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: WARNINGRx-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.^[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]

^ "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.
^ "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". PubChem Public Chemical Database. NCBI. Archived from the original on October 25, 2012. Retrieved April 10, 2011.
^ ^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.
^ Linda Marsa, 'Toxic Hope', Los Angeles Times, 20 June 1993
^ Reeves JD, Derdeyn CA (2007). Entry Inhibitors in HIV Therapy. Springer Science & Business Media. p. 179. ISBN 9783764377830.
^ 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.
^ 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.

[FDA-AllBoxedWarnings-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.

[AHFS2016-6] ^ ^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.

[latimes.com-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.

[WHO21st-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.

[WHO22nd-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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