Valganciclovir hydrochloride

Base Information

• Chemical Name: Valganciclovir hydrochloride
• CAS No.: 175865-59-5
• Molecular Formula: C14H23ClN6O5
• Molecular Weight: 390.827
• Hs Code.: 2933595960
• Mol file: 175865-59-5.mol

Synonyms:L-Valine,2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester,monohydrochloride (9CI);RS 079070-194;Ro 107-9070/194;Valcyte;

Chemical Property of Valganciclovir hydrochloride

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 1.08E-16mmHg at 25°C
• Melting Point: 162-164°C
• Boiling Point: 629.1 °C at 760 mmHg
• Flash Point: 334.3 °C
• PSA: 171.37000
• LogP: 0.64680
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: H2O: ≥8mg/mL

Purity/Quality:

≥95% ^*data from raw suppliers

Valganciclovir Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Valganciclovir hydrochloride, a prodrug of the antiviral ganciclovir, was launched in the US for the oral treatment of cytemegalovirus (CMV) retinitis, a sight-threatening complication in patients with AIDS. This L-Valyl ester prodrug can be prepared in three steps from the nucleoside analog ganciclovir by trimethylsilyl-protection of the amino group, coupling with N-benzyloxycarbonyl-L-valine-N-carboxyanhydride, hydrolysis with hydrochloric acid and hydrogenolysis of the Cbz-protecting group. Valganciclovir is well absorbed and rapidly hydrolyzed to ganciclovir by intracellular esterases in the intestinal mucosal cells and by hepatic esterases. Unlike ganciclovir, valganciclovir was demonstrated to be actively transported by the intestinal peptide transporter PEPT1 in Caco-2 cells. As a consequence, its absolute bioavailability in human was 10-fold higher compared to ganciclovir (6%). In clinical trials, it was shown that a twice-daily 900 mg dose of valganciclovir resulted in similar systemic ganciclovir exposure to 5 mg/kg twice-daily intravenous injection of ganciclovir. Valganciclovir concentrations could not be quantified in most patients within three to four hours. In a randomized non-blind phase III clinical trial, oral valganciclovir (900 mg twice daily for three weeks then 900 mg once daily for one week) was as effective as intravenous ganciclovir (5 mg/kg twice daily for three weeks then 5 mg/kg once daily). Oral treatment with valganciclovir avoided catheter-related infection that sometimes occurred with intravenous ganciclovir.
• Uses: Valganciclovir hydrochloride hydrate may be used in HIV-related cell signaling studies. A pro-drug of ganciclovir. Used in treatment of retro-virus antibacterial, inhibits protein synthesis Valganciclovir is the valyl ester prodrug of ganciclovir , an antiviral agent used for the treatment of HIV associated retinitis and for the prevention of post transplant cytomegalovirus (CMV) infections. Upon oral administration, intestinal and hepatic esterases rapidly convert valganciclovir to ganciclovir, which can inhibit viral DNA synthesis (IC50 = 0.95 μM) by targeting the CMV polymerase.

Technology Process of Valganciclovir hydrochloride

There total 19 articles about Valganciclovir hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.4%

C14H22N6O5*C2HF3O2 → valganciclovir hydrochloride (175865-59-5)

Guidance literature:

With hydrogenchloride; In water; acetone; at 10 - 25 ℃; for 3h;

Reference yield: 88.0%

(2S)-2-((2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy)-3-(benzyloxy)propyl-2-(benzyloxycarbonylamino)-3-methylbutanoate (175865-55-1) → valganciclovir hydrochloride (175865-59-5)

Guidance literature:

With hydrogenchloride; hydrogen; 5%-palladium/activated carbon; In methanol; water; under 5171.62 - 7757.43 Torr; Inert atmosphere;

Reference yield: 82.0%

2-(2-amino-1,6 dihydro-6-oxo-purine-9-yl)-methoxy-3-hydroxy-1-propyl-N-(benzyloxy carbonyl)-L-valinate (194154-40-0) → valganciclovir hydrochloride (175865-59-5)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; hydrogen; In methanol; water; at 20 ℃; for 18h; under 1500.15 Torr;

upstream raw materials:

2-(2-amino-1,6 dihydro-6-oxo-purine-9-yl)-methoxy-3-hydroxy-1-propyl-N-(benzyloxy carbonyl)-L-valinate

L-valine

O-mesyl ganciclovir

2-[(2-amino-1,6-dihydro-6-oxopurin-9-yl)methyloxy]-3-hydroxypropyl 2'-(S)-azido-3'-methylbutanoate

Refernces

• 1、 -. "Preparation method of valganciclovir hydrochloride". . . Retrieved 2020/10/21.
• 2、 -. "PROCESS FOR THE PREPARATION OF 2-AMINO-9-((2-PHENYL-1,3-DIOXAN-5-YLOXY)METHYL)-1H-PURIN-6(9H)-ONE COMPOUND USEFUL IN THE PREPARATION OF VALGANCICLOVIR". Page/Page column 10. . Retrieved 2013/02/28.