File:Zidovudine.svg · Wikimedia Commons · See Wikimedia Commons
zidovudine
Sign in to saveAlso known as 3'-azido-3'-deoxythymidine, AZT, Retrovir®, Azidothymidine, ZDV, Zidovudinum, Zidovudin
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. It may be used to prevent mother-to-child spread during birth or after a needlestick injury or other potential exposure. It is sold both by itself and together as lamivudine/zidovudine and abacavir/lamivudine/zidovudine. It can be used by mouth or by slow injection into a vein.
OverviewAI-generated
Zidovudine is a chemical compound with the formula C₁₀H₁₃N₅O₄. Its IUPAC name is 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione. The substance has a mass of 267.097 and a weight of 267.24. It possesses a charge of 0, an xlogp of 0, and a topological polar surface area of 93.2. The molecule contains two hydrogen bond donors and six hydrogen bond acceptors.
The compound is associated with a PubMed query count of 13050. It is referenced by 358 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.N
- 5
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 441946513
- Drug.image
- Zidovudine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 155
- Drug.image2
- Zidovudine-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Retrovir, others
- Drug.MedlinePlus
- a687007
- Drug.DailyMedID
- Zidovudine
- Drug.pregnancy_AU
- B3
- Drug.licence_EU
- yes
- Drug.routes_of_administration
- By mouth, intravenous, rectal suppository
- Drug.ATC_prefix
- J05
- Drug.ATC_suffix
- AF01
- Drug.legal_UK
- POM
via Wikipedia infobox
Chemical data
- Formula
- C10H13N5O4
- Molecular weight
- 267.24 g/mol
- IUPAC name
- 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
- SMILES
- CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
- InChIKey
- HBOMLICNUCNMMY-XLPZGREQSA-N
- XLogP
- 0
- Polar surface area
- 93.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1987
- Admin. routes
- oral, parenteral
- Indications
- HIV infection, HIV-1 infection, infection, Kaposi's sarcoma
via ChEMBL · EBI
Research
13,050 papers- Zidovudine (Retrovir) update.CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne · 1990
- Zidovudine intolerance.Reviews of infectious diseases · 1990
- Lamivudine/zidovudine/abacavir: triple combination tablet.Drugs · 2003
- Zidovudine: five years later.Annals of internal medicine · 1992
- Zidovudine: a review of its use in the management of vertically-acquired pediatric HIV infection.Paediatric drugs · 2002
via PubMed
Wikidata facts
- Subclass of
- nucleoside analogue
- Mass
- 267.097
- Has use
- medication
Show 11 more facts
- chemical formula
- C₁₀H₁₃N₅O₄
- significant drug interaction
- ribavirin
- route of administration
- rectal administration
- Commons category
- Zidovudine
- medical condition treated
- HIV infection
- canonical SMILES
- CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-]
- isomeric SMILES
- CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)N=[N+]=[N-]
- World Health Organisation international non-proprietary name
- zidovudine
- subject has role
- essential medicine
- found in taxon
- Stachybotrys chartarum
- legal status (medicine)
- boxed warning
Sources (6)
via Wikidata · CC0
~16 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- HIV treatment
- HIV prevention
- Antibacterial properties
- Side effects
- Viral resistance
- Mechanism of action
- Chemistry
- History
- Initial cancer research
- HIV/AIDS research
- Patent filed and FDA approval
- Society and culture
- References
- External links
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. It may be used to prevent mother-to-child spread during birth or after a needlestick injury or other potential exposure. It is sold both by itself and together as lamivudine/zidovudine and abacavir/lamivudine/zidovudine. It can be used by mouth or by slow injection into a vein.
Common side effects include headaches, fever, and nausea. Serious side effects include liver problems, muscle damage, and high blood lactate levels. It is commonly used in pregnancy and appears to be safe for the fetus. ZDV is of the nucleoside analog reverse-transcriptase inhibitor (NRTI) class. It works by inhibiting the enzyme reverse transcriptase that HIV uses to make DNA and therefore decreases replication of the virus.
Excerpted from Wikipedia’s “zidovudine” article, available under the CC BY-SA 4.0 licence.