency virus 1 EC50 = 0.7 nM 9.15 Antiviral activity against HIV1 NL4-3 infected in human MT2 cells assessed as re... 30938524
Protease EC50 = 0.7 nM 9.15 Inhibition of HIV1 NL4-3 protease assessed as decrease in viral replication in h... 29693401
Human immunodeficiency virus type 1 protease Ki = 0.76 nM 9.12 Inhibition of HIV1 recombinant protease M46I/A71V/V82T/I84V mutant expressed in ... 18598016

Literature References

PubMed DOI Target Context # Activities
17638694 10.1128/aac.00149-07 Human immunodeficiency virus 1 53
17576825 10.1128/aac.00341-07 Homo sapiens 46
18227188 10.1128/aac.01284-07 Human immunodeficiency virus 2 36
20308382 10.1128/aac.01784-09 Human immunodeficiency virus 1 31
18212102 10.1128/aac.01132-07 Human immunodeficiency virus 1 29
17101675 10.1128/aac.00690-06 Human immunodeficiency virus 1 26
17371811 10.1128/aac.01413-06 Human immunodeficiency virus 1 24
17981045 10.1016/j.bmc.2007.10.062 Human immunodeficiency virus 1 17
18955518 10.1128/aac.00689-08 Human immunodeficiency virus 1 17
26799988 10.1021/acs.jmedchem.5b01697 Human immunodeficiency virus 1 17
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 1 17
30938524 10.1021/acs.jmedchem.9b00002 ADMET 17
35952307 10.1021/acs.jmedchem.2c00632 ADMET 16
30938524 10.1021/acs.jmedchem.9b00002 No relevant target 16
28418652 10.1021/acs.jmedchem.7b00172 Human immunodeficiency virus 1 15
21148252 10.1124/dmd.110.036327 ADMET 14
19995932 10.1128/aac.00797-09 Homo sapiens 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20404123 10.1128/aac.01828-09 Human immunodeficiency virus 1 12
18573930 10.1128/aac.00194-08 Homo sapiens 12

Data from ChEMBL 36 via Core Engine