Valganciclovir HCl , ≥99% , 175865-59-5

Synonym(s):
L-Valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester monohydrochloride;2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate hydrochloride hydrate;L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester, monohydrochloride hydrate;Valganciclovir hydrochloride hydrate

CAS NO.：175865-59-5

Empirical Formula: C14H23ClN6O5

Molecular Weight: 390.82

MDL number: MFCD08460118

EINECS: 641-360-4

PRODUCT Properties

• Melting point: 162-164°C
• storage temp.: Keep in dark place,Inert atmosphere,2-8°C
• solubility: H2O: ≥8mg/mL
• form: powder
• color: white to tan
• Stability: Hygroscopic
• InChIKey: ZORWARFPXPVJLW-MTFPJWTKSA-N

Description and Uses

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.

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.

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H302-H312-H332
• Precautionary statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501
• WGK Germany: 3
• HS Code: 2933595960