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Compound Detail

CHEMBL129

ZIDOVUDINE
💊 Approved Drug
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💊 Approved Drug
Cc1cn([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)c(=O)[nH]c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL129
Name ZIDOVUDINE
Phase Approved
Structure Type MOL
InChI Key HBOMLICNUCNMMY-XLPZGREQSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL193952

Known Names

3'-azt Azidothymidine AZT BW A509U BW-A-509U BW-A509U Bwa509u COMPOUND S COMPOUND-S NSC-602670 Retrovir Zidovudina +5 more
58
Targets
1,391
Activities
4
Assay Types
30
PK Parameters
20
Publications
17
Known Names
20
Indications
1
Mechanisms

Molecular Properties

267.2
MW (Da)
-0.20
ALogP
6
HBA
2
HBD
133.1
PSA (Ų)
0.45
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1987
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -vudine
USAN Year 1987

Extended Properties

Molecular Formula C10H13N5O4
MW 267.24
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 0.89

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

Autoimmune Diseases HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome AIDS Dementia Complex AIDS-Related Complex Diarrhea Pneumonia, Pneumocystis Pregnancy Severe Acute Respiratory Syndrome Tuberculosis Castleman Disease Infections Leukemia-Lymphoma, Adult T-Cell Liver Cirrhosis, Biliary Lymphoma Lymphoma, AIDS-Related Paraparesis, Tropical Spastic Sarcoma, Kaposi

ATC Classification

J05AF01
zidovudine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
metabolic toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
musculoskeletal toxicity
Country: United States

Activity Summary

EC50 959 meas. best 9.49
IC50 419 meas. best 9.85
Ki 11 meas. best 5.54
Kd 2 meas. best 8.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
PBMC
CHEMBL613107
 IC50 9.85 7.9975 0.1 4
Human immunodeficiency virus 2
CHEMBL380
 IC50 9.7 8.5057 0.2 7
Human immunodeficiency virus 1
CHEMBL378
 IC50 9.52 7.6194 0.3 128
CCRF-CEM
CHEMBL382
 EC50 9.49 8.2314 0.3 28
Simian immunodeficiency virus
CHEMBL613499
 IC50 9.3 8.65 0.5 2
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.28 7.7535 0.5 642
MT4
CHEMBL388
 EC50 9.15 8.0494 0.7 51
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 9.15 8.1213 0.7 15
B(EBV+)
CHEMBL614797
 EC50 9.0 9.0 1.0 1
ADMET
CHEMBL612558
 EC50 9.0 8.0483 1.0 29
ADMET
CHEMBL612558
 IC50 9.0 7.652 1.0 35
Human immunodeficiency virus 2
CHEMBL380
 EC50 8.8 7.7945 1.6 47
PBMC
CHEMBL613107
 EC50 8.74 8.38 1.8 5
CEM-SS
CHEMBL614548
 EC50 8.72 8.0364 1.9 11
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 8.7 8.0922 2.0 23
HeLa
CHEMBL399
 EC50 8.7 7.545 2.0 4
Human immunodeficiency virus
CHEMBL613758
 EC50 8.7 8.1143 2.0 21
Homo sapiens
CHEMBL372
 EC50 8.7 7.733 2.0 10
CEM-SS
CHEMBL614548
 IC50 8.7 7.9175 2.0 12
Human immunodeficiency virus
CHEMBL613758
 IC50 8.6 8.3 2.5 2
Unchecked
CHEMBL612545
 EC50 8.52 7.09 3.0 10
MT2
CHEMBL614184
 EC50 8.52 7.6017 3.0 6
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 8.52 6.7095 3.0 20
C8166
CHEMBL614533
 IC50 8.4 8.235 4.0 2
MT4
CHEMBL388
 IC50 8.4 6.2929 4.0 7
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Kd 8.27 8.27 5.4 1
MT2
CHEMBL614184
 IC50 8.22 5.9811 6.0 9
C8166
CHEMBL614533
 EC50 8.22 7.7436 6.0 11
CCRF-CEM
CHEMBL382
 IC50 8.22 5.6814 6.0 42
CEM-c113
CHEMBL614545
 EC50 8.22 8.22 6.0 1
Human immunodeficiency virus type 1 protease
CHEMBL243
 IC50 8.22 7.8867 6.0 3
MOLT-4
CHEMBL614177
 EC50 8.21 8.21 6.2 1
HIV-1 protease
CHEMBL4296312
 EC50 8.15 8.15 7.0 1
H9
CHEMBL614806
 EC50 8.05 7.3406 9.0 18
Jurkat
CHEMBL397
 IC50 8.0 8.0 10.0 1
Unchecked
CHEMBL612545
 IC50 8.0 6.2609 10.0 11
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.96 6.725 11.0 6
Simian immunodeficiency virus
CHEMBL613499
 EC50 7.96 7.935 11.0 2
M
CHEMBL614115
 EC50 7.82 7.82 15.0 1
C3H/3T3
CHEMBL614372
 EC50 7.7 7.7 20.0 1
Homo sapiens
CHEMBL372
 IC50 7.7 7.05 20.0 2
Rauscher murine leukemia virus
CHEMBL613748
 IC50 7.64 7.64 23.0 1
Porcine endogenous retrovirus
CHEMBL613016
 EC50 7.64 7.64 23.0 1
PBL
CHEMBL614233
 EC50 7.54 7.54 29.0 1
U-937
CHEMBL612794
 EC50 7.52 7.52 30.0 1
H9
CHEMBL614806
 IC50 7.52 7.3267 30.0 3
Mus musculus
CHEMBL375
 EC50 7.46 7.4 35.0 2
U-937
CHEMBL612794
 IC50 7.4 7.4 40.0 1
Human immunodeficiency virus 3
CHEMBL612359
 EC50 7.4 7.4 40.0 1
SUP-T1
CHEMBL614940
 IC50 7.3 7.3 50.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 26640.0 ng.hr.mL-1 -
AUC 1210.0 ng.hr.mL-1 -
AUC 25380.0 ng.hr.mL-1 -
AUC 11280.0 ng.hr.mL-1 -
AUC 11785000.0 ng.hr.mL-1 Mus musculus
AUC 174700.0 ng.hr.mL-1 -
AUC 11883.0 fmol Homo sapiens
AUC 627.0 fmol Homo sapiens
AUC 502.0 fmol Homo sapiens
AUC 0.85 fmol Homo sapiens
AUC 9.62 ng.hr/ml/mg Homo sapiens
AUC 6.51 ng.hr/ml/mg Homo sapiens
AUC 8.77 ng.hr/ml/mg Homo sapiens
CL 12.4 mL.min-1.kg-1 Homo sapiens
CL 25.0 mL.min-1.kg-1 Homo sapiens
CL 46.0 mL.min-1.kg-1 Rattus norvegicus
CL 14.0 mL.min-1.kg-1 Canis lupus familiaris
CL 15.0 mL.min-1.kg-1 Macaca
CL 24.0 mL.min-1.kg-1 Homo sapiens
CL 25.0 mL.min-1.kg-1 Homo sapiens
CL 33.3 mL.min-1.kg-1 Homo sapiens
CL 25.0 mL.min-1.kg-1 Homo sapiens
Cmax 0.002998 nM Homo sapiens
Cmax 6.247e-05 nM Homo sapiens
Cmax 4.39e-05 nM Homo sapiens
Cmax 7.58 ng/ml/mg Homo sapiens
Cmax 4.34 ng/ml/mg Homo sapiens
Cmax 6.74 ng/ml/mg Homo sapiens
Cmax 4.34 ng/ml/mg Homo sapiens
F 79.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
PBMC IC50 = 0.14 nM 9.85 Antiviral activity against HIV1 TEKI replication in PBMC at 1 uM 16420027
PBMC IC50 = 0.18 nM 9.74 Antiviral activity against HIV1 NL4-3 replication in PBMC at 1 uM 16420027
Human immunodeficiency virus 2 IC50 = 0.2 nM 9.7 Antiviral activity against Human immunodeficiency virus 2 CDC 310319 infected in... 20086149
Human immunodeficiency virus 1 IC50 = 0.3 nM 9.52 Antiviral activity against Human immunodeficiency virus 1 subtype F BR/93/020 in... 20086149
Human immunodeficiency virus 1 IC50 = 0.3 nM 9.52 Antiviral activity against of Human immunodeficiency virus 1 3B infected in AA5 ... 20086149
CCRF-CEM EC50 = 0.32 nM 9.49 Concentration of the drug resulting in 50% reduction of the viral cytopathic eff... 2153206
Human immunodeficiency virus 1 IC50 = 0.4 nM 9.4 Antiviral activity against of Human immunodeficiency virus 1 3B infected in AA5 ... 20086149
Human immunodeficiency virus 1 IC50 = 0.5 nM 9.3 Antiviral activity against Human immunodeficiency virus 1 subtype O BCF02 infect... 20086149
Simian immunodeficiency virus IC50 = 0.5 nM 9.3 Antiviral activity against simian immunodeficiency virus 69R infected in phytohe... 20086149
Human immunodeficiency virus 1 EC50 = 0.53 nM 9.28 Antiviral activity against HIV1 NL 4-3 expressing wild type reverse transcriptas... 20439609
Human immunodeficiency virus 1 IC50 = 0.7 nM 9.15 Antiviral activity against Human immunodeficiency virus 1 subtype D UG/92/046 in... 20086149
Human immunodeficiency virus 1 EC50 = 0.7 nM 9.15 Antiviral activity against HIV1 3B assessed as inhibition of virus-induced cytop... 17964796
MT4 EC50 = 0.7 nM 9.15 Dose required to achieve 50% protection of MT-4 cells from HIV-1(IIIB) induced c... 9767646
NON-PROTEIN TARGET EC50 = 0.7 nM 9.15 In vitro effective concentration against HIV-1 cytopathic effect in T4 cells 10956199
Human immunodeficiency virus 1 EC50 = 0.73 nM 9.14 Antiviral activity against HIV1 LAI replication in human PBMC after 5 days 17158051
Human immunodeficiency virus 1 IC50 = 0.8 nM 9.1 Antiviral activity against Human immunodeficiency virus 1 subtype A RW/92/016 in... 20086149
Human immunodeficiency virus 1 IC50 = 0.8 nM 9.1 Antiviral activity against HIV1 NL43 infected din human MT4 cells pre-incubated ... 22858300
Human immunodeficiency virus 1 EC50 = 0.8 nM 9.1 Antiviral activity against HIV1 in MT4 cells 17188402
Human immunodeficiency virus 1 EC50 = 0.96 nM 9.02 Antiviral activity against HIV1 JRCSF infected in human PBMC assessed as inhibit... 19451305
ADMET IC50 = 1.0 nM 9.0 Antiviral activity against subtype isolate O strain in PBLs (peripheral blood ly... 11708913

