Compound ID | 3505

Update compound information

Zidovudine

Synonym(s): AZT  |  BW A509U

Class: DNA synthesis inhibitor

Spectrum of activity: Gram-negative
Details of activity: Active against Enterobacteriales; likely DNA synthesis inhibitor (potentially phosphorylated by thymidine kinases which acts as DNA chain terminator when incorporated into DNA) and sensitizer
Description: Synthetic compound; a repurposed FDA-approved drug targeting HIV reverse transcriptase inhibitor; shows synergistic effect with nitrofuran, tetracyclines, and quinolones; shows modest antibacterial effect on its own (MIC 4 mg/L) but acts as sensitiser
Year first mentioned: 1990
Development status: Experimental
Chemical structure(s):
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Molecular weight: 267.24
Iso. SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
InChI Key: HBOMLICNUCNMMY-XLPZGREQSA-N
Can. SMILES: CC1=CN([C@H]2C[C@@H]([C@@H](CO)O2)N=[N+]=[N-])C(=O)NC1=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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/35370
Citations:
  • https://academic.oup.com/jac/article/25/4/706/731891?login=true
  • https://pubmed.ncbi.nlm.nih.gov/3551832/
  • https://journals.asm.org/doi/10.1128/aac.00344-24

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