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

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H20N6O4.ClH
Molecular Weight 360.797
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALACYCLOVIR HYDROCHLORIDE

SMILES

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

InChI

InChIKey=ZCDDBUOENGJMLV-QRPNPIFTSA-N
InChI=1S/C13H20N6O4.ClH/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);1H/t8-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Selection of an oral prodrug (BRL 42810; famciclovir) for the antiherpesvirus agent BRL 39123 [9-(4-hydroxy-3-hydroxymethylbut-l-yl)guanine; penciclovir].
1989 Oct
Selective activity of various antiviral compounds against HHV-7 infection.
1999 Aug
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
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
The cyclohexene ring system as a furanose mimic: synthesis and antiviral activity of both enantiomers of cyclohexenylguanine.
2000 Feb 24
Anti-herpes simplex virus activities of crude water extracts of Thai medicinal plants.
2000 Jan
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
Thienothiadiazine 2,2-dioxide acyclonucleosides: synthesis and antiviral activity.
2000 May
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
A randomized, double-blind trial of famciclovir versus acyclovir for the treatment of localized dermatomal herpes zoster in immunocompromised patients.
2001
Prophylaxis against herpesvirus infections in transplant recipients.
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
Cough syncope with herpetic tracheobronchitis.
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
[Photoallergy to Zovirax cream].
2001 Feb
Painful skin erosions and fever in an infant. Eczema herpeticum.
2001 Feb
Prophylaxis of intravenous immunoglobulin and acyclovir in perinatal varicella.
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
Persistent verrucous varicella as the initial manifestation of HIV infection.
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
Topical treatment of recurrent herpes labialis.
2001 Jan
Epstein-Barr virus-related lymphoproliferative disease complicating childhood acute lymphoblastic leukemia: no recurrence after unrelated donor bone marrow transplantation.
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
Biliary stricture secondary to donor B-cell lymphoma after orthotopic liver transplantation.
2001 Jan
Susceptibility to acyclovir of herpes simplex virus isolates obtained between 1977 and 1996 in Japan.
2001 Jan
Varicella myocarditis in an adult.
2001 Jan
Crossing diagnostic borders: herpes encephalitis complicated by cultural and language barriers.
2001 Jan-Feb
Mild herpes simplex encephalitis worsening despite acyclovir treatment.
2001 Mar
[Benign acute ataxia in an adult with VZV infection].
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
Predictors of recurrent herpes simplex virus keratitis. Herpetic Eye Disease Study Group.
2001 Mar
Investigation of aciclovir-resistant herpes simplex virus I infection in a bone marrow transplantation unit: genotyping shows that different strains are involved.
2001 Mar
Predictive modeling and heterogeneity of baseline risk in meta-analysis of individual patient data.
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
Contact dermatitis from topical antiviral drugs.
2001 May
Synthesis and biological evaluation of purine-containing butenolides.
2001 May 24
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 Fri Dec 15 15:37:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:37:29 GMT 2023
Record UNII
G447S0T1VC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VALACYCLOVIR HYDROCHLORIDE
MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
VALACICLOVIR HYDROCHLORIDE [MART.]
Common Name English
L-VALINE, 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER, MONOHYDROCHLORIDE
Common Name English
BW-256
Code English
VALTREX
Brand Name English
NSC-759101
Code English
VALACYCLOVIR HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
L-VALINE, ESTER WITH 9-((2-HYDROXYETHOXY)METHYL)GUANINE, MONOHYDROCHLORIDE
Common Name English
VALACYCLOVIR HYDROCHLORIDE [ORANGE BOOK]
Common Name English
VALACYCLOVIR HYDROCHLORIDE [USAN]
Common Name English
VALACICLOVIR HYDROCHLORIDE [JAN]
Common Name English
VALACYCLOVIR HYDROCHLORIDE [MI]
Common Name English
VALACYCLOVIR HYDROCHLORIDE [VANDF]
Common Name English
Valaciclovir hydrochloride [WHO-DD]
Common Name English
256U
Code English
VALACYCLOVIR HYDROCHLORIDE [USP-RS]
Common Name English
VALACICLOVIR HYDROCHLORIDE ANHYDROUS
Common Name English
256-U-87 HYDROCHLORIDE
Code English
BW-256U87
Code English
VALACICLOVIR HYDROCHLORIDE
JAN   MART.   WHO-DD  
Common Name English
VALACYCLOVIR HCL
Common Name English
VALACICLOVIR (AS HYDROCHLORIDE)
Common Name English
256U87 HYDROCHLORIDE
Code English
VALACICLOVIR HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
NCI_THESAURUS C29575
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
NCI_THESAURUS C1556
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
Code System Code Type Description
FDA UNII
G447S0T1VC
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
SMS_ID
100000090390
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
NCI_THESAURUS
C29535
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
RS_ITEM_NUM
1707839
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
NSC
759101
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
MERCK INDEX
m11355
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1349
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
RXCUI
236081
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY RxNorm
CAS
124832-27-5
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
DRUG BANK
DBSALT000289
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
USAN
EE-13
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
PUBCHEM
135398741
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
DAILYMED
G447S0T1VC
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID2044210
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
EVMPD
SUB15679MIG
Created by admin on Fri Dec 15 15:37:30 GMT 2023 , Edited by admin on Fri Dec 15 15:37:30 GMT 2023
PRIMARY
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