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 Date8.4352323E11 |
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 |
|
6.6 μg/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR unknown | 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 unknown | 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 unknown | 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 unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.9 μg/mL |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR unknown | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
17.9 μg × h/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR unknown | 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 unknown | 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 unknown | 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 unknown | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.24 μg × h/mL |
125 mg single, oral dose: 125 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENCICLOVIR unknown | 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 unknown | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 % 12 times / day multiple, topical Recommended Dose: 1 %, 12 times / day Route: topical Route: multiple Dose: 1 %, 12 times / day Sources: Page: Study 024 |
unhealthy, 39 n = 782 Health Status: unhealthy Condition: Recurrent Herpes Simplex Labialis Age Group: 39 Sex: M+F Population Size: 782 Sources: Page: Study 024 |
Disc. AE: Dissociative disorder... AEs leading to discontinuation/dose reduction: Dissociative disorder Sources: Page: Study 024 |
750 mg 3 times / day multiple, oral MTD Dose: 750 mg, 3 times / day Route: oral Route: multiple Dose: 750 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Condition: Herpes zoster Sources: |
|
1500 mg single, oral Recommended Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Herpes labialis Sources: Page: p.1 |
Other AEs: Acute renal failure... Other AEs: Acute renal failure Sources: Page: p.1 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dissociative disorder | Disc. AE | 1 % 12 times / day multiple, topical Recommended Dose: 1 %, 12 times / day Route: topical Route: multiple Dose: 1 %, 12 times / day Sources: Page: Study 024 |
unhealthy, 39 n = 782 Health Status: unhealthy Condition: Recurrent Herpes Simplex Labialis Age Group: 39 Sex: M+F Population Size: 782 Sources: Page: Study 024 |
Acute renal failure | 1500 mg single, oral Recommended Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Herpes labialis Sources: Page: p.1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6.0 |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 7.0 |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
Sources: https://pdf.hres.ca/dpd_pm/00029892.PDF#page=13 Page: 13.0 |
yes | |||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
In vitro activities of penciclovir and acyclovir against herpes simplex virus types 1 and 2. | 1992 Sep |
|
Guanosine analogues as anti-herpesvirus agents. | 2000 Oct-Dec |
|
Current and potential therapies for the treatment of herpesvirus infections. | 2001 |
|
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents. | 2001 Apr-Jul |
|
Antiviral drugs: current state of the art. | 2001 Aug |
|
Topical treatment of recurrent herpes labialis. | 2001 Jan |
|
8-[18F]Fluoropenciclovir: an improved reporter probe for imaging HSV1-tk reporter gene expression in vivo using PET. | 2001 Jan |
|
Recent developments in herpesvirus therapy. | 2001 Mar |
|
Ganciclovir and penciclovir, but not acyclovir, induce apoptosis in herpes simplex virus thymidine kinase-transformed baby hamster kidney cells. | 2001 May |
|
Penciclovir for the treatment of herpes simplex labialis: a review. | 2001 May-Jun |
|
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 |
|
Novel 5-vinyl pyrimidine nucleosides with potent anti-hepatitis B virus activity. | 2001 Nov 19 |
|
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8. | 2001 Nov-Dec |
|
A review of antiviral therapy for herpes labialis. | 2001 Sep |
|
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 |
|
[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 |
|
Comparative analysis of DNA breakage, chromosomal aberrations and apoptosis induced by the anti-herpes purine nucleoside analogues aciclovir, ganciclovir and penciclovir. | 2002 Aug 29 |
|
New treatments for genital herpes. | 2002 Feb |
|
Topical application of penciclovir cream for the treatment of herpes simplex facialis/labialis: a randomized, double-blind, multicentre, aciclovir-controlled trial. | 2002 Jun |
|
Effective treatment of herpes simplex labialis with penciclovir cream: combined results of two trials. | 2002 Mar |
|
The A167Y mutation converts the herpes simplex virus type 1 thymidine kinase into a guanosine analogue kinase. | 2002 May 21 |
|
Assessing the contribution of the herpes simplex virus DNA polymerase to spontaneous mutations. | 2002 May 7 |
|
Antiviral agents: Non-antiretroviral [correction of Nonantiviral] drugs. | 2002 Oct |
|
CL1-SR39: A noninvasive molecular imaging model of prostate cancer suicide gene therapy using positron emission tomography. | 2002 Sep |
|
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 |
|
Brivudine: a herpes virostatic with rapid antiviral activity and once-daily dosing. | 2003 May |
|
Recurrent herpes simplex labialis: selected therapeutic options. | 2003 Sep |
|
Valacyclovir in the treatment of herpes simplex, herpes zoster, and other viral infections. | 2003 Sep-Oct |
|
Inhibition of sickling in vitro by three purine-based antiviral agents: an approach to the treatment of sickle cell disease. | 2003 Sep-Oct |
|
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 |
|
Antiviral properties and cytotoxic activity of platinum(II) complexes with 1,10-phenanthrolines and acyclovir or penciclovir. | 2004 Aug |
|
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 |
|
Recent clinical experience with famciclovir--a "third generation" nucleoside prodrug. | 2004 Sep |
|
Penciclovir cream--improved topical treatment for herpes simplex infections. | 2004 Sep-Oct |
|
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 |
|
Recurrent antiviral-resistant genital herpes in an immunocompetent patient. | 2005 Jul 1 |
|
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides. | 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
by
admin
on
Edited
Fri Dec 16 18:01:35 UTC 2022
by
admin
on
Fri Dec 16 18:01:35 UTC 2022
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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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N0000175468
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N0000175459
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QD06BB06
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N0000020060
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C29575
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N0000175459
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QJ05AB13
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D06BB06
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C281
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N0000175459
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NCI_THESAURUS |
C1556
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2079
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CHEMBL1540
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Penciclovir
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39809-25-1
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C053539
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Related Record | Type | Details | ||
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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 INACTIVE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |