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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H20N6O4.ClH.2H2O
Molecular Weight 396.827
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALACYCLOVIR HYDROCHLORIDE DIHYDRATE

SMILES

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

InChI

InChIKey=QMVFKSCLPIIINF-CZDIJEQGSA-N
InChI=1S/C13H20N6O4.ClH.2H2O/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;2*1H2/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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
[Cerebral and renal toxicity of acyclovir in a patient treated for meningoencephalitis].
1999 Nov
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
Acyclovir induced coma in the intensive care unit.
2000 Jun
Thienothiadiazine 2,2-dioxide acyclonucleosides: synthesis and antiviral activity.
2000 May
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
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
Rotavirus encephalopathy: pathogenesis reviewed.
2001 Apr
Treatment of EBV driven lymphoproliferation with erythrophagocytosis: 12 year follow up.
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
Biological characterization of eugeniin as an anti-herpes simplex virus type 1 compound in vitro and in vivo.
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
Postherpetic neuralgia. Treatment with amitriptyline is cheaper than with aciclovir.
2001 Apr 7
[Photoallergy to Zovirax cream].
2001 Feb
Painful skin erosions and fever in an infant. Eczema herpeticum.
2001 Feb
Pretransplant varicella vaccination is cost-effective in pediatric renal transplantation.
2001 Feb
Viral etiologies of encephalitis in Thai children.
2001 Feb
Recurrent eczema herpeticum: an underrecognised condition.
2001 Feb
Prophylactic antiviral therapy in CMV high-risk liver transplant recipients.
2001 Feb-Mar
Recurrent herpes labialis: efficacy of topical therapy with penciclovir compared with acyclovir (aciclovir).
2001 Jan
Substantially improved in vivo radiosensitization of rat glioma with mutant HSV-TK and acyclovir.
2001 Jan
Reporter genes and imagene.
2001 Jan
Aseptic meningitis related to valacyclovir.
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
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
Mild herpes simplex encephalitis worsening despite acyclovir treatment.
2001 Mar
[Benign acute ataxia in an adult with VZV infection].
2001 Mar
A pilot study of treatment of herpes labialis with 1072 nm narrow waveband light.
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
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
The management of varicella-zoster virus exposure and infection in pregnancy and the newborn period. Australasian Subgroup in Paediatric Infectious Diseases of the Australasian Society for Infectious Diseases.
2001 Mar 19
Neurotoxicity of valacyclovir in peritoneal dialysis: a pharmacokinetic study.
2001 Mar-Apr
Coexpression of guanylate kinase with thymidine kinase enhances prodrug cell killing in vitro and suppresses vascular smooth muscle cell proliferation in vivo.
2001 May
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 Fri Dec 15 15:47:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:47:46 GMT 2023
Record UNII
A7JO128919
Record Status Validated (UNII)
Record Version
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Name Type Language
VALACYCLOVIR HYDROCHLORIDE DIHYDRATE
Common Name English
L-VALINE, 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER, MONOHYDROCHLORIDE, DIHYDRATE
Common Name English
L-VALINE, 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER, MONOHYDROCHLORIDE DIHYDRATE
Common Name English
L-VALINE, 2-((2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY)ETHYL ESTER, HYDROCHLORIDE, HYDRATE (1:1:2)
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID90198248
Created by admin on Fri Dec 15 15:47:46 GMT 2023 , Edited by admin on Fri Dec 15 15:47:46 GMT 2023
PRIMARY
CAS
502421-45-6
Created by admin on Fri Dec 15 15:47:46 GMT 2023 , Edited by admin on Fri Dec 15 15:47:46 GMT 2023
PRIMARY
PUBCHEM
135565067
Created by admin on Fri Dec 15 15:47:46 GMT 2023 , Edited by admin on Fri Dec 15 15:47:46 GMT 2023
PRIMARY
SMS_ID
100000183986
Created by admin on Fri Dec 15 15:47:46 GMT 2023 , Edited by admin on Fri Dec 15 15:47:46 GMT 2023
PRIMARY
FDA UNII
A7JO128919
Created by admin on Fri Dec 15 15:47:46 GMT 2023 , Edited by admin on Fri Dec 15 15:47:46 GMT 2023
PRIMARY
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