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Details

Stereochemistry ACHIRAL
Molecular Formula C14H19N5O4
Molecular Weight 321.3318
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FAMCICLOVIR

SMILES

CC(=O)OCC(CCN1C=NC2=CN=C(N)N=C12)COC(C)=O

InChI

InChIKey=GGXKWVWZWMLJEH-UHFFFAOYSA-N
InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)

HIDE SMILES / InChI

Molecular Formula C14H19N5O4
Molecular Weight 321.3318
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
Selective activity of various antiviral compounds against HHV-7 infection.
1999 Aug
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.
1999 Dec
Evaluation of anti-herpesvirus activity of (1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]- guanine (A-5021) in mice.
1999 Jun
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.
1999 Jun 15
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
Recent advances in imaging endogenous or transferred gene expression utilizing radionuclide technologies in living subjects: applications to breast cancer.
2001
Acyclic/carbocyclic guanosine analogues as anti-herpesvirus agents.
2001 Apr-Jul
Antiviral drugs: current state of the art.
2001 Aug
Genetic risks of antiviral nucleoside analogues--a survey.
2001 Feb
Topical treatment of recurrent herpes labialis.
2001 Jan
Pediatric uses of valacyclovir, penciclovir and famciclovir.
2001 Nov
Separation methods for acyclovir and related antiviral compounds.
2001 Nov 25
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8.
2001 Nov-Dec
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
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
Viral diseases of the skin: diagnosis and antiviral treatment.
2002
Topical application of penciclovir cream for the treatment of herpes simplex facialis/labialis: a randomized, double-blind, multicentre, aciclovir-controlled trial.
2002 Jun
Changing paradigms in dermatology: antivirals in dermatology.
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
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
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
Drugs for non-HIV viral infections.
2005 Apr
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
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
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
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 21:26:30 GMT 2025
Edited
by admin
on Mon Mar 31 21:26:30 GMT 2025
Record UNII
QIC03ANI02
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FAMCICLOVIR
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
FAMVIR
Preferred Name English
FAMCICLOVIR [JAN]
Common Name English
2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propanediol diacetate (ester)
Common Name English
FAMCICLOVIR [MART.]
Common Name English
Famciclovir [WHO-DD]
Common Name English
1,3-PROPANEDIOL, 2-(2-(2-AMINO-9H-PURIN-9-YL)ETHYL)-, DIACETATE (ESTER)
Common Name English
BRL-42810
Code English
NSC-758921
Code English
FAMCICLOVIR [USP MONOGRAPH]
Common Name English
famciclovir [INN]
Common Name English
FAMCICLOVIR [USP-RS]
Common Name English
FAMCICLOVIR [MI]
Common Name English
FAMCICLOVIR [ORANGE BOOK]
Common Name English
FAMCICLOVIR [USAN]
Common Name English
FAMCICLOVIR [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AB09
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
WHO-ATC S01AD07
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
NDF-RT N0000020060
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
NDF-RT N0000180187
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
LIVERTOX NBK547978
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
WHO-VATC QS01AD07
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
WHO-VATC QJ05AB09
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
NCI_THESAURUS C29575
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
NCI_THESAURUS C281
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
NDF-RT N0000175459
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
Code System Code Type Description
MESH
C060590
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
MERCK INDEX
m5240
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C29044
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
EVMPD
SUB07501MIG
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
USAN
EE-84
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
HSDB
8121
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
CHEBI
4974
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
DAILYMED
QIC03ANI02
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
INN
6438
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
DRUG CENTRAL
1128
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PRIMARY
CAS
104227-87-4
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
NSC
758921
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
SMS_ID
100000092280
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
RXCUI
68099
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
FAMCICLOVIR
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
LACTMED
Famciclovir
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
DRUG BANK
DB00426
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
FDA UNII
QIC03ANI02
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
ChEMBL
CHEMBL880
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID0023038
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
RS_ITEM_NUM
1269152
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
PUBCHEM
3324
Created by admin on Mon Mar 31 21:26:30 GMT 2025 , Edited by admin on Mon Mar 31 21:26:30 GMT 2025
PRIMARY
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC