PENCICLOVIR

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020629s016lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Human herpesvirus 1 DNA polymerase 24 Target ID: CHEMBL1872 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020629s016lbl.pdf	Inhibitor 8504		16.0 µM [Ki]
DNA polymerase catalytic subunit 14 Target ID: P89453 Gene ID: 1487316.0 Gene Symbol: NA Target Organism: Human herpesvirus 2 (strain HG52) (HHV-2) (Human herpes simplex virus\|\|\|2) Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020629s016lbl.pdf	Inhibitor 8504		9.5 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Recurrent herpes labialis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020629s016lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Analyte	Population
0 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020629s016lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020629s016lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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	Analyte	Population
2.24 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
80% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020363s050lbl.pdf	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7956	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7956
ChemicalBook	CB7731886	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7731886
eMolecules	32456333	https://www.emolecules.com/cgi-bin/more?vid=32456333
eMolecules	902282	https://www.emolecules.com/cgi-bin/more?vid=902282
MolPort	MolPort-003-849-798	https://www.molport.com/shop/molecule-link/MolPort-003-849-798
MolPort	MolPort-006-167-513	https://www.molport.com/shop/molecule-link/MolPort-006-167-513
Selleck Chemicals	penciclovir	http://www.selleckchem.com/products/penciclovir.html
ZINC	ZINC000000001899	http://zinc15.docking.org/substances/ZINC000000001899
ChEBI	CHEBI:4974	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4974
ChemicalBook	CB0464901	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0464901
eMolecules	901871	https://www.emolecules.com/cgi-bin/more?vid=901871
MolPort	MolPort-003-666-602	https://www.molport.com/shop/molecule-link/MolPort-003-666-602
Selleck Chemicals	Famciclovir(Famvir)	http://www.selleckchem.com/products/Famciclovir(Famvir).html
ZINC	ZINC000001530635	http://zinc15.docking.org/substances/ZINC000001530635

PubMed

Title	Date	PubMed
Guanosine analogues as anti-herpesvirus agents.	2000 Oct-Dec	11200257
Genetic risks of antiviral nucleoside analogues--a survey.	2001 Feb	11248359
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	11437323
Recurrent herpes labialis: efficacy of topical therapy with penciclovir compared with acyclovir (aciclovir).	2001 Jan	11354919
Topical treatment of recurrent herpes labialis.	2001 Jan	11354913
Ganciclovir and penciclovir, but not acyclovir, induce apoptosis in herpes simplex virus thymidine kinase-transformed baby hamster kidney cells.	2001 May	12959326
Herpes simplex virus: clinical presentation and treatment.	2001 May	11443814
Penciclovir for the treatment of herpes simplex labialis: a review.	2001 May-Jun	11693011
Famiciclovir therapy (famvir) for herpes simplex and herpes zoster infections.	2001 Nov	11753535
Pediatric uses of valacyclovir, penciclovir and famciclovir.	2001 Nov	11734715
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	11696640
Separation methods for acyclovir and related antiviral compounds.	2001 Nov 25	11817033
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	11578910
Viral diseases of the skin: diagnosis and antiviral treatment.	2002	11817982
[Local treatments using antiviral and non-antiviral drugs for herpes facialis and genitalis (excluding pregnant females and neonates at risk)].	2002 Apr	12122334
Temporal pattern of herpes simplex virus type 1 infection and cell death in the mouse brain stem: influence of guanosine nucleoside analogues.	2002 Apr	11879697
Effective treatment of herpes simplex labialis with penciclovir cream: combined results of two trials.	2002 Mar	11934185
Current and potential therapies for the treatment of herpes-virus infections.	2003	12790345
Molecular imaging of protein-protein interactions: controlled expression of p53 and large T-antigen fusion proteins in vivo.	2003 Apr 15	12702563
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	12696003
Review of antiviral therapy for herpes labialis, genital herpes and herpes zoster.	2003 Aug	15482124
Generation of stable cell lines expressing Lamivudine-resistant hepatitis B virus for antiviral-compound screening.	2003 Jun	12760870
The role of stratum corneum and dermal microvascular perfusion in penetration and tissue levels of water-soluble drugs investigated by microdialysis.	2003 Mar	12653734
Optimization of cellular nucleotide extraction and sample preparation for nucleotide pool analyses using capillary electrophoresis.	2003 May 5	12668076
Comparison of [18F]FHBG and [14C]FIAU for imaging of HSV1-tk reporter gene expression: adenoviral infection vs stable transfection.	2003 Nov	14579096
Recurrent herpes simplex labialis: selected therapeutic options.	2003 Sep	12954137
Changing paradigms in dermatology: antivirals in dermatology.	2003 Sep-Oct	14678723
Valacyclovir in the treatment of herpes simplex, herpes zoster, and other viral infections.	2003 Sep-Oct	14505192
In vitro efficacy of ganciclovir, cidofovir, penciclovir, foscarnet, idoxuridine, and acyclovir against feline herpesvirus type-1.	2004 Apr	15077679
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	15018852
Synthesis and biological evaluation of novel tert-azido or tert-amino substituted penciclovir analogs.	2004 Apr 21	15064793
Antiviral properties and cytotoxic activity of platinum(II) complexes with 1,10-phenanthrolines and acyclovir or penciclovir.	2004 Aug	15271515
Efficacy of antiviral agents in feline herpetic keratitis: results of an in vitro study.	2004 Aug-Sep	15512970
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	15111272
Therapeutic options for herpes labialis, II: Topical agents.	2004 Jul	15293698
Antiviral drugs in current clinical use.	2004 Jun	15125867
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?	2004 Mar	15168799
Penciclovir solubility in Eudragit films: a comparison of X-ray, thermal, microscopic and release rate techniques.	2004 Mar 10	15019028
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	14985094
Characterisation of penciclovir resistant acyclovir sensitive herpes simplex virus type 2 isolated from an AIDS patient.	2004 May	15042649
Topical treatment of herpes labialis.	2004 Nov	15605969
Penciclovir cream--improved topical treatment for herpes simplex infections.	2004 Sep-Oct	15452407
Drugs for non-HIV viral infections.	2005 Apr	15767977
Murine cytomegalovirus resistant to antivirals has genetic correlates with human cytomegalovirus.	2005 Aug	16033961
Agents and strategies in development for improved management of herpes simplex virus infection and disease.	2005 Feb	15757392
Recurrent antiviral-resistant genital herpes in an immunocompetent patient.	2005 Jul 1	15942905
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	16041591
Antiadenovirus activities of several classes of nucleoside and nucleotide analogues.	2005 Mar	15728896
Platinum(II) complexes with antitumoral/antiviral aromatic heterocycles: effect of glutathione upon in vitro cell growth inhibition.	2005 May 5	15857142
Clinic-initiated, twice-daily oral famciclovir for treatment of recurrent genital herpes: a randomized, double-blind, controlled trial.	2005 Oct 15	16163627

Patents

Sample Use Guides

In Vivo Use Guide

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 Vitro Use Guide

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

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Name

Type

Language

DENAVIR

Preferred Name

English

PENCICLOVIR

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