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Valganciclovir Hydrochloride

Names

[ CAS No. ]:
175865-59-5

[ Name ]:
Valganciclovir Hydrochloride

[Synonym ]:
(2S)-2-amino-3-méthylbutanoate de 2-[(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)méthoxy]-3-hydroxypropyle chlorhydrate
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-3,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester, monohydrochloride
2-[(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)methoxy]-3-hydroxypropyl L-valinate hydrochloride
2-[(2-Amino-6-oxo-3,6-dihydro-9H-purin-9-yl)methoxy]-3-hydroxypropyl-(2S)-2-amino-3-methylbutanoathydrochlorid
Valganciclovir Hydrochloride
Valganciclovir HCl
2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]-3-hydroxypropyl L-valinate hydrochloride (1:1)
L-Valine, 2-[(2-amino-3,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester, hydrochloride (1:1)
2-[(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate hydrochloride
L-Valine (2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]-3-hydroxypropyl ester
Valganciclovir (hydrochloride)

Biological Activity

[Description]:

Valganciclovir (hydrochloride), the L-valyl ester of ganciclovir, is actually a prodrug for ganciclovir. Valganciclovir is an antiviral medication used to treat cytomegalovirus infections.IC50 Value: Target: CMVin vitro: In cell culture model systems using Caco-2 cells for PEPT1 and SKPT cells for PEPT2, valganciclovir inhibited glycylsarcosine transport mediated by PEPT1 and PEPT2 with K(i) values (inhibition constant) of 1.68+/-0.30 and 0.043+/- 0.005 mM, respectively. The inhibition by valganciclovir was competitive in both cases [1].in vivo: 37 patients were enrolled; 19 patients received treatment with VGV and 18 patients received treatment with GCV. The VGV was not inferior in efficacy to GCV as pre-emptive therapy, with rates of viral clearance at 28 days of 89.5% and 83%, respectively (P-value for non-inferiority = 0.030). Toxicities were similar between the 2 arms. No patients developed CMV disease [2]. Patients being treated with an alemtuzumab-containing regimen received prophylaxis with either valaciclovir 500 mg orally daily orvalganciclovir 450 mg orally twice daily. None of the 20 patients randomized to valganciclovir experienced CMV reactivation (P = .004) [3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> CMV
Research Areas >> Infection

[References]

[1]. Sugawara M, et al. Transport of valganciclovir, a ganciclovir prodrug, via peptide transporters PEPT1 and PEPT2. J Pharm Sci. 2000 Jun;89(6):781-9.

[2]. Chawla JS, et al. Oral valganciclovir versus ganciclovir as delayed pre-emptive therapy for patients after allogeneic hematopoietic stem cell transplant: a pilot trial (04-0274) and review of the literature. Transpl Infect Dis. 2012 Jun;14(3):259-67.

[3]. O'Brien S, et al. Valganciclovir prevents cytomegalovirus reactivation in patients receiving alemtuzumab-based therapy. Blood. 2008 Feb 15;111(4):1816-9.


[Related Small Molecules]

Letermovir | Maribavir | Brivudine | B220 | Tomeglovir

Chemical & Physical Properties

[ Boiling Point ]:
629.1ºC at 760 mmHg

[ Molecular Formula ]:
C14H23ClN6O5

[ Molecular Weight ]:
390.823

[ Exact Mass ]:
390.141846

[ PSA ]:
171.37000

[ LogP ]:
0.64680

[ Vapour Pressure ]:
1.08E-16mmHg at 25°C

[ Storage condition ]:
-20°C

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds