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Penciclovir

Names

[ CAS No. ]:
39809-25-1

[ Name ]:
Penciclovir

[Synonym ]:
Fenistil
Vectavir
peniciclovir
Penciclovirum
9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine
2-Amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6H-purin-6-one
2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1,9-dihydro-6H-purin-6-one
Penciclovir
Adenovir
6H-Purin-6-one, 2-amino-3,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]-
UNII-359HUE8FJC
Denavir
2-Amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6H-purin-6-one,BRL-39123
2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1H-purin-6-one
2-AMINO-9-[4-HYDROXY-3-(HYDROXYMETHYL)BUTYL]-3,9-DIHYDROPURIN-6-ONE,CERTIFIED REFERENCE MATERIAL
MFCD00866931
2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3H-purin-6-one
Pencyclovir
9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine
2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydropurin-6-one
Famciclovir Impurity 4

Biological Activity

[Description]:

Penciclovir is reported to be potent against HSV types 1 and 2 with IC50 of 0.04-1.8 μg/mL and 0.06-4.4 μg/mL, respectively.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HSV
Research Areas >> Infection

[Target]

IC50: 0.04-1.8 μg/mL (HSV-1), 0.06-4.4 μg/mL (HSV-2), 1.6-8 μg/mL (VZV), 1.5-3.1 μg/mL (EBV), 51 μg/mL (HCMV)[1]


[In Vitro]

Penciclovir inhibits herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2), varicella-zoster virus (VZV), epstein-Barr virus (EBV), human cytomegalovirus (HCMV) with IC50 of 0.04-1.8 μg/mL, 0.06-4.4 μg/mL,1.6-8 μg/mL, 1.5-3.1 μg/mL, 51 μg/mL, respectively. Penciclovir (PCV) is an acyclic guanine derivative (which is not commercially available as an oral agent), has a spectrum of activity and a mechanism of action similar to those of acyclovir (ACV)[1].

[Cell Assay]

Human breast cancer cell lines MCF-7 and MDA-MB-435, glioblastoma U87MG, and embryonic kidney cells 293T are cultured at 37°C in a humidified atmosphere containing 5% CO2 in Iscove’s modified Dulbecco medium or Leibovitz’s L-medium and 5% fetal bovine serum (FBS). The assays are performed with slight modifications. In brief, cells are seeded into 24-well plates (5×104 cells/well) and infected 48 h later with 103 particles per cell of unmodified virus (Adtk), PEGylated virus (PEG-Adtk), or RGD-PEG-modified virus (RGD-PEG-Adtk) in triplicates in culture medium with 2% FBS and incubated for 4 h at 37°C. The incubation medium is then replaced by normal medium and cells are further incubated for 48 h. Cells are harvested and lysed with 500 μL of TK lysis buffer that contained 0.5% Nonidet P-40 (NP-40), 20 mM N-(2-hydroxyethyl) piperazine-N′-(2-ethanesulfonic acid) (HEPES) (pH 7.6), 2 mM Mg(OAc)2, 1 mM dithiothreitol, and 50 μM thymidine. The supernatant is collected after centrifugation. The samples are kept at -80°C until use. The modified and unmodified adenovirus protein concentrations are determined by the Micro BCA assay. One microgram of cell extract is incubated with HSV1-tk substrate 8-3H-Penciclovir (8-3 H-PCV). The phosphorylated tracer is separated from unphosphorylated 8-3 H-PCV with DE-81 filters. TK activity is expressed as the percentage of conversion of substrate per minute per microgram protein[2].

[References]

[1]. Piret J, et al. Resistance of herpes simplex viruses to nucleoside analogues: mechanisms, prevalence, and management. Antimicrob Agents Chemother. 2011 Feb;55(2):459-72.

[2]. Xiong Z, et al. Imaging chemically modified adenovirus for targeting tumors expressing integrin alphavbeta3 in living micewith mutant herpes simplex virus type 1 thymidine kinase PET reporter gene. J Nucl Med. 2006 Jan;47(1):130-9.


[Related Small Molecules]

Vidarabine | BAY 57-1293 | Acyclovir | idoxuridine | Valacyclovir hydrochloride | Amenamevir | Fiacitabine | 1-Docosanol | Tromantadine | B220 | BRL44385

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
636.7±65.0 °C at 760 mmHg

[ Melting Point ]:
275-277°C

[ Molecular Formula ]:
C10H15N5O3

[ Molecular Weight ]:
253.258

[ Flash Point ]:
338.9±34.3 °C

[ Exact Mass ]:
253.117493

[ PSA ]:
130.05000

[ LogP ]:
-3.58

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.749

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R10:Flammable.

[ Safety Phrases ]:
S16

[ RIDADR ]:
UN 1993 3/PG 3

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
3.2

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds