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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
Structure of PENCICLOVIR

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)

HIDE SMILES / InChI

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

Description
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

Curator's Comment: Known to be CNS penetrant in rats. Human data not available.

Originator

Curator's Comment: Beecham Group plc. is a predecessor of GlaxoSmithKline plc.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DENAVIR

Approved Use

DENAVIR® 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 Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

PubMed

TitleDatePubMed
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
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
Patents

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 Mon Mar 31 18:07:11 GMT 2025
Edited
by admin
on Mon Mar 31 18:07:11 GMT 2025
Record UNII
359HUE8FJC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DENAVIR
Preferred Name English
PENCICLOVIR
INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
PENCICLOVIR [USP IMPURITY]
Common Name English
BRL-39123
Code English
NSC-759624
Code English
PENCICLOVIR [VANDF]
Common Name English
PENCICLOVIR [USAN]
Common Name English
9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine
Systematic Name English
PENCICLOVIR [MART.]
Common Name English
2-AMINO-1,9-DIHYDRO-9-(4-HYDROXY-3-(HYDROXYMETHYL)BUTYL)-6H-PURIN-6-ONE
Systematic Name English
Penciclovir [WHO-DD]
Common Name English
penciclovir [INN]
Common Name English
PENCICLOVIR [ORANGE BOOK]
Common Name English
PENCICLOVIR [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AB13
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
NDF-RT N0000175468
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
WHO-VATC QD06BB06
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
NDF-RT N0000020060
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
NCI_THESAURUS C29575
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
WHO-VATC QJ05AB13
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
WHO-ATC D06BB06
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
NCI_THESAURUS C281
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NDF-RT N0000175459
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
NCI_THESAURUS C1556
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
Code System Code Type Description
DRUG CENTRAL
2079
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
WIKIPEDIA
PENCICLOVIR
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
EVMPD
SUB09661MIG
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
DRUG BANK
DB00299
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
NCI_THESAURUS
C66337
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
RXCUI
59839
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY RxNorm
NSC
759624
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
INN
6437
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PRIMARY
CHEBI
7956
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
SMS_ID
100000091073
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL1540
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
HSDB
8123
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
USAN
EE-83
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
MERCK INDEX
m8462
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY Merck Index
FDA UNII
359HUE8FJC
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
LACTMED
Penciclovir
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
CAS
39809-25-1
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
DAILYMED
359HUE8FJC
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID9046491
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
MESH
C053539
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
PUBCHEM
135398748
Created by admin on Mon Mar 31 18:07:11 GMT 2025 , Edited by admin on Mon Mar 31 18:07:11 GMT 2025
PRIMARY
Related Record Type Details
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
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
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
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
METABOLITE INACTIVE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY