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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/08/03 23:07:58」(JST)
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Penciclovir
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Systematic (IUPAC) name |
2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1H-purin-6(9H)-one
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Clinical data |
Trade names |
Denavir |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a697027 |
Pregnancy
category |
- AU: B1
- US: B (No risk in non-human studies)
|
Legal status |
- AU: Pharmacy Only (S2)
- US: ℞-only
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Routes of
administration |
Topical |
Pharmacokinetic data |
Bioavailability |
1.5% (oral), negligible (topical) |
Protein binding |
<20% |
Metabolism |
Viral thymidine kinase |
Biological half-life |
2.2–2.3 hours |
Excretion |
Renal |
Identifiers |
CAS Registry Number |
39809-25-1 Y |
ATC code |
D06BB06 J05AB13 |
PubChem |
CID: 4725 |
DrugBank |
DB00299 Y |
ChemSpider |
4563 Y |
UNII |
359HUE8FJC Y |
KEGG |
D05407 Y |
ChEBI |
CHEBI:7956 Y |
ChEMBL |
CHEMBL1540 Y |
Chemical data |
Formula |
C10H15N5O3 |
Molecular mass |
253.258 g/mol |
SMILES
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O=C2/N=C(\Nc1n(cnc12)CCC(CO)CO)N
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InChI
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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) Y
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Key:JNTOCHDNEULJHD-UHFFFAOYSA-N Y
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Y (what is this?) (verify) |
Penciclovir (INN) is a guanosine 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 (NDC 0135-0315-52), Vectavir and Fenivir. Famciclovir is a prodrug of penciclovir with improved oral bioavailability.
Contents
- 1 Efficacy
- 2 Mode of action and selectivity
- 3 See also
- 4 References
Efficacy
In herpes labialis, the duration of healing, pain and detectable virus is reduced by up to one day,[1] compared with the total duration of 2–3 weeks of disease presentation.
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.
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 negligible cytotoxicity 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 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 higher given equivalent cellular doses.
See also
- Nucleoside analogue
- Famciclovir
References
- ^ Farmaceutiska Specialiteter i Sverige - the Swedish official drug catalog. [http://www.fass.se Fass.se --> Vectavir. Retrieved on August 12, 2009. Translated from "Tiden för läkning, smärta och påvisbart virus förkortas med upp till ett dygn."
Antibiotics and chemotherapeutics for dermatological use (D06)
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Antibiotics |
Tetracycline and derivatives
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- Demeclocycline
- Chlortetracycline
- Oxytetracycline
- Tetracycline
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Others
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- Amphenicol: Chloramphenicol
- Aminoglycosides: Neomycin
- Gentamicin
- Amikacin
- Streptogramin: Virginiamycin
- other: Fusidic acid
- Bacitracin
- Tyrothricin
- Mupirocin
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|
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Chemotherapeutics |
Sulfonamides
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- Silver sulfadiazine
- Sulfathiazole
- Mafenide
- Sulfamethizole
- Sulfanilamide
- Sulfamerazine
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Antivirals
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- Aciclovir
- Penciclovir
- Idoxuridine
- Edoxudine
- Imiquimod
- Resiquimod
- Podophyllotoxin
- Docosanol
- Tromantadine
- Inosine
- Lysozyme
- Ibacitabine
- Lysine
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Other
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- Ingenol mebutate
- Metronidazole
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Index of skin
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Description |
- Anatomy
- Physiology
- Development
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Disease |
- Infections
- Vesiculobullous
- Dermatitis and eczema
- Papulosquamous
- Urticaria and erythema
- Radiation-related
- Pigmentation
- Mucinoses
- Keratosis, ulcer, atrophy, and necrobiosis
- Vasculitis
- Fat
- Neutrophilic and eosinophilic
- Congenital
- Neoplasms and cancer
- nevi and melanomas
- epidermis
- dermis
- Symptoms and signs
- Terminology
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Treatment |
- Procedures
- Drugs
- antibiotics
- disinfectants
- emollients and protectives
- itch
- psoriasis
- other
- Wound and ulcer
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DNA virus antivirals (primarily J05, also S01AD and D06BB)
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Baltimore I |
Herpesvirus |
DNA-synthesis
inhibitor |
TK activated |
Purine analogue |
- guanine (Aciclovir#/Valaciclovir
- Ganciclovir/Valganciclovir
- Penciclovir/Famciclovir)
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|
Pyrimidine analogue |
- uridine (Idoxuridine
- Trifluridine
- Edoxudine)
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Not TK activated |
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Other |
- Docosanol
- early protein (Fomivirsen)
- Tromantadine
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HPV/MC |
- Imiquimod/Resiquimod
- Podophyllotoxin
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Vaccinia |
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Poxviridae |
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Hepatitis B (VII) |
- Nucleoside analogues/NARTIs: Entecavir
- Lamivudine
- Telbivudine
- Clevudine
- Nucleotide analogues/NtRTIs: Adefovir
- Tenofovir
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Multiple/general |
Nucleic acid inhibitors |
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Interferon |
- Interferon alfa 2b
- Peginterferon alfa-2a
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Multiple/unknown |
- Ribavirin#/Taribavirin†
- Moroxydine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of viral disease
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Description |
|
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Disease |
- Systemic
- Cutaneous
- Zoster
- Human papillomavirus
- Zoonotic
- Symptoms and signs
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Treatment |
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UpToDate Contents
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English Journal
- Ribavirin Inhibits Human Parainfluenza Virus type 2 Replication in vitro.
- Kihira S1, Uematsu J, Kawano M, Itoh A, Ohkouchi A, Satoh S, Maeda Y, Sakai K, Yamamoto H, Tsurudome M, O'Brien M, Komada H.
- Microbiology and immunology.Microbiol Immunol.2014 Aug 25. doi: 10.1111/1348-0421.12192. [Epub ahead of print]
- The antiviral activities of eight nucleoside analog antiviral drugs (ribavirin, acyclovir, lamivudine, 3'-azido-3'-deoxythymidine, emtricitabine, tenofovir, penciclovir and ganciclovir) against human parainfluenza virus type 2 (hPIV-2) were investigated. Only ribavirin (RBV) inhibited both cell fusi
- PMID 25154465
- Single nucleotide polymorphisms of thymidine kinase and DNA polymerase genes in clinical herpes simplex virus type 1 isolates associated with different resistance phenotypes.
- Schubert A1, Gentner E2, Bohn K3, Schwarz M3, Mertens T1, Sauerbrei A4.
- Antiviral research.Antiviral Res.2014 Jul;107:16-22. doi: 10.1016/j.antiviral.2014.03.015. Epub 2014 Apr 18.
- The role of mutations in the thymidine kinase (TK, UL23) and DNA polymerase (pol, UL30) genes of herpes simplex virus (HSV) for development of different resistance phenotypes has to be exactly determined before genotypic resistance testing can be implemented in patient's care. Furthermore, the occur
- PMID 24747042
- Testing the sensitivities of noncognate inhibitors to varicella zoster virus thymidine kinase: implications for postherpetic neuralgia therapy with existing agents.
- Yang L1, Mo X, Yang H, Dai H, Tan F.
- Journal of molecular modeling.J Mol Model.2014 Jul;20(7):2321. doi: 10.1007/s00894-014-2321-6. Epub 2014 Jun 25.
- Varicella zoster virus (VZV), a member of the human herpesvirus family, affects peripheral or cranial nerves and can reactivate years after the primary infection. Thymidine kinase (TK) is essential for VZV replication, and its active site is highly conserved in the herpesvirus family. A number of sm
- PMID 24961898
Japanese Journal
- Characterization of DNA Polymerase-Associated Acyclovir-Resistant Herpes Simplex Virus Type 1: Mutations, Sensitivity to Antiviral Compounds, Neurovirulence, and In-Vivo Sensitivity to Treatment
- Wang Li-Xin,Takayama-Ito Mutsuyo,Kinoshita-Yamaguchi Hitomi [他],Kakiuchi Satsuki,Suzutani Tatsuo,Nakamichi Kazuo,Lim Chang-Kweng,Kurane Ichiro,Saijo Masayuki
- Japanese Journal of Infectious Diseases 66(5), 404-410, 2013
- … DNApol-associated ACVr clones showed cross-resistance to foscarnet, penciclovir, and vidarabine but were sensitive or hypersensitive to GCV, brivudin, sorivudine, and spongothymidine. …
- NAID 130003381717
- Pharmacology: Pharmacokinetics of penciclovir after oral administration of its prodrug famciclovir to horses
- Tsujimura Koji,Yamada Masayuki,Nagata Shun-ichi [他]
- 日本獣醫學会会誌 72(3), 357-361, 2010-03
- NAID 40017040224
- Pharmacokinetics of Penciclovir after Oral Administration of its Prodrug Famciclovir to Horses
- TSUJIMURA Koji,YAMADA Masayuki,NAGATA Shun-ichi,YAMANAKA Takashi,NEMOTO Manabu,KONDO Takashi,KUROSAWA Masahiko,MATSUMURA Tomio
- Journal of Veterinary Medical Science 72(3), 357-361, 2010
- … We investigated the pharmacokinetics of penciclovir after oral administration of its prodrug famciclovir to horses. … Following an oral dose of famciclovir at 20 mg/kg, maximum plasma concentrations of penciclovir occurred between 0.75 and 1.5 hr (mean 0.94 ± 0.38 hr) after dosing and were in the range 2.22 to 3.56 μg/ml (mean 2.87 ± 0.61 μg/ml). … The concentrations of penciclovir declined in a biphasic manner after the peak concentration was attained. …
- NAID 130000134548
Related Links
- ... Denavir® (penciclovir cream, 1%) can help them heal when they do reappear. 4 4. Denavir (penciclovir cream, 1%) Prescribing Information. Cranford, NJ: New American Therapeutics, Inc. December 2010. Denavir cream 4 ...
- Keep all appointments with your doctor. Penciclovir should only be used on the lips and face. Avoid getting it in your eyes. Keep the infected area clean and dry. Do not let anyone else use your medication. Ask your ...
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