Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H19N5O4 |
Molecular Weight | 321.3318 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O
InChI
InChIKey=GGXKWVWZWMLJEH-UHFFFAOYSA-N
InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)
Molecular Formula | C14H19N5O4 |
Molecular Weight | 321.3318 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/3040998 |
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020363s037lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2754699
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/3040998 |
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020363s037lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/2754699
Penciclovir (DENAVIR®) is a synthetic acyclic guanine derivative with antiviral activity, mainly used to treat infections from herpes simplex virus (HSV) types 1 and 2. In cells infected with HSV-1 or HSV-2, the viral thymidine kinase phosphorylates penciclovir to a monophosphate form that, in turn, is converted by cellular kinases to the active form penciclovir triphosphate. Biochemical studies demonstrate that penciclovir triphosphate inhibits HSV polymerase competitively with deoxyguanosine triphosphate. Consequently, herpes viral DNA synthesis and, therefore, replication are selectively inhibited. Famciclovir (FAMVIR®) is a prodrug form of penciclovir with improved oral bioavailability.
CNS Activity
Sources: http://avc.sagepub.com/content/8/3/275.full.pdf
Curator's Comment: Known to be CNS penetrant in rats. Human data not available.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3631945
Curator's Comment: Beecham Group plc. is a predecessor of GlaxoSmithKline plc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1872 |
16.0 µM [Ki] | ||
Target ID: P89453 Gene ID: 1487316.0 Gene Symbol: NA Target Organism: Human herpesvirus 2 (strain HG52) (HHV-2) (Human herpes simplex virus|||2) |
9.5 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DENAVIR Approved UseDENAVIR® is a nucleoside analog HSV DNA polymerase inhibitor indicated for the treatment of recurrent herpes labialis (cold sores) in adults and children 12 years of age and older. Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0 ng/mL |
1.8 mg single, topical dose: 1.8 mg route of administration: Topical experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0 ng/mL |
1.8 mg 1 times / day steady-state, topical dose: 1.8 mg route of administration: Topical experiment type: STEADY-STATE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.8 μg/mL |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.3 μg/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4 μg/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6.6 μg/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.6 μg/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.24 μg × h/mL |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
8.95 μg × h/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
12.1 μg × h/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
17.9 μg × h/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
4.48 μg × h/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.3 h |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
80% |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
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 |
|
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 |
|
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues. | 1999 Jun 15 |
|
Lamivudine, adefovir and tenofovir exhibit long-lasting anti-hepatitis B virus activity in cell culture. | 2000 Jan |
|
Absence of rapid selection for acyclovir or penciclovir resistance following suboptimal oral prodrug therapy of HSV-infected mice. | 2001 |
|
Recent advances in imaging endogenous or transferred gene expression utilizing radionuclide technologies in living subjects: applications to breast cancer. | 2001 |
|
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents. | 2001 Apr-Jul |
|
Antiviral drugs: current state of the art. | 2001 Aug |
|
Genetic risks of antiviral nucleoside analogues--a survey. | 2001 Feb |
|
Topical treatment of recurrent herpes labialis. | 2001 Jan |
|
Pediatric uses of valacyclovir, penciclovir and famciclovir. | 2001 Nov |
|
Separation methods for acyclovir and related antiviral compounds. | 2001 Nov 25 |
|
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8. | 2001 Nov-Dec |
|
A simplified one-pot synthesis of 9-[(3-[18F]fluoro-1-hydroxy-2-propoxy)methyl]guanine([18F]FHPG) and 9-(4-[18F]fluoro-3-hydroxymethylbutyl)guanine ([18F]FHBG) for gene therapy. | 2001 Oct |
|
Comparison of new topical treatments for herpes labialis: efficacy of penciclovir cream, acyclovir cream, and n-docosanol cream against experimental cutaneous herpes simplex virus type 1 infection. | 2001 Sep |
|
Viral diseases of the skin: diagnosis and antiviral treatment. | 2002 |
|
Topical application of penciclovir cream for the treatment of herpes simplex facialis/labialis: a randomized, double-blind, multicentre, aciclovir-controlled trial. | 2002 Jun |
|
Changing paradigms in dermatology: antivirals in dermatology. | 2003 Sep-Oct |
|
In vitro efficacy of ganciclovir, cidofovir, penciclovir, foscarnet, idoxuridine, and acyclovir against feline herpesvirus type-1. | 2004 Apr |
|
Once, twice, or three times daily famciclovir compared with aciclovir for the oral treatment of herpes zoster in immunocompetent adults: a randomized, multicenter, double-blind clinical trial. | 2004 Apr |
|
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir? | 2004 Mar |
|
Penciclovir solubility in Eudragit films: a comparison of X-ray, thermal, microscopic and release rate techniques. | 2004 Mar 10 |
|
Characterisation of penciclovir resistant acyclovir sensitive herpes simplex virus type 2 isolated from an AIDS patient. | 2004 May |
|
Topical treatment of herpes labialis. | 2004 Nov |
|
Drugs for non-HIV viral infections. | 2005 Apr |
|
Altered deoxyribonucleotide pools in T-lymphoblastoid cells expressing the multisubstrate nucleoside kinase of Drosophila melanogaster. | 2005 Aug |
|
Murine cytomegalovirus resistant to antivirals has genetic correlates with human cytomegalovirus. | 2005 Aug |
|
Agents and strategies in development for improved management of herpes simplex virus infection and disease. | 2005 Feb |
|
Recurrent antiviral-resistant genital herpes in an immunocompetent patient. | 2005 Jul 1 |
|
Comparison of [14C]FMAU, [3H]FEAU, [14C]FIAU, and [3H]PCV for monitoring reporter gene expression of wild type and mutant herpes simplex virus type 1 thymidine kinase in cell culture. | 2005 Jul-Aug |
|
Antiadenovirus activities of several classes of nucleoside and nucleotide analogues. | 2005 Mar |
|
Development and validation of a new reversed-phase ion pairing liquid chromatographic method with fluorescence detection for penciclovir analysis in plasma and aqueous humor. | 2005 Nov 5 |
|
Clinic-initiated, twice-daily oral famciclovir for treatment of recurrent genital herpes: a randomized, double-blind, controlled trial. | 2005 Oct 15 |
|
In vitro activity of cycloSal-nucleoside monophosphates and polyhydroxycarboxylates against orthopoxviruses. | 2005 Sep |
Sample Use Guides
Penciclovir (DENAVIR®) should be applied every 2 hours during waking hours for a period of 4 days. Treatment should be started as early as possible (i.e., during the prodrome or when lesions appear).
Route of Administration:
Topical
In cell culture studies, penciclovir has antiviral activity against the following herpes viruses: HSV-1 and HSV-2. The antiviral activity of penciclovir against wild type strains grown on human foreskin fibroblasts was assessed with a plaque reduction assay and staining with crystal violet 3 days postinfection for HSV. The median EC50 values of penciclovir against laboratory and clinical isolates of HSV-1 and HSV-2 were 2 uM (range 1.2 to 2.4 uM, n=7) and 2.6 uM (range 1.6 to 11 uM, n=6), respectively.
Substance Class |
Chemical
Created
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Record UNII |
QIC03ANI02
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
J05AB09
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WHO-ATC |
S01AD07
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NDF-RT |
N0000020060
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NDF-RT |
N0000180187
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LIVERTOX |
NBK547978
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NDF-RT |
N0000175459
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QS01AD07
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WHO-VATC |
QJ05AB09
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NDF-RT |
N0000175459
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NCI_THESAURUS |
C29575
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NCI_THESAURUS |
C281
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NDF-RT |
N0000175459
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m5240
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C29044
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68099
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FAMCICLOVIR
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Famciclovir
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DB00426
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QIC03ANI02
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CHEMBL880
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DTXSID0023038
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1269152
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3324
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METABOLITE ACTIVE -> PRODRUG |
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URINE
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METABOLITE INACTIVE -> PARENT |
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URINE
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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