Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H11N5O3 |
Molecular Weight | 225.2046 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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)
Molecular Formula | C8H11N5O3 |
Molecular Weight | 225.2046 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://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_YChttp://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdfhttps://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: https://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_YChttp://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020487s016lbl.pdfhttps://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 |
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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 |
|||
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 |
---|---|---|
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs. | 1999 Dec |
|
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain. | 2000 Dec 28 |
|
Anti-herpes simplex virus activities of crude water extracts of Thai medicinal plants. | 2000 Jan |
|
Guanosine analogues as anti-herpesvirus agents. | 2000 Oct-Dec |
|
Interventions for herpes simplex virus epithelial keratitis. | 2001 |
|
Prophylaxis against herpesvirus infections in transplant recipients. | 2001 |
|
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 |
|
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 |
|
Topical treatment of recurrent herpes labialis. | 2001 Jan |
|
Aerobic bacterial and fungal infections in peripheral blood stem cell transplants. | 2001 Jan |
|
8-[18F]Fluoropenciclovir: an improved reporter probe for imaging HSV1-tk reporter gene expression in vivo using PET. | 2001 Jan |
|
Reporter genes and imagene. | 2001 Jan |
|
Coexpression of guanylate kinase with thymidine kinase enhances prodrug cell killing in vitro and suppresses vascular smooth muscle cell proliferation in vivo. | 2001 May |
|
Contact dermatitis from topical antiviral drugs. | 2001 May |
|
Synthesis and biological evaluation of purine-containing butenolides. | 2001 May 24 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2159990
250 mg three times a day for 14 days
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
Fri Dec 15 15:23:38 GMT 2023
by
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on
Fri Dec 15 15:23:38 GMT 2023
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Record UNII |
X4HES1O11F
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C281
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NDF-RT |
N0000175468
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NDF-RT |
N0000175459
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WHO-VATC |
QS01AD03
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FDA ORPHAN DRUG |
313210
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WHO-ESSENTIAL MEDICINES LIST |
21.1
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FDA ORPHAN DRUG |
513615
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WHO-ESSENTIAL MEDICINES LIST |
6.4.1
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WHO-VATC |
QD06BB53
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NDF-RT |
N0000175459
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NDF-RT |
N0000180187
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WHO-ATC |
D06BB03
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WHO-ATC |
D06BB53
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NCI_THESAURUS |
C1556
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WHO-ATC |
J05AB01
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FDA ORPHAN DRUG |
325010
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WHO-VATC |
QD06BB03
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WHO-VATC |
QJ05AB01
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WHO-ATC |
S01AD03
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NDF-RT |
N0000020060
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LIVERTOX |
NBK548548
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NDF-RT |
N0000180188
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NCI_THESAURUS |
C29575
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FDA ORPHAN DRUG |
37589
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NDF-RT |
N0000175459
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1012065
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4829
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DTXSID1022556
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59277-89-3
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758477
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85
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DB00787
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645011
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6511
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100000092808
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X4HES1O11F
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ACICLOVIR
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2453
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CHEMBL184
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Acyclovir
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D000212
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C205
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X4HES1O11F
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4435
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261-685-1
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m1404
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PRIMARY | Merck Index | ||
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ACYCLOVIR
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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. | ||
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281
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135398513
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SUB05235MIG
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PRIMARY |
Related Record | Type | Details | ||
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TRANSPORTER -> SUBSTRATE |
Km
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BINDER->LIGAND |
acyclovir crosses the placenta
BINDING
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE |
Km
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EXCRETED UNCHANGED |
URINE
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TARGET ORGANISM->INHIBITOR |
IC50
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TARGET ORGANISM->INHIBITOR |
IC50
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE |
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TARGET ORGANISM->INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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TRANSPORTER -> SUBSTRATE |
Vmax
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TRANSPORTER -> SUBSTRATE |
Vmax
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ACTIVE CONSTITUENT ALWAYS PRESENT -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
|
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
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Related Record | Type | Details | ||
---|---|---|---|---|
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PRODRUG -> METABOLITE ACTIVE |
|
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE ACTIVE -> PARENT |
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METABOLITE -> PARENT |
MINOR
URINE
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
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IMPURITY -> PARENT |
sum of impurities K and R: not more than 1.5 times the area of the principal peak in the chromatogram obtained with reference solution (b) (0.15 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
sum of impurities A and B: maximum 2.0 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
|
||
|
PARENT -> IMPURITY |
sum of impurities A and B: maximum 2.0 per cent
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)
EP
|
||
|
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 |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
sum of impurities K and R: not more than 1.5 times the area of the principal peak in the chromatogram obtained with reference solution (b) (0.15 per cent)
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 PHARMACOKINETIC |
|
||
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
ORAL BIOAVAILABILITY | PHARMACOKINETIC |
|
|
|||
CSF/PLASMA RATIO | PHARMACOKINETIC |
|
||||
Biological Half-life | PHARMACOKINETIC |
|
|
|||