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Details

Stereochemistry ACHIRAL
Molecular Formula C8H10N5O3.Na
Molecular Weight 247.1865
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACYCLOVIR SODIUM

SMILES

[Na+].NC1=NC2=C(N=CN2COCCO)C(=O)[N-]1

InChI

InChIKey=RMLUKZWYIKEASN-UHFFFAOYSA-M
InChI=1S/C8H11N5O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C8H10N5O3
Molecular Weight 224.1967
Charge -1
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
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
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
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
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. Treatment with amitriptyline is cheaper than with aciclovir.
2001 Apr 7
Postherpetic neuralgia. Pathogenesis of postherpetic neuralgia should be determined.
2001 Apr 7
[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
Pretransplant varicella vaccination is cost-effective in pediatric renal transplantation.
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
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
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
A 35-year-old man with recurrent aseptic meningitis.
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
FV-100 versus valacyclovir for the prevention of post-herpetic neuralgia and the treatment of acute herpes zoster-associated pain: A randomized-controlled trial.
2017 Jul
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 15:48:03 GMT 2023
Edited
by admin
on Fri Dec 15 15:48:03 GMT 2023
Record UNII
927L42J563
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACYCLOVIR SODIUM
ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
BW-248U-SODIUM
Code English
9-[(2-Hydroxyethoxy)methyl]guanine monosodium salt
Common Name English
ACICLOVIR SODIUM [MART.]
Common Name English
Aciclovir sodium [WHO-DD]
Common Name English
BW-248U SODIUM
Code English
ACYCLOVIR SODIUM SALT
MI  
Common Name English
ACYCLOVIR SODIUM [ORANGE BOOK]
Common Name English
ACYCLOVIR SODIUM [VANDF]
Common Name English
ACICLOVIR SODIUM
MART.   WHO-DD  
Common Name English
ACYCLOVIR SODIUM [USAN]
Common Name English
ACYCLOVIR SODIUM SALT [MI]
Common Name English
BW248U SODIUM
Code English
SODIUM ACYCLOVIR
Common Name English
6H-PURIN-6-ONE, 2-AMINO-1,9-DIHYDRO-9-((2-HYDROXYETHOXY)METHYL)-, MONOSODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
NCI_THESAURUS C29575
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
NCI_THESAURUS C1556
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL184
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
FDA UNII
927L42J563
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
MERCK INDEX
m1404
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C47956
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
PUBCHEM
23665721
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
SMS_ID
100000090487
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
DAILYMED
927L42J563
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID90989774
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
EVMPD
SUB00284MIG
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
DRUG BANK
DBSALT000004
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
USAN
U-98
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
CAS
69657-51-8
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY
RXCUI
81944
Created by admin on Fri Dec 15 15:48:03 GMT 2023 , Edited by admin on Fri Dec 15 15:48:03 GMT 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY