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Zidovudine information


Zidovudine
Clinical data
Trade namesRetrovir, others
AHFS/Drugs.comMonograph
MedlinePlusa687007
License data
  • EU EMA: by INN
  • US DailyMed: Zidovudine
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth, intravenous, rectal suppository
ATC code
  • J05AF01 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)[2]
  • US: WARNING[1]Rx-only[3]
  • EU: Rx-only[4]
  • 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 Bile duct
Identifiers
IUPAC name
  • 3'-deoxy-3'-azido-thymidine
    1-[(2R,4S,5S)-4-Azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione[5]
CAS Number
  • 30516-87-1 checkY
PubChem CID
  • 35370
IUPHAR/BPS
  • 4825
DrugBank
  • DB00495 checkY
ChemSpider
  • 32555 checkY
UNII
  • 4B9XT59T7S
KEGG
  • D00413 checkY
ChEBI
  • CHEBI:10110 ☒N
ChEMBL
  • ChEMBL129 checkY
NIAID ChemDB
  • 000001
PDB ligand
  • AZZ (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID8020127 Edit this at Wikidata
ECHA InfoCard100.152.492 Edit this at Wikidata
Chemical and physical data
FormulaC10H13N5O4
Molar mass267.245 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C1NC(C(C)=CN1[C@@H]2O[C@H](CO)[C@@H](N=[N+]=[N-])C2)=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 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.

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It is typically used in combination with other antiretrovirals such as zidovudine, dolutegravir, and abacavir. Lamivudine may be included as part of post-exposure...

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Emtricitabine/tenofovir (emtricitabine + tenofovir) Lamivudine/zidovudine (lamivudine + zidovudine) Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim (isoniazid...

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GSK plc

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Essential Medicines, such as amoxicillin, mercaptopurine, pyrimethamine and zidovudine. In 2012, under prosecution by the United States Department of Justice...

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Glucuronidation

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Chloramphenicol, paracetamol Disease states Fulminant hepatitis, cirrhosis ↓ Zidovudine, oxazepam, lamotrigine Hypothyroidism ↓ Oxazepam, paracetamol HIV ↓ Paracetamol...

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Nevirapine

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prophylaxis with single-dose nevirapine in addition to zidovudine is more effective than zidovudine alone. These and other trials have led the World Health...

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South East England

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Jealott's Hill, being released onto the market in 1958. AZT/Retrovir (zidovudine) was first manufactured by Wellcome in 1987 in Kent; they also introduced...

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abacavir (brand name Ziagen) lamivudine (brand names Epivir and 3TC) zidovudine (brand name Retrovir and AZT) Non-nucleoside reverse transcriptase inhibitors...

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Reverse transcriptase

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reverse-transcriptase inhibitors and include the nucleoside and nucleotide analogues zidovudine (trade name Retrovir), lamivudine (Epivir) and tenofovir (Viread), as...

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Prodrug

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cyclophosphamide, diethylstilbestrol diphosphate, L-DOPA, mercaptopurine, mitomycin, zidovudine Type IB Metabolic tissues (liver, GI mucosal cell, lung etc.) Carbamazepine...

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Compound S

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Compound S may refer to: Cortodoxone Zidovudine, by trade name This disambiguation page lists articles associated with the title Compound S. If an internal...

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ketorolac, naproxen, cephalosporins, quinolones, penicillins, methotrexate, zidovudine, ganciclovir, lorazepam, and acyclovir. In all these interactions, the...

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Aciclovir

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taken when administering aciclovir to patients receiving IV interferon. Zidovudine: Although administered often with aciclovir in HIV patients, neurotoxicity...

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Anemia

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liver disease can also cause macrocytosis. Drugs such as methotrexate, zidovudine, and other substances may inhibit DNA replication such as heavy metals...

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Virus

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to antiviral drugs that inhibit the reverse transcriptase enzyme, e.g. zidovudine and lamivudine. An example of the first type is HIV, which is a retrovirus...

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Clarithromycin

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without dose adjustments. For example, clarithromycin may lead to decreased zidovudine concentrations. Clarithromycin prevents bacteria from multiplying by acting...

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ATC code J05

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Darunavir J05AE11 Ensitrelvir J05AE30 Nirmatrelvir and ritonavir J05AF01 Zidovudine J05AF02 Didanosine J05AF03 Zalcitabine J05AF04 Stavudine J05AF05 Lamivudine...

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David Ho

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free warfarin concentration and prolong bleeding time. Zidovudine: valproate may increase zidovudine serum concentration and lead to toxicity. Although the...

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Dyserythropoiesis

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