Aciclovir

Aciclovir

Clinical data
Pronunciation	/eɪˈsaɪkloʊvɪər/
Trade names	Zovirax, others
AHFS/Drugs.com	Monograph
MedlinePlus	a681045
License data	US FDA: Acyclovir
Pregnancy category	AU: B3 US: B (No risk in non-human studies)
Routes of administration	Intravenous, by mouth, topical (including eye ointment)
ATC code	J05AB01 (WHO) D06BB03 (WHO) S01AD03 (WHO)
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
Bioavailability	15–20% (by mouth)
Protein binding	9–33%
Metabolism	Liver
Biological 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
Synonyms	acycloguanosine
CAS Number	59277-89-3 Y
PubChem (CID)	2022
IUPHAR/BPS	4829
DrugBank	DB00787 Y
ChemSpider	1945 Y
UNII	X4HES1O11F Y
KEGG	D00222 Y
ChEBI	CHEBI:2453 Y
ChEMBL	CHEMBL184 Y
PDB ligand ID	AC2 (PDBe, RCSB PDB)
ECHA InfoCard	100.056.059
Chemical and physical data
Formula	C8H11N5O3
Molar mass	225.21 g·mol−1
3D model (Jmol)	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) Y Key:MKUXAQIIEYXACX-UHFFFAOYSA-N Y

Aciclovir (ACV), 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 or injected.

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 nucleic acid analogue made from guanosine. It works by decreasing the production of the virus's DNA.

The discovery of aciclovir was announced in 1977. It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system. It is available as a generic medication and is marketed under many brand names worldwide. The wholesale cost as of 2014 to 2016 was between US$0.03 and US$0.12 for a typical dose by mouth. The cost of a typical course of treatment in the United States is less than US$25.

Aciclovir is used for the treatment of herpes simplex virus and varicella zoster virus infections, including: