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{{drugbox
__NOTOC__
| IUPAC_name = 2-amino-9-<nowiki>[</nowiki>4-hydroxy-3-(hydroxymethyl)butyl<nowiki>]</nowiki>-<br />3''H''-purin-6-one
{{Penciclovir}}
| image = Penciclovir.png
{{CMG}}
| width = 150
 
| CAS_number = 39809-25-1
==Overview==
| ATC_prefix = D06
| ATC_suffix = BB06
| ATC_supplemental = {{ATC|J05|AB13}}
| PubChem = 4725
| DrugBank = APRD00041
| C=10 | H=15 | N=5 | O=3
| molecular_weight = 253.258 g/mol
| bioavailability = 1.5% (oral), negligible (topical)
| protein_bound = <20%
| metabolism = Viral thymidine kinase
| elimination_half-life = 2.2–2.3 hours
| excretion = Renal
| pregnancy_category = B1 <small>([[Australia|Au]])</small>, B <small>([[United States|U.S.]])</small>
| legal_status = S2 <small>(Au)</small>
| routes_of_administration = Topical
}}
'''Penciclovir''' ([[International Nonproprietary Name|INN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[pɛnˈsaɪklovir]}}) is a [[guanine analogue]] [[antiviral drug]] used for the treatment of various [[herpesvirus]] infections. It is a [[Nucleoside_analogues|nucleoside analogue]] which exhibits low toxicity and good selectivity. Because penciclovir is absorbed poorly when given orally (by mouth) it is used more as a topical treatment, and is the active ingredient in the cold sore medications Denavir and Fenistil. [[Famciclovir]] is a [[prodrug]] of penciclovir with improved oral bioavailability.
'''Penciclovir''' ([[International Nonproprietary Name|INN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[pɛnˈsaɪklovir]}}) is a [[guanine analogue]] [[antiviral drug]] used for the treatment of various [[herpesvirus]] infections. It is a [[Nucleoside_analogues|nucleoside analogue]] which exhibits low toxicity and good selectivity. Because penciclovir is absorbed poorly when given orally (by mouth) it is used more as a topical treatment, and is the active ingredient in the cold sore medications Denavir and Fenistil. [[Famciclovir]] is a [[prodrug]] of penciclovir with improved oral bioavailability.


==Mode of action and selectivity==
==Category==
Penciclovir is inactive in its initial form. Within a virally infected cell a viral [[thymidine kinase]] adds a [[phosphate]] group to the penciclovir molecule; this is the rate-limiting step in the activation of penciclovir. Cellular (human) [[kinase]]s then add two more phosphate groups, producing the active penciclovir triphosphate. This activated form inhibits viral [[DNA polymerase]], thus impairing the ability of the virus to replicate within the cell.
Anticiral
 
==US Brand Names==
DENAVIR<sup>®</sup>
 


The [[selective toxicity|selectivity]] of penciclovir may be attributed to two factors. Firstly, cellular thymidine kinases phosphoylate the parent form significantly less rapidly than does the viral thymidine kinase, so the active triphosphate is present at much higher concentrations in virally infected cells than in uninfected cells. Secondly, the activated drug binds to viral DNA polymerase with a much higher affinity than to human DNA polymerases. As a result penciclovir exhibits negligible [[cytotoxicity]] to healthy cells.
==FDA Package Insert==


The structure and mode of action of penciclovir is very similar to that of other nucleoside analogues such as the more widely used [[aciclovir]]. A difference between aciclovir and penciclovir is that the active triphosphate form of penciclovir persists within the cell for a much longer time than the activated form of aciclovir, so the concentration within the cell of penciclovir will be relatively higher given equivalent cellular doses.
'''  [[Penciclovir description|Description]]'''
'''| [[Penciclovir clinical pharmacology|Clinical Pharmacology]]'''
'''| [[Penciclovir microbiology|Microbiology]]'''
'''| [[Penciclovir indications and usage|Indications and Usage]]'''
'''| [[Penciclovir contraindications|Contraindications]]'''
'''| [[Penciclovir warnings and precautions|Warnings and Precautions]]'''
'''| [[Penciclovir adverse reactions|Adverse Reactions]]'''
'''| [[Penciclovir drug interactions|Drug Interactions]]'''
'''| [[Penciclovir overdosage|Overdosage]]'''
'''| [[Penciclovir clinical studies|Clinical Studies]]'''
'''| [[Penciclovir dosage and administration|Dosage and Administration]]'''
'''| [[Penciclovir how supplied|How Supplied]]'''
'''| [[Penciclovir labels and packages|Labels and Packages]]'''


{{antimicrobial-stub}}
==Mechanism of Action==


[[Category:Antivirals]]
==References==
{{Antibiotics and chemotherapeutics for dermatological use}}
{{Reflist|2}}
{{Antivirals}}


[[de:Penciclovir]]
[[Category:Antibiotics]]
{{WikiDoc Sources}}
[[Category:Wikinfect]]

Revision as of 15:00, 6 January 2014

Penciclovir
DENAVIR® FDA Package Insert
Description
Clinical Pharmacology
Microbiology
Indications and Usage
Contraindications
Warnings and Precautions
Adverse Reactions
Drug Interactions
Overdosage
Dosage and Administration
Labels and Packages

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Penciclovir (INN) (IPA: Template:IPA) is a guanine analogue antiviral drug used for the treatment of various herpesvirus infections. It is a nucleoside analogue which exhibits low toxicity and good selectivity. Because penciclovir is absorbed poorly when given orally (by mouth) it is used more as a topical treatment, and is the active ingredient in the cold sore medications Denavir and Fenistil. Famciclovir is a prodrug of penciclovir with improved oral bioavailability.

Category

Anticiral

US Brand Names

DENAVIR®


FDA Package Insert

Description | Clinical Pharmacology | Microbiology | Indications and Usage | Contraindications | Warnings and Precautions | Adverse Reactions | Drug Interactions | Overdosage | Clinical Studies | Dosage and Administration | How Supplied | Labels and Packages

Mechanism of Action

References