zidovudine   Click here for help

GtoPdb Ligand ID: 4825

Abbreviated name: AZT
Synonyms: 3'-azido-3'-deoxythymidine | Retrovir®
Approved drug PDB Ligand
zidovudine is an approved drug (FDA (1987))
Compound class: Synthetic organic
Comment: Zidovudine (AZT) is a nucleoside analogue reverse-transcriptase inhibitor (NRTI) class antiretroviral drug. It was the first antiretroviral for HIV to be approved by the US FDA, and it is now listed in the World Health Organization's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 96.68
Molecular weight 267.1
XLogP -0.12
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCC1OC(CC1N=[N+]=[N-])n1cc(C)c(=O)[nH]c1=O
Isomeric SMILES OC[C@H]1O[C@H](C[C@@H]1N=[N+]=[N-])n1cc(C)c(=O)[nH]c1=O
InChI InChI=1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1
InChI Key HBOMLICNUCNMMY-XLPZGREQSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1987))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
6118 zidovudine
Synonyms Click here for help
3'-azido-3'-deoxythymidine | Retrovir®
Database Links Click here for help
CAS Registry No. 30516-87-1 (source: Scifinder)
ChEBI CHEBI:10110
ChEMBL Ligand CHEMBL129
DrugBank Ligand DB00495
DrugCentral Ligand 2861
GtoPdb PubChem SID 178101527
Immunopaedia Search zidovudine
PubChem CID 35370
RCSB PDB Ligand AZZ
Search Google for chemical match using the InChIKey HBOMLICNUCNMMY-XLPZGREQSA-N
Search Google for chemicals with the same backbone HBOMLICNUCNMMY
Search PubMed clinical trials zidovudine
Search PubMed titles zidovudine
Search PubMed titles/abstracts zidovudine
UniChem Compound Search for chemical match using the InChIKey HBOMLICNUCNMMY-XLPZGREQSA-N
UniChem Connectivity Search for chemical match using the InChIKey HBOMLICNUCNMMY-XLPZGREQSA-N
Wikipedia Zidovudine

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Tocris
Azidothymidine (links to external site)
Cat. No. 4150