Aciclovir

Aciclovir
Clinical data
Pronunciation	/eɪˈsaɪkloʊvɪər/
Trade names	Zovirax, others
Other names	Acycloguanosine, acyclovir (BAN UK), acyclovir (USAN US)
AHFS/Drugs.com	Acyclovir Monograph; Acyclovir topical Monograph;
MedlinePlus	a681045
License data	US DailyMed: Acyclovir;
Pregnancy; category	AU: B3; ;
Routes of; administration	Intravenous, by mouth, topical, eye ointment
ATC code	J05AB01 (WHO) D06BB03 (WHO), S01AD03 (WHO), D06BB53 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	15–20% (by mouth)
Protein binding	9–33%
Metabolism	Liver
Elimination half-life	2–4 hours
Excretion	Kidney (62–90% as unchanged drug)
Identifiers
	IUPAC name 2-amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-3H-purin-6-one;
CAS Number	59277-89-3 ;
PubChem CID	2022;
PubChem SID	46506002;
IUPHAR/BPS	4829;
DrugBank	DB00787 ;
ChemSpider	1945 ;
UNII	X4HES1O11F;
KEGG	D00222 ; C06810 ;
ChEBI	CHEBI:2453 ;
ChEMBL	ChEMBL184 ;
PDB ligand	AC2 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1022556 ;
ECHA InfoCard	100.056.059
Chemical and physical data
Formula	C8H11N5O3
Molar mass	225.208 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	256.5 °C (493.7 °F)
	SMILES O=C2/N=C(\Nc1n(cnc12)COCCO)N;
	InChI InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15) ; Key:MKUXAQIIEYXACX-UHFFFAOYSA-N ;
	(verify)

Aciclovir, also known as acyclovir,^[4] is an antiviral medication.^[5] It is primarily used for the treatment of herpes simplex virus infections, chickenpox, and shingles.^[6] Other uses include, prevention of cytomegalovirus infections following transplant, and severe complications of Epstein–Barr virus infection.^[6]^[7] It can be taken by mouth, applied as a cream, or injected.^[6]

Common side effects include nausea and diarrhea.^[6] Potentially serious side effects include kidney problems and low platelets.^[6] Greater care is recommended in those with poor liver or kidney function.^[6] It is generally considered safe for use in pregnancy with no harm having been observed.^[6]^[8] It appears to be safe during breastfeeding.^[9]^[10] Aciclovir is a nucleoside analogue that mimics guanosine.^[6] It works by decreasing the production of the virus's DNA.^[6]

Aciclovir was patented in 1974, by Burroughs Wellcome, and approved for medical use in 1981.^[11] It is on the World Health Organization's List of Essential Medicines.^[12] It is available as a generic medication and is marketed under many brand names worldwide.^[1] In 2022, it was the 134th most commonly prescribed medication in the United States, with more than 4 million prescriptions.^[13]^[14]

^ ^a ^b "Aciclovir". Drugs.com. Archived from the original on 23 September 2015. Retrieved 6 September 2015.
^ "Skin health". Health Canada. 9 May 2018. Retrieved 13 April 2024.
^ ^a ^b "Zovirax (acyclovir) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 19 February 2014. Retrieved 5 February 2014.
^ Kevin ES. "The Aciclovir" (in German). Kevin. Retrieved 25 May 2017.
^ de Clercq E, Field HJ (5 October 2005). "Antiviral prodrugs – the development of successful prodrug strategies for antiviral chemotherapy". British Journal of Pharmacology. Vol. 147, no. 1. Wiley-Blackwell (published January 2006). pp. 1–11. doi:10.1038/sj.bjp.0706446. PMC 1615839. PMID 16284630.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Acyclovir". The American Society of Health-System Pharmacists. Archived from the original on 2015-01-05. Retrieved Jan 1, 2015.
^ Rafailidis PI, Mavros MN, Kapaskelis A, Falagas ME (November 2010). "Antiviral treatment for severe EBV infections in apparently immunocompetent patients". Journal of Clinical Virology. 49 (3): 151–157. doi:10.1016/j.jcv.2010.07.008. PMID 20739216.
^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 59. ISBN 9781284057560.
^ "Acyclovir use while Breastfeeding". Mar 10, 2015. Archived from the original on 5 March 2016. Retrieved 8 March 2016. Even with the highest maternal dosages, the dosage of acyclovir in milk is only about 1% of a typical infant dosage and would not be expected to cause any adverse effects in breastfed infants
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN 9783527607495.
^ 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.
^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
^ "Acyclovir Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

[Names-1] "Aciclovir". Drugs.com. Archived from the original on 23 September 2015. Retrieved 6 September 2015.

[2] "Skin health". Health Canada. 9 May 2018. Retrieved 13 April 2024.

[MSR-3] "Zovirax (acyclovir) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 19 February 2014. Retrieved 5 February 2014.

[4] Kevin ES. "The Aciclovir" (in German). Kevin. Retrieved 25 May 2017.

[deClercq2005-5] Clercq E, Field HJ (5 October 2005). "Antiviral prodrugs – the development of successful prodrug strategies for antiviral chemotherapy". British Journal of Pharmacology. Vol. 147, no. 1. Wiley-Blackwell (published January 2006). pp. 1–11. doi:10.1038/sj.bjp.0706446. PMC 1615839. PMID 16284630.

[AHFS2015-6] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Acyclovir". The American Society of Health-System Pharmacists. Archived from the original on 2015-01-05. Retrieved Jan 1, 2015.

[pmid20739216-7] Rafailidis PI, Mavros MN, Kapaskelis A, Falagas ME (November 2010). "Antiviral treatment for severe EBV infections in apparently immunocompetent patients". Journal of Clinical Virology. 49 (3): 151–157. doi:10.1016/j.jcv.2010.07.008. PMID 20739216.

[8] "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.

[Ric2015-9] Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 59. ISBN 9781284057560.

[10] "Acyclovir use while Breastfeeding". Mar 10, 2015. Archived from the original on 5 March 2016. Retrieved 8 March 2016. Even with the highest maternal dosages, the dosage of acyclovir in milk is only about 1% of a typical infant dosage and would not be expected to cause any adverse effects in breastfed infants

[Fis2006-11] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN 9783527607495.

[WHO23rd-12] 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.

[13] "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.

[14] "Acyclovir Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

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Aciclovir

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