ChemicalBook--->CAS DataBase List--->175865-59-5

175865-59-5

175865-59-5 Structure

175865-59-5 Structure
IdentificationBack Directory
[Name]

Valganciclovir hydrochloride
[CAS]

175865-59-5
[Synonyms]

Valcyt
Valcyte
Rs 079070-194
Unii-4p3T9qf9nz
Ro 107-9070/194
VALGANCICLOVIR HCL
Valganciclovir hydrochlorid
VALGANCICLOVIR HYDROCHLORIDE
Valganciclovir hydrochloride hydrate
Valganciclovir Hydrochloride (500 mg)
2-[(2-AMino-1,6-dihydro-6-oxo-9H-purin-9-yl)Methoxy]-3-hydroxypropyl Ester
L-VALINE,2-[(2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY]-3-HYDROXYPROPYLESTER,MONOHYDROCHLORIDE
L-VALINE, 2-[(2-AMINO-1,6-DIHYDRO-6-OXO-9H-PURIN-9-YL)METHOXY]-3-HYDROXYPROPYL ESTER, MONOHYDROCHLORIDE
L-Valine,2-[(2-aMino-1,6-dihydro-6-oxo-9H-purin-9-yl)Methoxy]-3-hydroxypropyl ester,hydrochloride (1:1)
L-Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester, monohydrochloride hydrate
2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate hydrochloride hydrate
[EINECS(EC#)]

641-360-4
[Molecular Formula]

C14H23ClN6O5
[MDL Number]

MFCD08460118
[MOL File]

175865-59-5.mol
[Molecular Weight]

390.82
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[Melting point ]

162-164°C
[storage temp. ]

Hygroscopic,-20°C Freezer, Under Inert Atmosphere
[solubility ]

H2O: ≥8mg/mL
[form ]

powder
[color ]

white to tan
[Stability:]

Hygroscopic
[InChI]

InChI=1/C14H22N6O5.ClH/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22;/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22);1H/t8?,9-;/s3
[InChIKey]

ZORWARFPXPVJLW-MTFPJWTKSA-N
[SMILES]

C12N(COC(CO)COC(=O)[C@H](C(C)C)N)C=NC=1C(=O)NC(N)=N2.Cl |&1:11,r|
[CAS DataBase Reference]

175865-59-5
Hazard InformationBack Directory
[Chemical Properties]

White Crystalline Solid
[Usage]

A pro-drug of ganciclovir. Used in treatment of retro-virus?
[Usage]

antibacterial, inhibits protein 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.
[Originator]

Roche (Switzerland)
[Uses]

Valganciclovir hydrochloride hydrate may be used in HIV-related cell signaling studies.
[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.
[Brand name]

Valcyte (Roche).
[General Description]

Valganciclovir Hydrochloride is the L-valyl ester of ganciclovir and an antiviral drug, widely used to treat cytomegalovirus infections.
Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards.
[Biochem/physiol Actions]

Valganciclovir hydrochloride hydrate is an antiviral used to treat cytomegalovirus infection. It is the prodrug of ganciclovir, a synthetic analog of 2′-deoxy-guanosine which is phosphorylated to a dGTP analog that competitively inhibits the incorporation of dGTP by viral DNA polymerase.
[Side effects]

Side effects of Valganciclovir hydrochloride include: leukopenia, neutropenia, anaemia, thrombocytopenia, pancytopenia, bone marrow failure and aplastic anaemia. Based on animal data and limited human data, Valganciclovir Oral Solution may temporarily or permanently inhibit spermatogenesis in males and inhibit fertility in females, which in turn may lead to birth defects in humans. It may also cause cancer in humans.
[storage]

Store at 2-8°C
Safety DataBack Directory
[WGK Germany ]

3
[HS Code ]

2933595960
Spectrum DetailBack Directory
[Spectrum Detail]

Valganciclovir hydrochloride(175865-59-5)1HNMR
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