Zidovudine

"AZT" redirects here. For other uses, see AZT (disambiguation).

Zidovudine
Clinical data
Trade namesRetrovir, others
AHFS/Drugs.comMonograph
MedlinePlusa687007
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, intravenous, rectal suppository
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityComplete absorption, following first-pass metabolism systemic availability 75% (range 52 to 75%)
Protein binding30 to 38%
MetabolismLiver
Elimination half-life0.5 to 3 hours
ExcretionKidney and Bile duct
Identifiers
  • 3'-deoxy-3'-azido-thymidine
    1-[(2R,4S,5S)-4-Azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione[5]
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.152.492 Edit this at Wikidata
Chemical and physical data
FormulaC10H13N5O4
Molar mass267.245 g·mol−1
3D model (JSmol)
  • O=C1NC(C(C)=CN1[C@@H]2O[C@H](CO)[C@@H](N=[N+]=[N-])C2)=O
  • 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 checkY
  • Key:HBOMLICNUCNMMY-XLPZGREQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Zidovudine (ZDV), also known as azidothymidine (AZT), was the first antiretroviral medication used to prevent and treat HIV/AIDS. It is generally recommended for use in combination with other antiretrovirals.[6] It may be used to prevent mother-to-child spread during birth or after a needlestick injury or other potential exposure.[6] It is sold both by itself and together as lamivudine/zidovudine and abacavir/lamivudine/zidovudine.[6] It can be used by mouth or by slow injection into a vein.[6]

Common side effects include headaches, fever, and nausea.[6] Serious side effects include liver problems, muscle damage, and high blood lactate levels.[6] It is commonly used in pregnancy and appears to be safe for the fetus.[6] ZDV is of the nucleoside analog reverse-transcriptase inhibitor (NRTI) class.[6] It works by inhibiting the enzyme reverse transcriptase that HIV uses to make DNA and therefore decreases replication of the virus.[6]

Zidovudine was first described in 1964.[7] It was resynthesized from a public-domain formula by Burroughs Wellcome.[8] It was approved in the United States in 1987 and was the first treatment for HIV.[6][9] It is on the World Health Organization's List of Essential Medicines.[10][11] It is available as a generic medication.[6]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved October 22, 2023.
  2. ^ "Retrovir 100mg Capsules – Summary of Product Characteristics (SmPC)". (emc). December 14, 2018. Retrieved January 23, 2021.
  3. ^ "Retrovir – zidovudine capsule Retrovir – zidovudine solution Retrovir – zidovudine injection, solution". DailyMed. Retrieved January 23, 2021.
  4. ^ "Active substance: Zidovudine" (PDF). European Medicines Agency. November 30, 2017.
  5. ^ "Zidovudine". PubChem Public Chemical Database. NCBI. Archived from the original on October 25, 2012. Retrieved April 10, 2011.
  6. ^ a b c d e f g h i j k "Zidovudine". The American Society of Health-System Pharmacists. Archived from the original on December 21, 2016. Retrieved November 28, 2016.
  7. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on September 8, 2017.
  8. ^ Linda Marsa, 'Toxic Hope', Los Angeles Times, 20 June 1993
  9. ^ Reeves JD, Derdeyn CA (2007). Entry Inhibitors in HIV Therapy. Springer Science & Business Media. p. 179. ISBN 9783764377830.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list. Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.