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 301
20439609 10.1128/aac.00068-10 Human immunodeficiency virus 1 110
- 10.5281/zenodo.13943903 ADMET 87
1712047 10.1021/jm00110a011 Human immunodeficiency virus type 1 reverse transcriptase 64
1501232 10.1021/jm00094a018 Mus musculus 45
18316521 10.1128/aac.01313-07 Human immunodeficiency virus 1 43
20086149 10.1128/aac.01443-09 Human immunodeficiency virus 1 40
11708913 10.1021/jm010212m ADMET 28
20194692 10.1128/aac.00870-09 Human immunodeficiency virus 1 24
8632406 10.1021/jm9408326 Mus musculus 24
17664328 10.1128/aac.01626-06 Homo sapiens 23
- 10.1016/S0960-894X(00)80410-2 ADMET 22
19596885 10.1128/aac.00392-09 Human immunodeficiency virus 1 21
17724147 10.1128/aac.00692-07 CCRF-CEM 19
20038617 10.1128/aac.01209-09 Homo sapiens 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
17158934 10.1128/aac.01078-06 Rattus norvegicus 17
18955518 10.1128/aac.00689-08 Human immunodeficiency virus 1 16
7932526 10.1021/jm00045a008 Human immunodeficiency virus 16
21123165 10.1124/dmd.110.036608 UDP-glucuronosyltransferase 2B7 16

Data from ChEMBL 36 via Core Engine