Aciclovir

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

Aciclovir
Clinical data
Pronunciation/ˈsklvɪər/
Trade namesZovirax, others
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
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability15–20% (by mouth)
Protein binding9–33%
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
Chemical and physical data
FormulaC8H11N5O3
Molar mass225.208 g·mol−1
3D model (JSmol)
Melting point256.5 °C (493.7 °F)
SMILES
  • 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) Y
  • Key:MKUXAQIIEYXACX-UHFFFAOYSA-N Y
  (verify)

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

Aciclovir was patented in 1974 by Burroughs Wellcome, and approved for medical use in 1981. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication and is marketed under many brand names worldwide. In 2021, it was the 169th most commonly prescribed medication in the United States, with more than 3 million prescriptions.

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