Valaciclovir

Valaciclovir
Clinical data
Trade names	Valtrex, Zelitrex, others
Other names	valacyclovir, valacyclovir hydrochloride (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a695010
License data	US DailyMed: Valacyclovir;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
Drug class	Antiviral
ATC code	J05AB11 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	55%
Protein binding	13–18%
Metabolism	Liver (to aciclovir)
Elimination half-life	<30 minutes (valaciclovir);; 2.5–3.6 hours (aciclovir)
Excretion	Kidney 40–50% (aciclovir),; faecal 47% (aciclovir)
Identifiers
	IUPAC name 2-[(2-Amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate;
CAS Number	124832-26-4 ; as HCl: 124832-27-5;
PubChem CID	135398742; as HCl: 135398741;
IUPHAR/BPS	4824;
DrugBank	DB00577 ; as HCl: DBSALT000289;
ChemSpider	54770 ;
UNII	MZ1IW7Q79D; as HCl: G447S0T1VC;
KEGG	D08664 ; as HCl: D00398;
ChEBI	CHEBI:35854 ; as HCl: CHEBI:9919;
ChEMBL	ChEMBL1349 ; as HCl: ChEMBL1201110;
NIAID ChemDB	070982;
CompTox Dashboard (EPA)	DTXSID1023732 ;
ECHA InfoCard	100.114.479
Chemical and physical data
Formula	C13H20N6O4
Molar mass	324.341 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OCCOCn1c2N\C(=N/C(=O)c2nc1)N)[C@@H](N)C(C)C;
	InChI InChI=1S/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1 ; Key:HDOVUKNUBWVHOX-QMMMGPOBSA-N ;
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Valaciclovir, also spelled valacyclovir, is an antiviral medication used to treat outbreaks of herpes simplex or herpes zoster (shingles).^[2] It is also used to prevent cytomegalovirus following a kidney transplant in high risk cases.^[2] It is taken by mouth.^[2]

Common side effects include headache and vomiting.^[2] Severe side effects may include kidney problems.^[2] Use in pregnancy appears to be safe.^[2] It is a prodrug, which works after being converted to aciclovir in a person's body.^[2]

Valaciclovir was patented in 1987 and came into medical use in 1995.^[3]^[4] It is on the World Health Organization's List of Essential Medicines.^[5] It is available as a generic medication.^[6] In 2021, it was the 114th most commonly prescribed medication in the United States, with more than 5 million prescriptions.^[7]^[8]

^ "Valtrex- valacyclovir hydrochloride tablet, film coated". DailyMed. 14 June 2021. Retrieved 22 May 2022.
^ ^a ^b ^c ^d ^e ^f ^g "Valacyclovir Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 17 March 2019.
^ Long SS, Pickering LK, Prober CG (2012). Principles and Practice of Pediatric Infectious Disease. Elsevier Health Sciences. p. 1502. ISBN 978-1437727029.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN 9783527607495.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 625–626. ISBN 9780857113382.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Valacyclovir - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.