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Encyclopedia > Penciclovir
Penciclovir chemical structure
Penciclovir
Systematic name
IUPAC name
2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-
3H-purin-6-one
Identifiers
CAS number 39809-25-1
ATC code D06BB06 J05AB13
PubChem 4725
DrugBank APRD00041
Chemical data
Formula C10H15N5O3 
Mol. weight 253.258 g/mol
Pharmacokinetic data
Bioavailability 1.5% (oral), negligible (topical)
Protein binding <20%
Metabolism Viral thymidine kinase
Half life 2.2–2.3 hours
Excretion Renal
Therapeutic considerations
Pregnancy cat. B1 (Au), B (U.S.)
Legal status S2 (Au)
Routes Topical

Penciclovir (INN) (IPA: [pɛnˈsaɪklovir]) 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. Famciclovir is a prodrug of penciclovir with improved oral bioavailability. IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... You may be looking for albumen, or egg white. ... Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)) is the biochemical modification of chemical compounds in living organisms anggjgjhnd cell (b). ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother. ... Motto: none (formerly Advance Australia) Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official language(s) English (de facto)1 Government Const. ... Motto: (historic) In God We Trust (official, 1956–present) Anthem: The Star-Spangled Banner Capital Washington, D.C. Largest city New York Official language(s) None at federal level; English de facto Government Federal Republic  - President George W. Bush (R)  - Vice President Dick Cheney (R) Independence - Declared - Recognized From Great... The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... The International Phonetic Alphabet (IPA) is a system of phonetic notation devised by linguists to accurately and uniquely represent each of the wide variety of sounds (phones or phonemes) used in spoken human language. ... Antiviral drugs are a class of medication used specifically for treating viral infections. ... Genera Subfamily Alphaherpesvirinae    Simplexvirus    Varicellovirus    Mardivirus    Iltovirus Subfamily Betaherpesvirinae    Cytomegalovirus    Muromegalovirus    Roseolovirus Subfamily Gammaherpesvirinae    Lymphocryptovirus    Rhadinovirus Unassigned    Ictalurivirus The Herpesviridae are a family of DNA viruses that cause diseases in humans and animals. ... Nucleoside analogues are a range of antiviral products used to prevent viral replication in infected cells. ... Famciclovir is an antiviral medicine that stops the varicella zoster virus that causes shingles. ... A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ...


Mode of action and selectivity

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) kinases 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. Thymidine kinase TK, is an enzyme, a phosphotransferase (a kinase): 2-deoxythymidine kinase, ATP-thymidine 5-phosphotransferase, {{{EC 2. ... In inorganic chemistry, a phosphate is a salt of phosphoric acid. ... In biochemistry, a kinase is a type of enzyme that transfers phosphate groups from high-energy donor molecules, such as ATP, to specific target molecules (substrates); the process is termed phosphorylation. An enzyme that removes phosphate groups from targets is known as a phosphatase. ... 3D structure of the DNA-binding helix-hairpin-helix motifs in human DNA polymerase beta A DNA polymerase is an enzyme that assists in DNA replication. ...


The 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. Cytotoxicity is the quality of being poisonous to cells. ...


The structure and mode of action of penciclovir is very similar to that of other nucleoside analgues 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. Aciclovir (INN) (IPA: ) or acyclovir (USAN), marketed as Zovirax, is one of the main antiviral drugs. ...



Antivirals (ATC J05A) edit
Anti-herpesvirus agents   Aciclovir · Cidofovir · Docosanol · Famciclovir · Foscarnet · Fomivirsen · Ganciclovir · Idoxuridine · Penciclovir · Trifluridine · Tromantadine · Valaciclovir · Valganciclovir · Vidarabine
Anti-influenza agents Amantadine · Oseltamivir · Peramivir · Rimantadine · Zanamivir
 
Antiretroviral drugs   NRTIs Zidovudine · Didanosine · Stavudine · Zalcitabine · Lamivudine · Abacavir · Tenofovir · Emtricitabine
NNRTIs   Nevirapine · Efavirenz · Delavirdine
NtRTIs   Tenofovir · Adefovir
PIs Saquinavir · Indinavir · Atazanavir · Ritonavir · Nelfinavir · Amprenavir · Fosamprenavir · Lopinavir · Tipranavir · Darunavir
 
Other antiviral agents Fomivirsen · Enfuvirtide · Imiquimod · Interferon · Ribavirin · Viramidine

  Results from FactBites:
 
Herpesviruses 2000: Penciclovir (581 words)
Penciclovir is a nucleoside deoxyguanosine analog that inhibits the DNA synthesis of herpesviruses.
Penciclovir triphosphate is now free to insert in the viral DNA as it is being formed in place of the nucleotide guanine and terminate the sequence, thus inhibiting replication of the virus.
Intravenous penciclovir is not currently licensed as a treatment, but in clinical trials it was found that doses of 5mg per kg every twelve hours was as effective as acyclovir in treating HSV infections.
MedlinePlus Drug Information: Penciclovir Cream (497 words)
Penciclovir is used on the lips and faces of adults to treat cold sores caused by herpes simplex virus.
Penciclovir does not cure herpes infections but decreases pain and itching if applied when the earliest symptoms first appear.
Penciclovir should only be used on the lips and face.
  More results at FactBites »

 
 

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