Aciclovir

Aciclovir
Clinical data
Pronunciation/eɪˈsaɪkloʊvɪər/
Trade namesZovirax, others[1]
Other namesAcycloguanosine, acyclovir (BAN UK), acyclovir (USAN US)
AHFS/Drugs.com
MedlinePlusa681045
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Intravenous, by mouth, topical, eye ointment
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability15–20% (by mouth)[3]
Protein binding9–33%[3]
MetabolismLiver
Elimination half-life2–4 hours
ExcretionKidney (62–90% as unchanged drug)
Identifiers
  • 2-amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-3H-purin-6-one
CAS Number
PubChem CID
PubChem SID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.056.059 Edit this at Wikidata
Chemical and physical data
FormulaC8H11N5O3
Molar mass225.208 g·mol−1
3D model (JSmol)
Melting point256.5 °C (493.7 °F)
  • O=C2/N=C(\Nc1n(cnc12)COCCO)N
  • 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) checkY
  • Key:MKUXAQIIEYXACX-UHFFFAOYSA-N checkY
  (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]

  1. ^ a b "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.
  3. ^ 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.
  4. ^ Kevin ES. "The Aciclovir" (in German). Kevin. Retrieved 25 May 2017.
  5. ^ 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.
  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.
  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.
  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
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN 9783527607495.
  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.