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. 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.

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