Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H15N5O3 |
Molecular Weight | 253.2578 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(N=CN2CCC(CO)CO)C(=O)N1
InChI
InChIKey=JNTOCHDNEULJHD-UHFFFAOYSA-N
InChI=1S/C10H15N5O3/c11-10-13-8-7(9(18)14-10)12-5-15(8)2-1-6(3-16)4-17/h5-6,16-17H,1-4H2,(H3,11,13,14,18)
Molecular Formula | C10H15N5O3 |
Molecular Weight | 253.2578 |
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 |
---|---|---|
Guanosine analogues as anti-herpesvirus agents. | 2000 Oct-Dec |
|
Genetic risks of antiviral nucleoside analogues--a survey. | 2001 Feb |
|
In vitro and in vivo activity of 1-O-hexadecylpropanediol-3-phospho-ganciclovir and 1-O-hexadecylpropanediol-3-phospho-penciclovir in cytomegalovirus and herpes simplex virus infections. | 2001 Jan |
|
Recurrent herpes labialis: efficacy of topical therapy with penciclovir compared with acyclovir (aciclovir). | 2001 Jan |
|
Topical treatment of recurrent herpes labialis. | 2001 Jan |
|
Ganciclovir and penciclovir, but not acyclovir, induce apoptosis in herpes simplex virus thymidine kinase-transformed baby hamster kidney cells. | 2001 May |
|
Herpes simplex virus: clinical presentation and treatment. | 2001 May |
|
Penciclovir for the treatment of herpes simplex labialis: a review. | 2001 May-Jun |
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Famiciclovir therapy (famvir) for herpes simplex and herpes zoster infections. | 2001 Nov |
|
Pediatric uses of valacyclovir, penciclovir and famciclovir. | 2001 Nov |
|
Preclinical evaluation of the penciclovir analog 9-(4-[(18)F]fluoro-3-hydroxymethylbutyl)guanine for in vivo measurement of suicide gene expression with PET. | 2001 Nov |
|
Separation methods for acyclovir and related antiviral compounds. | 2001 Nov 25 |
|
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 |
|
Viral diseases of the skin: diagnosis and antiviral treatment. | 2002 |
|
[Local treatments using antiviral and non-antiviral drugs for herpes facialis and genitalis (excluding pregnant females and neonates at risk)]. | 2002 Apr |
|
Temporal pattern of herpes simplex virus type 1 infection and cell death in the mouse brain stem: influence of guanosine nucleoside analogues. | 2002 Apr |
|
Effective treatment of herpes simplex labialis with penciclovir cream: combined results of two trials. | 2002 Mar |
|
Current and potential therapies for the treatment of herpes-virus infections. | 2003 |
|
Molecular imaging of protein-protein interactions: controlled expression of p53 and large T-antigen fusion proteins in vivo. | 2003 Apr 15 |
|
Susceptibility of herpes simplex virus isolates to nucleoside analogues and the proportion of nucleoside-resistant variants after repeated topical application of penciclovir to recurrent herpes labialis. | 2003 Apr 15 |
|
Review of antiviral therapy for herpes labialis, genital herpes and herpes zoster. | 2003 Aug |
|
Generation of stable cell lines expressing Lamivudine-resistant hepatitis B virus for antiviral-compound screening. | 2003 Jun |
|
The role of stratum corneum and dermal microvascular perfusion in penetration and tissue levels of water-soluble drugs investigated by microdialysis. | 2003 Mar |
|
Optimization of cellular nucleotide extraction and sample preparation for nucleotide pool analyses using capillary electrophoresis. | 2003 May 5 |
|
Comparison of [18F]FHBG and [14C]FIAU for imaging of HSV1-tk reporter gene expression: adenoviral infection vs stable transfection. | 2003 Nov |
|
Recurrent herpes simplex labialis: selected therapeutic options. | 2003 Sep |
|
Changing paradigms in dermatology: antivirals in dermatology. | 2003 Sep-Oct |
|
Valacyclovir in the treatment of herpes simplex, herpes zoster, and other viral infections. | 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 |
|
Synthesis and biological evaluation of novel tert-azido or tert-amino substituted penciclovir analogs. | 2004 Apr 21 |
|
Antiviral properties and cytotoxic activity of platinum(II) complexes with 1,10-phenanthrolines and acyclovir or penciclovir. | 2004 Aug |
|
Efficacy of antiviral agents in feline herpetic keratitis: results of an in vitro study. | 2004 Aug-Sep |
|
Can clinical trials requiring frequent participant contact be conducted over the Internet? Results from an online randomized controlled trial evaluating a topical ointment for herpes labialis. | 2004 Feb 17 |
|
Therapeutic options for herpes labialis, II: Topical agents. | 2004 Jul |
|
Antiviral drugs in current clinical use. | 2004 Jun |
|
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 |
|
Inactivity of the bicyclic pyrimidine nucleoside analogues against simian varicella virus (SVV) does not correlate with their substrate activity for SVV-encoded thymidine kinase. | 2004 Mar 19 |
|
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 |
|
Penciclovir cream--improved topical treatment for herpes simplex infections. | 2004 Sep-Oct |
|
Drugs for non-HIV viral infections. | 2005 Apr |
|
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 |
|
Platinum(II) complexes with antitumoral/antiviral aromatic heterocycles: effect of glutathione upon in vitro cell growth inhibition. | 2005 May 5 |
|
Clinic-initiated, twice-daily oral famciclovir for treatment of recurrent genital herpes: a randomized, double-blind, controlled trial. | 2005 Oct 15 |
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 |
359HUE8FJC
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
J05AB13
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NDF-RT |
N0000175468
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N0000175459
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QD06BB06
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N0000020060
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NCI_THESAURUS |
C29575
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N0000175459
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QJ05AB13
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WHO-ATC |
D06BB06
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NCI_THESAURUS |
C281
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NDF-RT |
N0000175459
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NCI_THESAURUS |
C1556
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2079
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PENCICLOVIR
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59839
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759624
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359HUE8FJC
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Penciclovir
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39809-25-1
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359HUE8FJC
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DTXSID9046491
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C053539
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135398748
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Related Record | Type | Details | ||
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TARGET ORGANISM->INHIBITOR |
The in vitro activities of penciclovir against HSV-1, HSV-2 and VZV are similar to those of aciclovir, with median IC50 values of 0.4, 1.5 and 4.0?µg/mL, respectively, in MRC-5 cells.
IC50
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TARGET ORGANISM->INHIBITOR |
The in vitro activities of penciclovir against HSV-1, HSV-2 and VZV are similar to those of aciclovir, with median IC50 values of 0.4, 1.5 and 4.0?µg/mL, respectively, in MRC-5 cells.
IC50
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TARGET ORGANISM->INHIBITOR |
The in vitro activities of penciclovir against HSV-1, HSV-2 and VZV are similar to those of aciclovir, with median IC50 values of 0.4, 1.5 and 4.0?µg/mL, respectively, in MRC-5 cells.
IC50
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TRANSPORTER -> SUBSTRATE |
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE INACTIVE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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