Zidovudine

Zidovudine
Clinical data


Trade names	Retrovir, others
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B3 US: C (Risk not ruled out) (AZT)
Routes of administration	By mouth, IV, rectal suppository
ATC code	J05AF01 (WHO)
Legal status
Legal status	℞ (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
Biological half-life	0.5 to 3 hours
Excretion	kidney and biliary
Identifiers
IUPAC name 1-[(2R,4S,5S)-4-Azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
CAS Number	30516-87-1^Y
PubChem CID	35370
IUPHAR/BPS	4825
DrugBank	DB00495^Y
ChemSpider	32555^Y
UNII	4B9XT59T7S
KEGG	D00413^Y
ChEBI	CHEBI:10110^N
ChEMBL	CHEMBL129^Y
NIAID ChemDB	000001
PDB ligand	AZZ (PDBe, RCSB PDB)
ECHA InfoCard	100.152.492
Chemical and physical data
Formula	C₁₀H₁₃N₅O₄
Molar mass	267.242 g/mol
3D model (Jmol)	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^Y Key:HBOMLICNUCNMMY-XLPZGREQSA-N^Y
^NY (what is this?)

Zidovudine (ZDV), also known as azidothymidine (AZT), is an antiretroviral medication used to prevent and treat HIV/AIDS. It is generally recommended for use with other antiretroviral. 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 baby. 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 approved in the United States in 1986 and was the first treatment for HIV. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is 5.10 to 25.60 USD per month. As of 2015, the cost for a typical month of medication in the United States was more than 200 USD.

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Wikipedia