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Details

Stereochemistry ACHIRAL
Molecular Formula C8H11N5O3
Molecular Weight 225.2046
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACYCLOVIR

SMILES

NC1=NC2=C(N=CN2COCCO)C(=O)N1

InChI

InChIKey=MKUXAQIIEYXACX-UHFFFAOYSA-N
InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)

HIDE SMILES / InChI

Molecular Formula C8H11N5O3
Molecular Weight 225.2046
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Valacyclovir is the hydrochloride salt of the L-valyl ester of the antiviral drug acyclovir. Valacyclovir is a nucleoside analog DNA polymerase inhibitor. Valacyclovir hydrochloride is rapidly converted to acyclovir which has demonstrated antiviral activity against HSV types 1 (HSV-1) and 2 (HSV-2) and VZV both in cell culture and in vivo. The inhibitory activity of acyclovir is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts acyclovir into acyclovir monophosphate, a nucleotide analog. The monophosphate is further converted into diphosphate by cellular guanylate kinase and into triphosphate by a number of cellular enzymes. In biochemical assays, acyclovir triphosphate inhibits replication of herpes viral DNA. This is accomplished in 3 ways: 1) competitive inhibition of viral DNA polymerase, 2) incorporation and termination of the growing viral DNA chain, and 3) inactivation of the viral DNA polymerase. The greater antiviral activity of acyclovir against HSV compared with VZV is due to its more efficient phosphorylation by the viral TK. The resistance of HSV and VZV to acyclovir can result from qualitative and quantitative changes in the viral TK and/or DNA polymerase. Clinical isolates of VZV with reduced susceptibility to acyclovir have been recovered from patients with AIDS. Valaciclovir is indicated for the treatment of HSV and VZV infections, including Oral and genital herpes simplex (treatment and prophylaxis), Reduction of HSV transmission from people with recurrent infection to uninfected individuals, Prevention of cytomegalovirus following organ transplantation, Prophylaxis against herpesviruses in immunocompromised patients (such as patients undergoing cancer chemotherapy). Common adverse drug reactions (≥1% of patients) associated with valaciclovir therapy are the same as for aciclovir, its active metabolite, and include nausea, vomiting, diarrhea, and headache. Infrequent adverse effects (0.1–1% of patients) include agitation, vertigo, confusion, dizziness, edema, arthralgia, sore throat, constipation, abdominal pain, rash, weakness and/or renal impairment. Rare adverse effects (<0.1% of patients) include coma, seizures, neutropenia, leukopenia, tremor, ataxia, encephalopathy, psychotic symptoms, crystalluria, anorexia, fatigue, hepatitis, Stevens-Johnson syndrome, toxic epidermal necrolysis and/or anaphylaxis.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Flow cytometric evaluation of antiviral agents against human herpesvirus 6.
2001
Atypical Herpes simplex keratitis (HSK) presenting as a perforated corneal ulcer with a large infiltrate in a contact lens wearer: multinucleated giant cells in the Giemsa smear offered a clue to the diagnosis.
2001
A randomized, double-blind trial of famciclovir versus acyclovir for the treatment of localized dermatomal herpes zoster in immunocompromised patients.
2001
Interventions for herpes simplex virus epithelial keratitis.
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
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
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
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
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
Hydrophilic interaction chromatography using amino and silica columns for the determination of polar pharmaceuticals and impurities.
2001 Apr 13
Postherpetic neuralgia. Pathogenesis of postherpetic neuralgia should be determined.
2001 Apr 7
[Photoallergy to Zovirax cream].
2001 Feb
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
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
Aerobic bacterial and fungal infections in peripheral blood stem cell transplants.
2001 Jan
[Valaciclovir in the treatment of initial infection by genital herpes virus: comparative study].
2001 Jan
Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and 1,2,4-triazol.
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
[Highly active antiviral and immunosuppressive combination therapy with acyclovir and mycophenolate mofetil following keratoplasty in patients with herpetic eye disease].
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
A 35-year-old man with recurrent aseptic meningitis.
2001 Mar
Predictors of recurrent herpes simplex virus keratitis. Herpetic Eye Disease Study Group.
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
[Intrauterine herpes simplex virus infection].
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
Oral recurrent human herpes virus infection and bone marrow transplantation survival.
2001 May
Famciclovir for ophthalmic zoster: a randomised aciclovir controlled study.
2001 May
Acyclovir prophylaxis in late pregnancy prevents recurrent genital herpes and viral shedding.
2001 May
Contact dermatitis from topical antiviral drugs.
2001 May
Chemical stability, enzymatic hydrolysis, and nasal uptake of amino acid ester prodrugs of acyclovir.
2001 May
Enhancement of the anti-herpetic effect of trichosanthin by acyclovir and interferon.
2001 May 11
Synthesis and biological evaluation of purine-containing butenolides.
2001 May 24
Patents

