Zidovudine

Zidovudine
Clinical data
Trade names	Retrovir, others
AHFS/Drugs.com	Monograph
MedlinePlus	a687007
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); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Complete absorption, following first-pass metabolism systemic availability 75% (range 52 to 75%)
Protein binding	30 to 38%
Metabolism	Liver
Elimination half-life	0.5 to 3 hours
Excretion	Kidney 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;
CAS Number	30516-87-1 ;
PubChem CID	35370;
IUPHAR/BPS	4825;
DrugBank	DB00495 ;
ChemSpider	32555 ;
UNII	4B9XT59T7S;
KEGG	D00413 ;
ChEBI	CHEBI:10110 ;
ChEMBL	ChEMBL129 ;
NIAID ChemDB	000001;
PDB ligand	AZZ (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8020127 ;
ECHA InfoCard	100.152.492
Chemical and physical data
Formula	C10H13N5O4
Molar mass	267.245 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 ; Key:HBOMLICNUCNMMY-XLPZGREQSA-N ;
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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.^[5] It may be used to prevent mother-to-child spread during birth or after a needlestick injury or other potential exposure.^[5] It is sold both by itself and together as lamivudine/zidovudine and abacavir/lamivudine/zidovudine.^[5] It can be used by mouth or by slow injection into a vein.^[5]

Common side effects include headaches, fever, and nausea.^[5] Serious side effects include liver problems, muscle damage, and high blood lactate levels.^[5] It is commonly used in pregnancy and appears to be safe for the fetus.^[5] ZDV is of the nucleoside analog reverse-transcriptase inhibitor (NRTI) class.^[5] It works by inhibiting the enzyme reverse transcriptase that HIV uses to make DNA and therefore decreases replication of the virus.^[5]

Zidovudine was first described in 1964.^[6] It was resynthesized from a public-domain formula by Burroughs Wellcome.^[7] It was approved in the United States in 1987 and was the first treatment for HIV.^[5]^[8] It is on the World Health Organization's List of Essential Medicines.^[9] It is available as a generic medication.^[5]

^ "Retrovir 100mg Capsules – Summary of Product Characteristics (SmPC)". (emc). December 14, 2018. Retrieved January 23, 2021.
^ "Retrovir – zidovudine capsule Retrovir – zidovudine solution Retrovir – zidovudine injection, solution". DailyMed. Retrieved January 23, 2021.
^ "Active substance: Zidovudine" (PDF). European Medicines Agency. November 30, 2017.
^ Zidovudine from PubChem
^ ^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.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 505. ISBN 9783527607495. Archived from the original on September 8, 2017.
^ Marsa L (June 20, 1993). "TOXIC HOPE : WIDELY EMBRACED, THE AIDS DRUG IS NOW UNDER HEAVY FIRE. : THE AZT STORY". Los Angeles Times.
^ Reeves JD, Derdeyn CA (2007). Entry Inhibitors in HIV Therapy. Springer Science & Business Media. p. 179. ISBN 9783764377830.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.