Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C13H20N6O4.ClH.H2O |
Molecular Weight | 378.812 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.CC(C)[C@H](N)C(=O)OCCOCN1C=NC2=C1N=C(N)NC2=O
InChI
InChIKey=KNOVZDRKHSHEQN-JZGIKJSDSA-N
InChI=1S/C13H20N6O4.ClH.H2O/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;1H2/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 |
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 |
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 |
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 |
|||
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 |
|||
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 |
|||
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 |
|||
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 |
|||
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 |
|
[Cerebral and renal toxicity of acyclovir in a patient treated for meningoencephalitis]. | 1999 Nov |
|
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses. | 2000 Mar |
|
Thienothiadiazine 2,2-dioxide acyclonucleosides: synthesis and antiviral activity. | 2000 May |
|
Cough syncope with herpetic tracheobronchitis. | 2001 Apr |
|
Heart transplantation and the Batista operation for children with refractory heart failure. | 2001 Apr |
|
Acyclovir treatment in 2 patients with benign trigeminal sensory neuropathy. | 2001 Apr |
|
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 |
|
Persistent verrucous varicella as the initial manifestation of HIV infection. | 2001 Feb |
|
Epstein-Barr virus-related lymphoproliferative disease complicating childhood acute lymphoblastic leukemia: no recurrence after unrelated donor bone marrow transplantation. | 2001 Jan |
|
Herpetic folliculitis and syringitis simulating acne excoriée. | 2001 Jan |
|
Management of the neonate whose mother received suppressive acyclovir therapy during late pregnancy. | 2001 Jan |
|
Susceptibility to acyclovir of herpes simplex virus isolates obtained between 1977 and 1996 in Japan. | 2001 Jan |
|
Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation. | 2001 Jan 15 |
|
A pilot study of treatment of herpes labialis with 1072 nm narrow waveband light. | 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 |
|
Acyclovir prophylaxis in late pregnancy prevents recurrent genital herpes and viral shedding. | 2001 May |
|
Contact dermatitis from topical antiviral drugs. | 2001 May |
|
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 |
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
by
admin
on
Edited
Mon Mar 31 21:58:56 GMT 2025
by
admin
on
Mon Mar 31 21:58:56 GMT 2025
|
Record UNII |
JF64RVR4E3
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
1218948-84-5
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
NON-SPECIFIC STOICHIOMETRY | |||
|
SUB37499
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
PRIMARY | |||
|
JF64RVR4E3
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
PRIMARY | |||
|
135428922
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
PRIMARY | |||
|
521915-75-3
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
PRIMARY | |||
|
SUB126884
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
PRIMARY | |||
|
JF64RVR4E3
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
PRIMARY | |||
|
2604686
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
PRIMARY | |||
|
100000129151
Created by
admin on Mon Mar 31 21:58:56 GMT 2025 , Edited by admin on Mon Mar 31 21:58:56 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ANHYDROUS->SOLVATE |
|
||
|
PARENT -> SALT/SOLVATE |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
sum of impurities A and B: maximum 2.0 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
|
||
|
IMPURITY -> PARENT |
sum of impurities A and B: maximum 2.0 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|