U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H20N6O4
Molecular Weight 324.3357
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALACYCLOVIR

SMILES

CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N=C(N)NC2=O

InChI

InChIKey=HDOVUKNUBWVHOX-QMMMGPOBSA-N
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

HIDE SMILES / InChI

Molecular Formula C13H20N6O4
Molecular Weight 324.3357
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Acyclovir is a synthetic antiviral nucleoside analogue. A screening program for antiviral drugs begun at Burroughs Wellcome in the 1960s resulted in the discovery of acyclovir in 1974. Preclinical investigation brought the drug to clinical trials in 1977 and the first form of the drug (topical) was available to physicians in 1982. Activity of acyclovir is greatest against herpes 1 and herpes 2, less against varicella zoster, still less against Epstein-Barr, and very little against cytomegalovirus. Acyclovir is an antiviral agent only after it is phosphorylated in infected cells by a viral-induced thymidine kinase. Acyclovir monophosphate is phosphorylated to diphosphate and triphosphate forms by cellular enzymes in the infected host cell where the drug is concentrated. Acyclovir triphosphate inactivates viral deoxyribonucleic acid polymerase.

CNS Activity

Curator's Comment: Valacyclovir hydrochloride is rapidly converted to acyclovir which was detected in CSF after oral administration of valacyclovir.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZOVIRAX

Approved Use

Oral ZOVIRAX® (acyclovir) is indicated for the treatment: Herpes Zoster Infections: ZOVIRAX is indicated for the acute treatment of herpes zoster (shingles). Genital Herpes: ZOVIRAX is indicated for the treatment of initial episodes and the management of recurrent episodes of genital herpes. Chickenpox: ZOVIRAX is indicated for the treatment of chickenpox (varicella). Injectable ZOVIRAX® (acyclovir) is indicated for the treatment: Herpes Simplex Infections in Immunocompromised Patients: ZOVIRAX for Injection is indicated for the treatment of initial and recurrent mucosal and cutaneous herpes simplex (HSV-1 and HSV-2) in immunocompromised patients. Initial Episodes of Herpes Genitalis: ZOVIRAX for Injection is indicated for the treatment of severe initial clinical episodes of herpes genitalis in immunocompetent patients. Herpes Simplex Encephalitis: ZOVIRAX for Injection is indicated for the treatment of herpessimplex encephalitis. Neonatal Herpes Simplex Virus Infection: ZOVIRAX for Injection is indicated for the treatmentof neonatal herpes infections. Varicella-Zoster Infections in Immunocompromised Patients: ZOVIRAX for Injection is indicated for the treatment of varicella-zoster (shingles) infections in immunocompromised patients.

Launch Date

3.86208006E11
Primary
ZOVIRAX

Approved Use

Oral ZOVIRAX® (acyclovir) is indicated for the treatment: Herpes Zoster Infections: ZOVIRAX is indicated for the acute treatment of herpes zoster (shingles). Genital Herpes: ZOVIRAX is indicated for the treatment of initial episodes and the management of recurrent episodes of genital herpes. Chickenpox: ZOVIRAX is indicated for the treatment of chickenpox (varicella). Injectable ZOVIRAX® (acyclovir) is indicated for the treatment: Herpes Simplex Infections in Immunocompromised Patients: ZOVIRAX for Injection is indicated for the treatment of initial and recurrent mucosal and cutaneous herpes simplex (HSV-1 and HSV-2) in immunocompromised patients. Initial Episodes of Herpes Genitalis: ZOVIRAX for Injection is indicated for the treatment of severe initial clinical episodes of herpes genitalis in immunocompetent patients. Herpes Simplex Encephalitis: ZOVIRAX for Injection is indicated for the treatment of herpessimplex encephalitis. Neonatal Herpes Simplex Virus Infection: ZOVIRAX for Injection is indicated for the treatmentof neonatal herpes infections. Varicella-Zoster Infections in Immunocompromised Patients: ZOVIRAX for Injection is indicated for the treatment of varicella-zoster (shingles) infections in immunocompromised patients.

Launch Date

3.86208006E11
Primary
VALTREX

Approved Use

INDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients.

Launch Date

1.07896321E12
Primary
VALTREX

Approved Use

INDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients.

Launch Date

1.07887683E12
Primary
VALTRE

Approved Use

INDICATIONS AND USAGE. VALTREX is a nucleoside analogue DNA polymerase inhibitor indicated for: Adult Patients Cold Sores (Herpes Labialis), Genital Herpes, Treatment in immunocompetent patients (initial or recurrent episode), Suppression in immunocompetent or HIV-infected patients, Reduction of transmission, Herpes Zoster. Pediatric Patients Cold Sores (Herpes Labialis), Chickenpox Limitations of Use. The efficacy and safety of VALTREX have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients.

Launch Date

1.07887683E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
599.2 ng/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACYCLOVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3015.7 ng × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACYCLOVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.9 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACYCLOVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
79%
ACYCLOVIR plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Selective activity of various antiviral compounds against HHV-7 infection.
1999 Aug
Evaluation of anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]- guanine (A-5021) in mice.
1999 Jun
[Cerebral and renal toxicity of acyclovir in a patient treated for meningoencephalitis].
1999 Nov
Hepatic and renal effects of azidothymidine and acyclovir on pregnant rats.
2000
A rapid phenotypic assay for detection of acyclovir-resistant varicella-zoster virus with mutations in the thymidine kinase open reading frame.
2000 Apr
Synthesis and antiviral activity of acyclovir-5'-(phenyl methoxy alaninyl) phosphate as a possible membrane-soluble nucleotide prodrug.
2000 Apr 3
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.
2000 Dec 28
Anti-herpes simplex virus activities of crude water extracts of Thai medicinal plants.
2000 Jan
Antiviral effect of brassinosteroids against herpes virus and arenaviruses.
2000 Jan
Acyclovir induced coma in the intensive care unit.
2000 Jun
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
Metabolism and mode of inhibition of varicella-zoster virus by L-beta-5-bromovinyl-(2-hydroxymethyl)-(1,3-dioxolanyl)uracil is dependent on viral thymidine kinase.
2000 Nov
Anti-(herpes simplex virus) activity of 4'-thio-2'-deoxyuridines: a biochemical investigation for viral and cellular target enzymes.
2000 Oct 15
Guanosine analogues as anti-herpesvirus agents.
2000 Oct-Dec
Interventions for herpes simplex virus epithelial keratitis.
2001
Management of neonatal herpes simplex virus infection.
2001
Heart transplantation and the Batista operation for children with refractory heart failure.
2001 Apr
Famciclovir vs. aciclovir in immunocompetent patients with recurrent genital herpes infections: a parallel-groups, randomized, double-blind clinical trial.
2001 Apr
[Peptide transporter family].
2001 Apr
Prophylaxis of intravenous immunoglobulin and acyclovir in perinatal varicella.
2001 Feb
Pretransplant varicella vaccination is cost-effective in pediatric renal transplantation.
2001 Feb
Anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)-cycloprop-1'-yl]methyl] x guanine (A-5021) in vitro and in vivo.
2001 Feb
Genetic risks of antiviral nucleoside analogues--a survey.
2001 Feb
Viral etiologies of encephalitis in Thai children.
2001 Feb
Eczema herpeticum in parthenium dermatitis.
2001 Feb
Recurrent eczema herpeticum: an underrecognised condition.
2001 Feb
Prophylactic antiviral therapy in CMV high-risk liver transplant recipients.
2001 Feb-Mar
Antiviral drugs can inhibit lymphocyte apoptosis induced by cytomegalovirus antigens.
2001 Feb-Mar
Recurrent herpes labialis: efficacy of topical therapy with penciclovir compared with acyclovir (aciclovir).
2001 Jan
Topical treatment of recurrent herpes labialis.
2001 Jan
Aerobic bacterial and fungal infections in peripheral blood stem cell transplants.
2001 Jan
Recurrent lumbosacral herpes simplex in the bedridden hospitalized patient.
2001 Jan
8-[18F]Fluoropenciclovir: an improved reporter probe for imaging HSV1-tk reporter gene expression in vivo using PET.
2001 Jan
Reporter genes and imagene.
2001 Jan
Aseptic meningitis related to valacyclovir.
2001 Jan
Management of the neonate whose mother received suppressive acyclovir therapy during late pregnancy.
2001 Jan
Isolation and analysis of an aciclovir-resistant murine cytomegalovirus mutant.
2001 Jan
Longitudinal analysis of varicella-zoster virus DNA on the ocular surface associated with herpes zoster ophthalmicus.
2001 Jan
Varicella myocarditis in an adult.
2001 Jan
Successful outcome with a "quintuple approach" of posttransplant lymphoproliferative disorder.
2001 Jan 15
Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and 1,2,4-triazol.
2001 Jan-Feb
Progressive outer retinal necrosis in a patient with nephrotic syndrome.
2001 Jan-Feb
Selection and characterization of varicella-zoster virus variants resistant to (R)-9-[4-hydroxy-2-(hydroxymethy)butyl]guanine.
2001 Jun
Mild herpes simplex encephalitis worsening despite acyclovir treatment.
2001 Mar
A pilot study of treatment of herpes labialis with 1072 nm narrow waveband light.
2001 Mar
A 35-year-old man with recurrent aseptic meningitis.
2001 Mar
Predictive modeling and heterogeneity of baseline risk in meta-analysis of individual patient data.
2001 Mar
Oral recurrent human herpes virus infection and bone marrow transplantation survival.
2001 May
Contact dermatitis from topical antiviral drugs.
2001 May
Diagnosis and Treatment of Acute Retinal Necrosis: A Report by the American Academy of Ophthalmology.
2017 Mar
Patents

Sample Use Guides

250 mg three times a day for 14 days
Route of Administration: Oral
In uptake studies using valacyclovir, the extraction solution (water/methanol, 50:50) was added to the Caco-2 cells after the uptake period. After standing for 1 h at room temperature, the solutions were centrifuged and the supernatants were filtered. The filtrate was analyzed by highperformance liquid chromatography (HPLC). Valacyclovir showed a marked inhibitory effect (K=440 +/- 29mkM) on [14C]glycylsarcosine uptake via the apical PEPT1.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:44:02 UTC 2023
Edited
by admin
on Sat Dec 16 16:44:02 UTC 2023
Record UNII
MZ1IW7Q79D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VALACYCLOVIR
MI   VANDF  
Common Name English
Valaciclovir [WHO-DD]
Common Name English
L-VALINE 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER
Systematic Name English
VALACICLOVIR
INN   WHO-DD  
INN  
Official Name English
VALACYCLOVIR [MI]
Common Name English
VALACV
Common Name English
valaciclovir [INN]
Common Name English
L-VALINE, 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER
Common Name English
L-VALINE, ESTER WITH 9-((2-HYDROXYETHOXY)METHYL)GUANINE
Common Name English
VALACYCLOVIR [VANDF]
Common Name English
L-VALINE ESTER WITH 9-((2-HYDROXYETHOXY)METHYL)GUANINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NDF-RT N0000180187
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
WHO-ATC J05AB11
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NCI_THESAURUS C29575
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NCI_THESAURUS C1556
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
LIVERTOX NBK548655
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
WHO-VATC QJ05AB11
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NDF-RT N0000020060
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NDF-RT N0000175468
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
NDF-RT N0000180188
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
Code System Code Type Description
EVMPD
SUB00003MIG
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
RXCUI
73645
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1349
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
MESH
C084555
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
CAS
124832-26-4
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
HSDB
8084
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
INN
7106
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID1023732
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
CHEBI
35854
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
WIKIPEDIA
VALACICLOVIR
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
PUBCHEM
135398742
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
MERCK INDEX
m11355
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
2798
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
DAILYMED
MZ1IW7Q79D
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
SMS_ID
100000092738
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
DRUG BANK
DB00577
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
FDA UNII
MZ1IW7Q79D
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
LACTMED
Valacyclovir
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
NCI_THESAURUS
C28235
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
IUPHAR
4824
Created by admin on Sat Dec 16 16:44:03 UTC 2023 , Edited by admin on Sat Dec 16 16:44:03 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC