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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
The S-acyl-2-thioethyl pronucleotide approach applied to acyclovir: part I. Synthesis and in vitro anti-hepatitis B virus activity of bis(S-acyl-2-thioethyl)phosphotriester derivatives of acyclovir.
1999 Jan
Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'alpha-C-branched-chain sugar pyrimidine nucleosides.
1999 Jul 29
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
Acute renal insufficiency due to oral acyclovir in a man with sickle cell trait.
1999 Nov
Phenotypic and genetic characterization of thymidine kinase from clinical strains of varicella-zoster virus resistant to acyclovir.
1999 Oct
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
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine.
2000 Feb 24
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
Guanosine analogues as anti-herpesvirus agents.
2000 Oct-Dec
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
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
Acyclovir treatment in 2 patients with benign trigeminal sensory neuropathy.
2001 Apr
Biological characterization of eugeniin as an anti-herpes simplex virus type 1 compound in vitro and in vivo.
2001 Apr
Postherpetic neuralgia. Pathogenesis of postherpetic neuralgia should be determined.
2001 Apr 7
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
Eczema herpeticum in parthenium dermatitis.
2001 Feb
Antiviral drugs can inhibit lymphocyte apoptosis induced by cytomegalovirus antigens.
2001 Feb-Mar
[Valaciclovir in the treatment of initial infection by genital herpes virus: comparative study].
2001 Jan
Substantially improved in vivo radiosensitization of rat glioma with mutant HSV-TK and acyclovir.
2001 Jan
Recurrent lumbosacral herpes simplex in the bedridden hospitalized patient.
2001 Jan
Herpetic folliculitis and syringitis simulating acne excoriée.
2001 Jan
Neonatal herpes simplex and incontinentia pigmenti.
2001 Jan-Feb
[Highly active antiviral and immunosuppressive combination therapy with acyclovir and mycophenolate mofetil following keratoplasty in patients with herpetic eye disease].
2001 Mar
Predictors of recurrent herpes simplex virus keratitis. Herpetic Eye Disease Study Group.
2001 Mar
Predictive modeling and heterogeneity of baseline risk in meta-analysis of individual patient data.
2001 Mar
[Intrauterine herpes simplex virus infection].
2001 Mar-Apr
Oral recurrent human herpes virus infection and bone marrow transplantation survival.
2001 May
Acyclovir prophylaxis in late pregnancy prevents recurrent genital herpes and viral shedding.
2001 May
Contact dermatitis from topical antiviral drugs.
2001 May
Patents

Sample Use Guides

Valacyclovir may be given without regard to meals. Cold Sores (Herpes Labialis): The recommended dosage of Valacyclovir for treatment of cold sores is 2 grams twice daily for 1 day taken 12 hours apart. Therapy should be initiated at the earliest symptom of a cold sore. Genital Herpes: Initial Episode: The recommended dosage of Valacyclovir for treatment of initial genital herpes is 1 gram twice daily for 10 days. Therapy was most effective when administered within 48 hours of the onset of signs and symptoms. Recurrent Episodes: The recommended dosage of Valacyclovir for treatment of recurrent genital herpes is 500 mg twice daily for 3 days. Initiate treatment at the first sign or symptom of an episode.
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 Wed Apr 02 08:20:13 GMT 2025
Edited
by admin
on Wed Apr 02 08:20:13 GMT 2025
Record UNII
MZ1IW7Q79D
Record Status Validated (UNII)
Record Version
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Name Type Language
VALACYCLOVIR
MI   VANDF  
Common Name English
VALACICLOVIR
INN   WHO-DD  
INN  
Preferred 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
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 Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NDF-RT N0000175459
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NDF-RT N0000180187
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
WHO-ATC J05AB11
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NCI_THESAURUS C29575
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NCI_THESAURUS C1556
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NDF-RT N0000175459
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
LIVERTOX NBK548655
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
WHO-VATC QJ05AB11
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NDF-RT N0000020060
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NDF-RT N0000175459
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NDF-RT N0000175468
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
NDF-RT N0000180188
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
Code System Code Type Description
EVMPD
SUB00003MIG
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
RXCUI
73645
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL1349
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
MESH
C084555
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
CAS
124832-26-4
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
HSDB
8084
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
INN
7106
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
EPA CompTox
DTXSID1023732
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
CHEBI
35854
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
WIKIPEDIA
VALACICLOVIR
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
PUBCHEM
135398742
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
MERCK INDEX
m11355
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY Merck Index
DRUG CENTRAL
2798
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
DAILYMED
MZ1IW7Q79D
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
SMS_ID
100000092738
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
DRUG BANK
DB00577
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
FDA UNII
MZ1IW7Q79D
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
LACTMED
Valacyclovir
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
NCI_THESAURUS
C28235
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
IUPHAR
4824
Created by admin on Wed Apr 02 08:20:13 GMT 2025 , Edited by admin on Wed Apr 02 08:20:13 GMT 2025
PRIMARY
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