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| Pronunciation | /ˌpɛnˈsaɪkloʊˌvɪər/[1] |
| Trade names | Denavir |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a697027 |
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| Routes of administration | Topical |
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| Pharmacokinetic data | |
| Bioavailability | 1.5% (oral), negligible (topical) |
| Protein binding | <20% |
| Metabolism | Viral thymidine kinase |
| Eliminationhalf-life | 2.2–2.3 hours |
| Excretion | Kidney |
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| ECHA InfoCard | 100.189.687 |
| Chemical and physical data | |
| Formula | C10H15N5O3 |
| Molar mass | 253.262 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 275 to 277 °C (527 to 531 °F) |
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Penciclovir is aguanosine analogueantiviral medication used for the treatment of variousherpesvirus infections. It is anucleoside analogue which exhibits low toxicity and good selectivity. It is used as atopical treatment. It is sold under the brand nameDenavir among others.
Penciclovir was approved for medical use in 1996.[3]
Inherpes labialis, the duration of healing, pain and detectable virus is reduced by up to one day,[4] compared with the total duration of 2–3 weeks of disease presentation.
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Penciclovir is inactive in its initial form. Within a virally infected cell a viralthymidine kinase adds aphosphate 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 viralDNA polymerase, thus impairing the ability of the virus to replicate within the cell.
The selectivity of penciclovir may be attributed to two factors. First, cellular thymidine kinases phosphorylate 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. Second, the activated drug binds to viral DNA polymerase with a much higher affinity than to human DNA polymerases. As a result, penciclovir exhibits negligiblecytotoxicity to healthy cells.
The structure and mode of action of penciclovir are very similar to that of other nucleoside analogues, such as the more widely usedaciclovir. 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 higher given equivalent cellular doses.[citation needed]
