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

1982
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

1982
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

2004
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

2004
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

2004
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
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.
1999 Dec
Structure-activity relationships of L-dioxolane uracil nucleosides as anti-Epstein Barr virus agents.
1999 Jun 17
Phenotypic and genetic characterization of thymidine kinase from clinical strains of varicella-zoster virus resistant to acyclovir.
1999 Oct
A rapid phenotypic assay for detection of acyclovir-resistant varicella-zoster virus with mutations in the thymidine kinase open reading frame.
2000 Apr
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
Thienothiadiazine 2,2-dioxide acyclonucleosides: synthesis and antiviral activity.
2000 May
A randomized, double-blind trial of famciclovir versus acyclovir for the treatment of localized dermatomal herpes zoster in immunocompromised patients.
2001
Management of neonatal herpes simplex virus infection.
2001
Recent advances in imaging endogenous or transferred gene expression utilizing radionuclide technologies in living subjects: applications to breast cancer.
2001
Rotavirus encephalopathy: pathogenesis reviewed.
2001 Apr
Heart transplantation and the Batista operation for children with refractory heart failure.
2001 Apr
Treatment of EBV driven lymphoproliferation with erythrophagocytosis: 12 year follow up.
2001 Apr
Acyclovir treatment in 2 patients with benign trigeminal sensory neuropathy.
2001 Apr
Herpes simplex virus-1 thymidine kinase mutants created by semi-random sequence mutagenesis improve prodrug-mediated tumor cell killing.
2001 Apr 1
Practice parameter: Steroids, acyclovir, and surgery for Bell's palsy (an evidence-based review): report of the Quality Standards Subcommittee of the American Academy of Neurology.
2001 Apr 10
Painful skin erosions and fever in an infant. Eczema herpeticum.
2001 Feb
Recurrent eczema herpeticum: an underrecognised condition.
2001 Feb
Meta-analysis of prophylaxis of CMV disease in solid organ transplantation: is Ganciclovir a superior agent to Acyclovir?
2001 Feb-Mar
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
[Valaciclovir in the treatment of initial infection by genital herpes virus: comparative study].
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
Biliary stricture secondary to donor B-cell lymphoma after orthotopic liver transplantation.
2001 Jan
Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation.
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
Crossing diagnostic borders: herpes encephalitis complicated by cultural and language barriers.
2001 Jan-Feb
Mild herpes simplex encephalitis worsening despite acyclovir treatment.
2001 Mar
[Neurologic toxicity caused by zelitrex (valaciclovir) in 3 patients with renal failure. Is overdose associated with improvement of product bioavailability improvement?].
2001 Mar
A 35-year-old man with recurrent aseptic meningitis.
2001 Mar
Ocular tolerability and in vivo bioavailability of poly(ethylene glycol) (PEG)-coated polyethyl-2-cyanoacrylate nanosphere-encapsulated acyclovir.
2001 Mar
[Intrauterine herpes simplex virus infection].
2001 Mar-Apr
Acyclovir prophylaxis in late pregnancy prevents recurrent genital herpes and viral shedding.
2001 May
Contact dermatitis from topical antiviral drugs.
2001 May
Enhancement of the anti-herpetic effect of trichosanthin by acyclovir and interferon.
2001 May 11
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 GMT 2023
Edited
by admin
on Sat Dec 16 16:44:02 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NDF-RT N0000180187
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
WHO-ATC J05AB11
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NCI_THESAURUS C29575
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NCI_THESAURUS C1556
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
LIVERTOX NBK548655
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
WHO-VATC QJ05AB11
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NDF-RT N0000020060
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NDF-RT N0000175459
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NDF-RT N0000175468
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
NDF-RT N0000180188
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
Code System Code Type Description
EVMPD
SUB00003MIG
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
RXCUI
73645
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1349
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
MESH
C084555
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
CAS
124832-26-4
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
HSDB
8084
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
INN
7106
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID1023732
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
CHEBI
35854
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
WIKIPEDIA
VALACICLOVIR
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
PUBCHEM
135398742
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
MERCK INDEX
m11355
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2798
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
DAILYMED
MZ1IW7Q79D
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
SMS_ID
100000092738
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
DRUG BANK
DB00577
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
FDA UNII
MZ1IW7Q79D
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
LACTMED
Valacyclovir
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
NCI_THESAURUS
C28235
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
IUPHAR
4824
Created by admin on Sat Dec 16 16:44:03 GMT 2023 , Edited by admin on Sat Dec 16 16:44:03 GMT 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC