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
Development and validation of a new reversed-phase ion pairing liquid chromatographic method with fluorescence detection for penciclovir analysis in plasma and aqueous humor.	2005-11-05	16140045
Clinic-initiated, twice-daily oral famciclovir for treatment of recurrent genital herpes: a randomized, double-blind, controlled trial.	2005-10-15	16163627
In vitro activity of cycloSal-nucleoside monophosphates and polyhydroxycarboxylates against orthopoxviruses.	2005-09	16076502
Altered deoxyribonucleotide pools in T-lymphoblastoid cells expressing the multisubstrate nucleoside kinase of Drosophila melanogaster.	2005-08	16045762
Murine cytomegalovirus resistant to antivirals has genetic correlates with human cytomegalovirus.	2005-08	16033961
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.	2005-07-26	16041591
Recurrent antiviral-resistant genital herpes in an immunocompetent patient.	2005-07-01	15942905
Platinum(II) complexes with antitumoral/antiviral aromatic heterocycles: effect of glutathione upon in vitro cell growth inhibition.	2005-05-05	15857142
Drugs for non-HIV viral infections.	2005-04	15767977
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides.	2005-03	15728906
Antiadenovirus activities of several classes of nucleoside and nucleotide analogues.	2005-03	15728896
Agents and strategies in development for improved management of herpes simplex virus infection and disease.	2005-02	15757392
Topical treatment of herpes labialis.	2004-11	15605969
Efficacy of antiviral agents in feline herpetic keratitis: results of an in vitro study.	2004-10-30	15512970
Recent clinical experience with famciclovir--a "third generation" nucleoside prodrug.	2004-09	15535046
Antiviral properties and cytotoxic activity of platinum(II) complexes with 1,10-phenanthrolines and acyclovir or penciclovir.	2004-08	15271515
Therapeutic options for herpes labialis, II: Topical agents.	2004-07	15293698
Antiviral drugs in current clinical use.	2004-06	15125867
Characterisation of penciclovir resistant acyclovir sensitive herpes simplex virus type 2 isolated from an AIDS patient.	2004-05	15042649
Synthesis and biological evaluation of novel tert-azido or tert-amino substituted penciclovir analogs.	2004-04-21	15064793
In vitro efficacy of ganciclovir, cidofovir, penciclovir, foscarnet, idoxuridine, and acyclovir against feline herpesvirus type-1.	2004-04	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.	2004-04	15018852
Inactivity of the bicyclic pyrimidine nucleoside analogues against simian varicella virus (SVV) does not correlate with their substrate activity for SVV-encoded thymidine kinase.	2004-03-19	14985094
Penciclovir solubility in Eudragit films: a comparison of X-ray, thermal, microscopic and release rate techniques.	2004-03-10	15019028
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?	2004-03	15168799
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.	2004-02-17	15111272
Changing paradigms in dermatology: antivirals in dermatology.	2003-12-18	14678723
Comparison of [18F]FHBG and [14C]FIAU for imaging of HSV1-tk reporter gene expression: adenoviral infection vs stable transfection.	2003-11	14579096
Penciclovir cream--improved topical treatment for herpes simplex infections.	2003-10-16	15452407
Valacyclovir in the treatment of herpes simplex, herpes zoster, and other viral infections.	2003-09-25	14505192
Inhibition of sickling in vitro by three purine-based antiviral agents: an approach to the treatment of sickle cell disease.	2003-09-16	12972037
Profiling penciclovir susceptibility and prevalence of resistance of herpes simplex virus isolates across eleven clinical trials.	2003-09	14505088
Recurrent herpes simplex labialis: selected therapeutic options.	2003-09	12954137
Review of antiviral therapy for herpes labialis, genital herpes and herpes zoster.	2003-08	15482124
Generation of stable cell lines expressing Lamivudine-resistant hepatitis B virus for antiviral-compound screening.	2003-06	12760870
Optimization of cellular nucleotide extraction and sample preparation for nucleotide pool analyses using capillary electrophoresis.	2003-05-05	12668076
Brivudine: a herpes virostatic with rapid antiviral activity and once-daily dosing.	2003-05	12861349
Molecular imaging of protein-protein interactions: controlled expression of p53 and large T-antigen fusion proteins in vivo.	2003-04-15	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.	2003-04-15	12696003
MicroPET imaging of prostate cancer in LNCAP-SR39TK-GFP mouse xenografts.	2003-04-01	12640659
The role of stratum corneum and dermal microvascular perfusion in penetration and tissue levels of water-soluble drugs investigated by microdialysis.	2003-03	12653734
Novel agents and strategies to treat herpes simplex virus infections.	2003-02	12556212
In vitro activity of potential anti-poxvirus agents.	2003-01	12615301
Herpes simplex virus resistance to antiviral drugs.	2003-01	12589832
Current and potential therapies for the treatment of herpes-virus infections.	2003	12790345
[4'-Thio-5-ethyl-2'-deoxyuridine 5'-phosphonates: synthesis and antiviral activity].	2002-11-01	12408030
Antiviral agents: Non-antiretroviral [correction of Nonantiviral] drugs.	2002-10	12271305
Studies on the thermal decomposition process and kinetics of purine drugs.	2002-08	12567782
Ganciclovir and penciclovir, but not acyclovir, induce apoptosis in herpes simplex virus thymidine kinase-transformed baby hamster kidney cells.	2001-05	12959326
In vitro activities of penciclovir and acyclovir against herpes simplex virus types 1 and 2.	1992-09	1329640

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