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)
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 |
---|---|---|
Perspectives for the treatment of hepatitis B virus infections. | 1999 Jul |
|
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 |
|
Current and potential therapies for the treatment of herpesvirus infections. | 2001 |
|
Antiviral drugs: current state of the art. | 2001 Aug |
|
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 |
|
Pharmacokinetic studies of 2-amino-9-(3-acetoxymethyl-4-isopropoxycarbonyl-oxybut-1-yl)purine, an oral prodrug for the antiviral agent penciclovir. | 2001 Jul |
|
Famiciclovir therapy (famvir) for herpes simplex and herpes zoster infections. | 2001 Nov |
|
Novel 5-vinyl pyrimidine nucleosides with potent anti-hepatitis B virus activity. | 2001 Nov 19 |
|
Separation methods for acyclovir and related antiviral compounds. | 2001 Nov 25 |
|
A review of antiviral therapy for herpes labialis. | 2001 Sep |
|
Viral diseases of the skin: diagnosis and antiviral treatment. | 2002 |
|
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 |
|
Drugs for non-HIV viral infections. | 2002 Feb 4 |
|
Comparison of methods for identifying resistant herpes simplex virus and measuring antiviral susceptibility. | 2002 Jan |
|
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 |
|
[4'-Thio-5-ethyl-2'-deoxyuridine 5'-phosphonates: synthesis and antiviral activity]. | 2002 Sep-Oct |
|
Current and potential therapies for the treatment of herpes-virus infections. | 2003 |
|
Novel agents and strategies to treat herpes simplex virus infections. | 2003 Feb |
|
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 |
|
Optimization of cellular nucleotide extraction and sample preparation for nucleotide pool analyses using capillary electrophoresis. | 2003 May 5 |
|
Profiling penciclovir susceptibility and prevalence of resistance of herpes simplex virus isolates across eleven clinical trials. | 2003 Sep |
|
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 |
|
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 |
|
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
J05AB13
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
NDF-RT |
N0000175468
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
NDF-RT |
N0000175459
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
WHO-VATC |
QD06BB06
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
NDF-RT |
N0000020060
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
NCI_THESAURUS |
C29575
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
NDF-RT |
N0000175459
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
WHO-VATC |
QJ05AB13
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
WHO-ATC |
D06BB06
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
NCI_THESAURUS |
C281
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
NDF-RT |
N0000175459
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
||
|
NCI_THESAURUS |
C1556
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
2079
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
PENCICLOVIR
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
SUB09661MIG
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
DB00299
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
C66337
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
59839
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | RxNorm | ||
|
759624
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
6437
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
7956
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
100000091073
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
CHEMBL1540
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
8123
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
EE-83
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
m8462
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | Merck Index | ||
|
359HUE8FJC
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
Penciclovir
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
39809-25-1
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
359HUE8FJC
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
DTXSID9046491
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
C053539
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY | |||
|
135398748
Created by
admin on Fri Dec 15 15:44:24 UTC 2023 , Edited by admin on Fri Dec 15 15:44:24 UTC 2023
|
PRIMARY |
ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)