Name | Valaciclovir |
Synonyms | VALACYCLOVIR VALACICLOVIR Valaciclovir Valacyclovir-d4 VALACICLOVIR HCL VALACICLOVIR HYDROCHLORIDE l-valine 2-(guanin-9-ylmethoxy)ethyl ester L-Valine ester with 9-[(2-hydroxyethoxy)methyl]guanine L-VALINE 2-[(2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9YL)METHOXY]ETHYL ESTER L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester (9CI) L-VALINE 2-[(2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9YL)METHOXY]ETHYL ESTER, HYDROCHLORIDE SALT |
CAS | 124832-26-4 |
EINECS | 1312995-182-4 |
InChI | InChI=1/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1 |
Molecular Formula | C13H20N6O4 |
Molar Mass | 324.34 |
Density | 1.55±0.1 g/cm3(Predicted) |
pKa | 9.34±0.20(Predicted) |
Storage Condition | 2-8°C |
Use | Anti-Virus, for herpes Virus disease |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
valaciclovir hydrochloride: C13 H20 N604 .HCl. White or white crystalline powder, easy to absorb moisture, odorless and tasteless. The melting point was 150-152 °c. The maximum solubility in water is 174mg/mL at 25 °c. pK. 1.90, 7.47 and 9.43. UV absorption maximum (water):252 NM g8530).
L-valine was dissolved in a sodium hydroxide solution, and benzyl chloroformate and a sodium hydroxide solution were added dropwise for the reaction. After completion of the reaction, the reaction mixture was acidified with dilute hydrochloric acid, and then extracted with ethyl acetate. The extract was washed with sodium carbonate solution, and the washed solution was acidified, extracted, dried and concentrated to obtain an oily substance. The material was recrystallized from benzene to give N-benzyloxycarbonyl-L-valine. Acyclovir is dissolved in dimethylformamide, N-benzyloxycarbonyl-L-valine, 4,4-= methylaminopyridine and dicyclohexylcarbodiimide are added sequentially at a certain temperature, after completion of the reaction, insoluble matters were removed by filtration, and the filtrate was concentrated under reduced pressure and subjected to column chromatography. The obtained solid and 5% palladium-carbon were placed in methanol and tetrahydrofuran and hydrochloric acid solution, and subjected to catalytic hydrogenolysis, followed by filtration, concentration and recrystallization to obtain valacyclovir.
developed by Glaxo Well-come, Inc., USA, was first launched in the UK in 1995. Valaciclovir is the L-valine ester of acyclovir, a prodrug of acyclovir. For the treatment of varicella, herpes zoster and type I, Type II herpes simplex infection, including the initial and recurrent genital herpes.