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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL129
CHEMBL129
Compound Name ZIDOVUDINE
ChEMBL Synonyms RETROVIR | ZIDOVUDINE | BWA509U | BW A509U | COMPOUND S | BW-A-509U | Azidothymidine | AZT
Max Phase 4 (Approved)
Trade Names AZT | Azidothymidine | RETROVIR | ZIDOVUDINE
Molecular Formula C10H13N5O4

Additional synonyms for CHEMBL129 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O
Standard InChI InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11 ...
Download InChI
Standard InChI Key HBOMLICNUCNMMY-XLPZGREQSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL129

Molecule Features

CHEMBL129 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:Y Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Human immunodeficiency virus type 1 reverse transcriptase inhibitor Human immunodeficiency virus type 1 reverse transcriptase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
InfectionD007239EFO:0000544infection2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma2ClinicalTrials
AIDS Dementia ComplexD015526EFO:0002608AIDS dementia3ClinicalTrials
Castleman DiseaseD005871EFO:1001332Giant Lymph Node Hyperplasia2ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000209T-cell acute lymphoblastic leukemia2ClinicalTrials
Acquired Immunodeficiency SyndromeD000163EFO:0000765AIDS3ClinicalTrials
Amyotrophic Lateral SclerosisD000690EFO:0000253amyotrophic lateral sclerosis1ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection4ClinicalTrials
DailyMed
Liver Cirrhosis, BiliaryD008105EFO:1001486primary biliary cirrhosis2ClinicalTrials
Paraparesis, Tropical SpasticD015493EFO:0007527tropical spastic paraparesis2ClinicalTrials
Severe Combined ImmunodeficiencyD016511Orphanet:183660Severe combined immunodeficiency1ClinicalTrials
AIDS-Related ComplexD000386EFO:0007137AIDS related complex3ClinicalTrials
DiarrheaD003967HP:0002014diarrhea3ClinicalTrials
Lymphoma, AIDS-RelatedD016483EFO:1001365Lymphoma, AIDS-Related2ClinicalTrials
Sarcoma, KaposiD012514EFO:0000558Kaposi's sarcoma2ClinicalTrials
HIV InfectionsD015658EFO:0000180HIV-1 infection4ClinicalTrials

Clinical Data

ClinicalTrials.gov ZIDOVUDINE
The Cochrane Collaboration ZIDOVUDINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL129. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 1.000
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 1.000
CHEMBL3415 Thymidine kinase Human herpesvirus 2 1.000
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 1.000
CHEMBL2366516 Reverse transcriptase Human immunodeficiency virus 1 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 1.000
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 1.000
CHEMBL2361 Thymidylate kinase Mycobacterium tuberculosis 1.000
CHEMBL2123 Pyrimidinergic receptor P2Y4 Homo sapiens 0.990
CHEMBL2304404 Adenosine A1 receptor Cavia porcellus 0.410



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2883 Thymidine kinase, cytosolic Homo sapiens 1.000
CHEMBL1820 Thymidine kinase Human herpesvirus 1 (strain SC16) (HHV-1) (Human herpes simplex virus1) 1.000
CHEMBL2361 Thymidylate kinase Mycobacterium tuberculosis 1.000
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL4580 Thymidine kinase, mitochondrial Homo sapiens 1.000
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 1.000
CHEMBL3106 Thymidine phosphorylase Homo sapiens 1.000
CHEMBL3415 Thymidine kinase Human herpesvirus 2 1.000
CHEMBL1795127 Thymidine kinase Human herpesvirus 1 1.000
CHEMBL2366516 Reverse transcriptase Human immunodeficiency virus 1 1.000
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 1.000
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 1.000
CHEMBL2123 Pyrimidinergic receptor P2Y4 Homo sapiens 1.000
CHEMBL1828 DNA polymerase alpha subunit Homo sapiens 1.000
CHEMBL4518 Purinergic receptor P2Y14 Homo sapiens 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.940
CHEMBL4696 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 0.655
CHEMBL2966 Adenosine deaminase Bos taurus 0.251

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
267.3 267.0968 -0.2 3 133.08 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 2 0 9 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.55 - .05 .05 1 19 0.45

Structural Alerts

There are 8 structural alerts for CHEMBL129. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J05 - ANTIVIRALS FOR SYSTEMIC USE
J05A - DIRECT ACTING ANTIVIRALS
J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors
J05AF01 - zidovudine

ChemSpider ChemSpider:HBOMLICNUCNMMY-XLPZGREQSA-N
DailyMed zidovudine
PubChem SID: 144203613 SID: 144204445 SID: 144209401 SID: 144210895 SID: 170464737 SID: 17390027 SID: 26751584 SID: 49718184 SID: 855980 SID: 90341185
Wikipedia Zidovudine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL129



ACToR 30516-87-1
BindingDB 50002692
Brenda 4954 210376 23308 29429 19716 1185
ChEBI 10110
DrugBank DB00495
DrugCentral 2861
eMolecules 479032 747869
EPA CompTox Dashboard DTXSID8020127
FDA SRS 4B9XT59T7S
Guide to Pharmacology 4825
Human Metabolome Database HMDB0014638
IBM Patent System 2271078CEF6FACCDC555BC469AD12106
KEGG Ligand C07210
LINCS LSM-5806
Mcule MCULE-8664408343
MolPort MolPort-002-507-286
NIH Clinical Collection SAM002548971
Nikkaji J20.566D
PDBe AZZ
PharmGKB PA451954
PubChem 35370
PubChem: Drugs of the Future 12013681
PubChem: Thomson Pharma 15221752 14799161
Selleck zidovudine-retrovir
SureChEMBL SCHEMBL7409
ZINC ZINC000003779042

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/HBOMLICNUCNMMY-XLPZGREQSA-N spacer
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