Sample Use Guides

In Vivo Use Guide
Acute Treatment of Herpes Zoster: 800 mg every 4 hours orally, 5 times daily for 7 to 10 days. Genital Herpes: Treatment of Initial Genital Herpes: 200 mg every 4 hours, 5 times daily for 10 days.
Route of Administration: oral, parenteral, topical
In Vitro Use Guide
Penciclovir (PCV) and acyclovir are acyclic guanine analogs which inhibit herpes simplex virus (HSV) DNA polymerase. Their 50% infective doses were 0.5 to 0.8 microgram/ml for clinical isolates of HSV-1 and 1.3 to 2.2 micrograms/ml for HSV-2.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:51:26 UTC 2019
Edited
by admin
on Mon Oct 21 19:51:26 UTC 2019
Record UNII
X4HES1O11F
Record Status Validated (UNII)
Record Version
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Name Type Language
ACYCLOVIR
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
SITAVIG
Brand Name English
ZOVIRAX
Brand Name English
ACICLOVIR [INN]
Common Name English
ACYCLOVIR [USP]
Common Name English
ACYCLOVIR [VANDF]
Common Name English
ACICLOVIR [JAN]
Common Name English
ACICLOVIR
EP   INN   JAN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
ACYCLOVIR [USP-RS]
Common Name English
ACICLOVIR [WHO-IP]
Common Name English
ACICLOVIR [MART.]
Common Name English
ACYCLOVIR [HSDB]
Common Name English
ACICLOVIR [EP]
Common Name English
GERPEVIR
Common Name English
NOVIRUS
Common Name English
9-((2-HYDROXYETHOXY)METHYL)GUANINE
Systematic Name English
ACICLOVIR [WHO-DD]
Common Name English
6H-PURIN-6-ONE, 2-AMINO-1,9-DIHYDRO-9-((2-HYDROXYETHOXY)METHYL)-
Systematic Name English
ACYCLOVIR [MI]
Common Name English
ACICLOVIR [IARC]
Common Name English
ACYCLOVIR [ORANGE BOOK]
Common Name English
NSC-645011
Code English
AVACLYR
Brand Name English
ACYCLOVIR [USAN]
Common Name English
ACICLOVIRUM [WHO-IP]
Common Name English
VALACICLOVIR HYDROCHLORIDE, ANHYDROUS SPECIFIED IMPURITY B [EP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NDF-RT N0000175468
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-VATC QS01AD03
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
FDA ORPHAN DRUG 313210
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 21.1
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
FDA ORPHAN DRUG 513615
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.4.1
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-VATC QD06BB53
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NDF-RT N0000180187
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-ATC D06BB03
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-ATC D06BB53
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NCI_THESAURUS C1556
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-ATC J05AB01
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-VATC QD06BB03
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-VATC QJ05AB01
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
FDA ORPHAN DRUG 325010
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
WHO-ATC S01AD03
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NDF-RT N0000020060
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
LIVERTOX 14
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NDF-RT N0000180188
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NCI_THESAURUS C29575
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
FDA ORPHAN DRUG 37589
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
NDF-RT N0000175459
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
Code System Code Type Description
IUPHAR
4829
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
EPA CompTox
59277-89-3
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
CAS
59277-89-3
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
DRUG BANK
DB00787
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
HSDB
59277-89-3
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
PUBCHEM
2022
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
WIKIPEDIA
ACICLOVIR
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
ChEMBL
CHEMBL184
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
MESH
D000212
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
NCI_THESAURUS
C205
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
INN
4435
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
ECHA (EC/EINECS)
261-685-1
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
MERCK INDEX
M1404
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
ACYCLOVIR
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY Description: White or almost white, crystalline powder. Solubility: Slightly soluble in water; freely soluble in dimethyl sulfoxide; very slightly soluble in ethanol (96%). It dissolves in dilute solutions of mineral acids and alkali hydroxides. Category: Antiviral (Purine nucleoside analogue). Storage: Preserve in well-closed containers. Protect from light and moisture. Additional information: Aciclovir may exhibit polymorphism. Definition: Aciclovir contains not less than 98.5% and not more than 101.0% of C8H11N5O3, calculated with reference to the dried substance.
RXCUI
281
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY RxNorm
LactMed
59277-89-3
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
EVMPD
SUB05235MIG
Created by admin on Mon Oct 21 19:51:26 UTC 2019 , Edited by admin on Mon Oct 21 19:51:26 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Km
BINDER->LIGAND
acyclovir crosses the placenta
BINDING
TRANSPORTER -> SUBSTRATE
Km
EXCRETED UNCHANGED
URINE
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
Vmax
ACTIVE CONSTITUENT ALWAYS PRESENT -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE -> PARENT
A small amount was delected in one stool sample
MINOR
URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
IDENTIFIED AS IMPURITY K The following peaks are eluted at the following relative retention with reference to the peak of aciclovir (retention time about 13 min): impurity K about 2.5.
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
ACYCLOVIR IMPURITY L AMOUNT NOT SPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
ACYCLOVIR IMPURITY M AMOUNT NOT SPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Cmax PHARMACOKINETIC ROUTE OF ADMINSTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC
CSF/PLASMA RATIO PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC