Name | Penciclovir |
Synonyms | PCV Vectavir BRL-39123 BRL-39123A Penciclovir Penciceovir PENCICLOVIR-D4 9-[4-hychoxy-3-(hydvoxymethyl)butyl]guanine 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydropurin-6-one 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydro-6H-purin-6-one 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]- |
CAS | 39809-25-1 |
EINECS | 663-371-3 |
InChI | InChI=1/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) |
Molecular Formula | C10H15N5O3 |
Molar Mass | 253.26 |
Density | 1.68±0.1 g/cm3(Predicted) |
Melting Point | 275-277°C |
Boling Point | 653.4±65.0 °C(Predicted) |
Flash Point | 348.9°C |
Solubility | Soluble in water (1.7 mg/ml) at 20 °C, DMSO, and aqueous buffer. |
Vapor Presure | 5.81E-18mmHg at 25°C |
Appearance | White solid |
Color | White to Off-White |
Maximum wavelength(λmax) | ['253nm(H2O)(lit.)'] |
Merck | 14,7083 |
pKa | 14.42±0.10(Predicted) |
Storage Condition | Keep in dark place,Sealed in dry,Store in freezer, under -20°C |
Sensitive | Sensitive to heat |
Refractive Index | 1.748 |
MDL | MFCD15142866 |
Physical and Chemical Properties | Melting point 275-277°C |
Use | Antiviral drugs for the treatment of herpes labialis and genital herpes |
In vitro study | Penciclovir is a guanine analog antiviral drug used to treat infections with various herpes viruses. It is a nucleoside analog with low toxicity and good selectivity. Penciclovir is a selective anti-herpesvirus drug, especially for herpes simplex virus type I and II (HSV-1 and HSV-2) and varicella zoster virus (VZV). Penciclovir is converted into its active form, Penciclovir triphosphate, by a cellular kinase. It competes with deoxyguanosine triphosphate to inhibit viral DNA polymerase. It inhibits DNA synthesis in virus-infected cells. Penciclovir has in vitro activity against herpes simplex virus type I (HSV-1) and type II (HSV-2) without inhibiting the synthesis of DNA in uninfected cells. Antiviral effects are exerted by qualitative changes in viral thymidine kinase or DNA polymerase. The study of herpes simplex virus type I showed that Penciclovir induced apoptosis without causing too much genotoxicity. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36 - Irritating to the eyes |
Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
RTECS | UP0789400 |
2,2 dimethyl 5-(2 bromoethyl)-1,3 dioxane is dissolved in dimethylformamide, 2-amino -6-chloropurine and potassium carbonate are added sequentially at room temperature, the reaction was carried out at 40 ℃ for a certain time, and the obtained alkylated product was hydrolyzed with hydrochloric acid at a certain temperature to obtain penciclovir.
developed by Smith Kline Beecham, UK, was launched in the UK in 1996. Nucleoside anti Virus drugs, in vitro type I and Type II Herpes Sinplex Virus Virus inhibitory effect, in Virus of infected cells, Virus thymidine kinase will be phosphorylated into penciclovir monophosphate, the cellular kinase then converts penciclovir monophosphate to penciclovir triphosphate. In vitro experiments showed that penciclovir triphosphate and deoxyguanosine triphosphate competitively inhibited Herpes Sinplex Virus polyvinylidene, thereby selectively inhibiting Herpes Sinplex Virus of DNA synthesis and inhibition.