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SML0191

Sigma-Aldrich

Valganciclovir hydrochloride hydrate

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C14H22N6O5·HCl · xH2O
CAS Number:
175865-59-5
Molecular Weight:
390.82 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329825218
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

H2O: ≥8 mg/mL

originator

Roche

storage temp.

−20°C

SMILES string

O.Cl.CC(C)[C@H](N)C(=O)OCC(CO)OCn1cnc2C(=O)N=C(N)Nc12

InChI

1S/C14H22N6O5.ClH.H2O/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;1H2/t8?,9-;;/m0../s1

InChI key

XASVRRIYQZVANH-AHBBCRTASA-N

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Application

Valganciclovir hydrochloride hydrate may be used in HIV-related cell signaling studies.

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.
Valganciclovir is a valine ester of Ganciclovir, used to treat cytomegalovirus retinitis in HIV-infected patients. It is rapidly metabolized to ganciclovir by hydrolysis before entering the systemic circulation resulting in improved absorption of the drug.

Features and Benefits

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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M Curran et al.
Drugs, 61(8), 1145-150 (2001-07-24)
Valganciclovir is a prodrug of ganciclovir which has been developed for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS. Oral valganciclovir is rapidly absorbed and hydrolysed to ganciclovir. The oral bioavailability of ganciclovir after oral valganciclovir administration is
M D Pescovitz et al.
Antimicrobial agents and chemotherapy, 44(10), 2811-2815 (2000-09-19)
The pharmacokinetics of an orally administered valine ester of ganciclovir (GCV), valganciclovir (VGC), were studied. These were compared to the pharmacokinetics of oral and intravenous GCV. Twenty-eight liver transplant recipients received, in an open-label random order with a 3- to
Rachel E Bennett et al.
Journal of neurotrauma, 31(19), 1647-1663 (2014-05-07)
The pathological processes that lead to long-term consequences of multiple concussions are unclear. Primary mechanical damage to axons during concussion is likely to contribute to dysfunction. Secondary damage has been hypothesized to be induced or exacerbated by inflammation. The main

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