Aciclovir

Aciclovir
Aciclovir 2D structure.svg
Aciclovir ball-and-stick 2KI5.png
Clinical data
Pronunciation/ˈsklvɪər/
Trade namesZovirax, others[1]
Other namesAcycloguanosine, acyclovir (BAN UK), acyclovir (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa681045
License data
Pregnancy
category
  • AU: B3
Routes of
administration
Intravenous, by mouth, topical, eye ointment
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) for tablet and injection. Unscheduled for cream form under 10 g.
  • CA: ℞-only
  • UK: POM (Prescription only) for tablet and injection. GSL (OTC) for cream form under 2 g.
  • US: ℞-only
Pharmacokinetic data
Bioavailability15–20% (by mouth)[2]
Protein binding9–33%[2]
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 (ACV), also known as acyclovir, is an antiviral medication.[3] It is primarily used for the treatment of herpes simplex virus infections, chickenpox, and shingles.[4] Other uses include prevention of cytomegalovirus infections following transplant and severe complications of Epstein-Barr virus infection.[4][5] It can be taken by mouth, applied as a cream, or injected.[4]

Common side effects include nausea and diarrhea.[4] Potentially serious side effects include kidney problems and low platelets.[4] Greater care is recommended in those with poor liver or kidney function.[4] It is generally considered safe for use in pregnancy with no harm having been observed.[4][6] It appears to be safe during breastfeeding.[7][8] Aciclovir is a nucleoside analogue that mimics guanosine.[4] It works by decreasing the production of the virus's DNA.[4]

Aciclovir was patented in 1974, and approved for medical use in 1981.[9] It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system.[10] It is available as a generic medication and is marketed under many brand names worldwide.[1] In 2018, it was the 151st most commonly prescribed medication in the United States, with more than 4 million prescriptions.[11][12]

  1. ^ a b "Aciclovir". Drugs.com. Archived from the original on 23 September 2015. Retrieved 6 September 2015.
  2. ^ 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.
  3. ^ de Clercq, Erik; Field, Hugh J (5 October 2005). "Antiviral prodrugs – the development of successful prodrug strategies for antiviral chemotherapy". British Journal of Pharmacology. 147 (1). Wiley-Blackwell (published January 2006). pp. 1–11. doi:10.1038/sj.bjp.0706446. PMC 1615839. PMID 16284630.
  4. ^ 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.
  5. ^ Rafailidis PI, Mavros MN, Kapaskelis A, Falagas ME (2010). "Antiviral treatment for severe EBV infections in apparently immunocompetent patients". Journal of Clinical Virology. 49 (3): 151–7. doi:10.1016/j.jcv.2010.07.008. PMID 20739216.
  6. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  7. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 59. ISBN 9781284057560.
  8. ^ "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
  9. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN 9783527607495.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  11. ^ "The Top 300 of 2021". ClinCalc. Retrieved 18 February 2021.
  12. ^ "Acyclovir - Drug Usage Statistics". ClinCalc. Archived from the original on 9 July 2018. Retrieved 18 February 2021.