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
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
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 |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/3680558 | https://www.ncbi.nlm.nih.gov/pubmed/3790156 | https://www.ncbi.nlm.nih.gov/pubmed/2159990 | Leoung, G.S. (1989) Opportunistic Infections in Patients with the Acquired Immunodeficiency Syndrome, page 207, retrieved from: https://books.google.ru/books?id=As56gGv7E_YChttps://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdfCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6313598 | https://www.ncbi.nlm.nih.gov/pubmed/2828440 | https://www.ncbi.nlm.nih.gov/pubmed/202961
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/3680558 | https://www.ncbi.nlm.nih.gov/pubmed/3790156 | https://www.ncbi.nlm.nih.gov/pubmed/2159990 | Leoung, G.S. (1989) Opportunistic Infections in Patients with the Acquired Immunodeficiency Syndrome, page 207, retrieved from: https://books.google.ru/books?id=As56gGv7E_YChttps://www.accessdata.fda.gov/drugsatfda_docs/label/2005/018828s030,020089s019,019909s020lbl.pdf
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/6313598 | https://www.ncbi.nlm.nih.gov/pubmed/2828440 | https://www.ncbi.nlm.nih.gov/pubmed/202961
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12878501https://www.ncbi.nlm.nih.gov/pubmed/12878501 | https://www.ncbi.nlm.nih.gov/pubmed/20038622
Curator's Comment: Valacyclovir hydrochloride is rapidly converted to acyclovir which was detected in CSF after oral administration of valacyclovir.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1820 |
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Target ID: CHEMBL1872 |
0.08 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZOVIRAX Approved UseOral 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 Date1982 |
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Primary | ZOVIRAX Approved UseOral 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 Date1982 |
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Primary | VALTREX Approved UseINDICATIONS 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 Date2004 |
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Primary | VALTREX Approved UseINDICATIONS 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 Date2004 |
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Primary | VALTRE Approved UseINDICATIONS 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 Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
599.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3015.7 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17692728 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
79% |
ACYCLOVIR plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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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 |
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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11454935
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
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on
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Record UNII |
MZ1IW7Q79D
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C281
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NDF-RT |
N0000175459
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N0000180187
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J05AB11
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NCI_THESAURUS |
C29575
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NCI_THESAURUS |
C1556
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N0000175459
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LIVERTOX |
NBK548655
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WHO-VATC |
QJ05AB11
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NDF-RT |
N0000020060
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N0000175459
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N0000175468
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N0000180188
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SUB00003MIG
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73645
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CHEMBL1349
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C084555
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124832-26-4
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8084
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7106
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DTXSID1023732
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35854
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VALACICLOVIR
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m11355
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2798
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DB00577
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MZ1IW7Q79D
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Valacyclovir
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C28235
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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