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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View more information in the IUPHAR Pharmacology Education Project: zidovudine

2D Structure
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Physico-chemical Properties
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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
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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
1. Baldwin SA, Yao SY, Hyde RJ, Ng AM, Foppolo S, Barnes K, Ritzel MW, Cass CE, Young JD. (2005)
Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes.
J Biol Chem, 280 (16): 15880-7. [PMID:15701636]