Mr. Ibrahem/Zidovudine
Clinical data
Trade namesRetrovir, others
AHFS/Drugs.comMonograph
MedlinePlusa687007
License data
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth, IV, rectal suppository
Legal status
Legal status
  • US: ℞-only
  • In general: ℞ (Prescription only)
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 biliary
Identifiers
  • 3'-deoxy-3'-azido-thymidine
    1-[(2R,4S,5S)-4-Azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione[1]
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), is an antiretroviral medication used to prevent and treat HIV/AIDS.[4] It is generally recommended for use with other antiretrovirals.[4] It may be used to prevent mother-to-child spread during birth or after a needlestick injury or other potential exposure.[4] It is sold both by itself and together as lamivudine/zidovudine and abacavir/lamivudine/zidovudine.[4] It can be used by mouth or by slow injection into a vein.[4]

Common side effects include headaches, fever, and nausea.[4] Serious side effects include liver problems, muscle damage, and high blood lactate levels.[4] It is commonly used in pregnancy and appears to be safe for the baby.[4] ZDV is of the nucleoside analog reverse-transcriptase inhibitor (NRTI) class.[4] It works by inhibiting the enzyme reverse transcriptase that HIV uses to make DNA and therefore decreases replication of the virus.[4]

Zidovudine was first described in 1964.[5] It was approved in the United States in 1987 and was the first treatment for HIV.[4][6] It is on the World Health Organization's List of Essential Medicines.[7] It is available as a generic medication.[4] The wholesale cost in the developing world is US$5.10 to $25.60 per month.[8] As of 2015, the cost for a typical month of medication in the United States was more than $200.[9]

References

edit
  1. ^ "Zidovudine". PubChem Public Chemical Database. NCBI. Archived from the original on October 25, 2012. Retrieved April 10, 2011.
  2. ^ "ZIDOVUDINE = AZT = ZDV oral - Essential drugs". medicalguidelines.msf.org. Archived from the original on August 27, 2021. Retrieved August 25, 2020.
  3. ^ "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on January 22, 2021. Retrieved September 21, 2020.
  4. ^ a b c d e f g h i j k l "Zidovudine". The American Society of Health-System Pharmacists. Archived from the original on December 21, 2016. Retrieved November 28, 2016.
  5. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on September 8, 2017.
  6. ^ Reeves, Jacqueline D.; Derdeyn, Cynthia A. (2007). Entry Inhibitors in HIV Therapy. Springer Science & Business Media. p. 179. ISBN 9783764377830. Archived from the original on April 27, 2021. Retrieved February 11, 2019.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ "Zidovudine". International Drug Price Indicator Guide. Archived from the original on November 14, 2018. Retrieved November 28, 2016.
  9. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 67. ISBN 9781284057560.