Valganciclovir hydrochloride CAS NO 175865-59-5
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175865-59-5 Valganciclovir hydrochloride Valganciclovir hydrochloride CAS NO 175865-59-5
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- Appearance:White powder
- Application:Pharmaceutical intermediates
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Valganciclovir hydrochloride CAS NO 175865-59-5
Details:
| Valganciclovir hydrochloride Basic information |
| Product Name: | Valganciclovir hydrochloride |
| Synonyms: | Valganciclovir-d5 HCl (Mixture of Diastereomers);Ro 107-9070/194;Rs 079070-194;Unii-4p3T9qf9nz;Valcyt;Valcyte;Valganciclovir hydrochlorid;Valganciclovir Hydrochloride (500 mg) |
| CAS: | 175865-59-5 |
| MF: | C14H23ClN6O5 |
| MW: | 390.82 |
| EINECS: | 641-360-4 |
| Product Categories: | Pharmaceuticals;CLEOCIN;API;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides |
| Mol File: | 175865-59-5.mol |
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| Valganciclovir hydrochloride Chemical Properties |
| Melting point | 162-164°C |
| storage temp. | Hygroscopic, -20°C Freezer, Under Inert Atmosphere |
| solubility | H2O: ≥8mg/mL |
| form | powder |
| color | white to tan |
| CAS DataBase Reference | 175865-59-5 |
| Safety Information |
| WGK Germany | 3 |
| Valganciclovir hydrochloride Usage And Synthesis |
| 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. |
| Chemical Properties | White Crystalline Solid |
| Originator | Roche (Switzerland) |
| Uses | A pro-drug of ganciclovir. Used in treatment of retro-virus |
| Uses | antibacterial, inhibits protein synthesis |
| Uses | 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. |
Valganciclovir hydrochloride CAS NO 175865-59-5
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