Valacyclovir hydrochloride

Names

[ Name ]:
Valacyclovir hydrochloride

[Synonym ]:
2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester monohydrochloride
MFCD01861507
2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate hydrochloride
L-Valine 2-(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-ylmethoxy)ethyl Ester Hydrochloride Hydrate
Valaciclovir
2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl valinate hydrochloride (1:1)
2-[(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl-(2S)-2-amino-3-methylbutanoathydrochlorid
2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate hydrochloride
Valacyclovir hydrochloride
Zelitrex
Valaciclovir hydrochloride
(2S)-2-amino-3-méthylbutanoate de 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)méthoxy]éthyle chlorhydrate
Valaciclovir HCl
256u
L-Valine 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester monohydrochloride
Valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, hydrochloride (1:1)
Valacyclovir hydrochloride hydrate
Valacyclovir (hydrochloride)

Biological Activity

[Description]:

Valacyclovir hydrochloride is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B. Target: HSVValacyclovir is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B. VACV uptake was concentration dependent and saturable with a Michaelis-Menten constant and maximum velocity of 1.64 +/- 0.06 mM and 23.34 +/- 0.36 nmol/mg protein/5 min, respectively. A very similar Km value was obtained in hPEPT1/CHO cells and in rat and rabbit tissues and Caco-2 cells, suggesting that hPEPT1 dominates the intestinal transport properties of VACV in vitro . For treatment of a first episode of genital herpes, a large comparative trial has shown that valacyclovir (1 g twice a day) is as effective as acyclovir (200 mg five times a day) when given for 10 days. For treating recurrences, two trials show that valacyclovir is as effective as acyclovir (200 mg five times a day) with a treatment period of 5 days. A daily dose of 1 g of valacyclovir is as effective as 2 g daily. Valacyclovir can be administered once a day. The concentrations of acyclovir in serum and CSF were measured at steady state after 6 days of oral treatment with 1,000 mg of valacyclovir three times a day. EC50 values of PE and AC in 3T3 cells were 0.02 and 0.01 ug/ml, while values in BHK cells were 0.2 and 0.03 ug/ml. Treatment of infected immunosuppressed mice and FA and VA (b.i.d., 5.5 days) reduced the proportion with erythema from 100% to 24% and 38%, and eliminated ear paralysis, ear lesions (vesicles, etc) and death. Virus was absent from ear and brainstem by day 6, but reappeared after discontinuation in mice treated with VA.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HSV

Research Areas >> Infection

[References]

[1]. Valacyclovir. New indication: for genital herpes, simpler administration. Can Fam Physician. 1999 Jul;45:1698-700, 1703-5.

[2]. Lycke J, et al. Acyclovir levels in serum and cerebrospinal fluid after oral administration of valacyclovir. Antimicrob Agents Chemother. 2003 Aug;47(8):2438-41.

[3]. Comparison of efficacies of famciclovir and valaciclovir against herpes simplex virus type 1 in a murineimmunosuppression model. Antimicrob Agents Chemother. 1995 May;39(5):1114-9.

[4]. Dhaliwal DK, Romanowski EG, Yates KA, Valacyclovir inhibits recovery of ocular HSV-1 after experimental reactivation by excimer laser keratectomy. Cornea. 1999 Nov;18(6):693-9.

[5]. Guo A, Hu P, Balimane PV, Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line.J Pharmacol Exp Ther. 1999 Apr;289(1):448-54.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.55g/cm3

[ Boiling Point ]:
588.4ºC at 760 mmHg

[ Melting Point ]:
170-172ºC

[ Molecular Formula ]:
C₁₃H₂₁ClN₆O₄

[ Molecular Weight ]:
360.797

[ Flash Point ]:
309.7ºC

[ Exact Mass ]:
360.131287

[ PSA ]:
151.14000

[ LogP ]:
1.28590

[ Vapour Pressure ]:
7.95E-14mmHg at 25°C

[ Index of Refraction ]:
1.673

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Oral antiviral therapy for prevention of genital herpes outbreaks in immunocompetent and nonpregnant patients.

Cochrane Database Syst. Rev. 8 , CD009036, (2014)

Genital herpes is caused by herpes simplex virus 1 (HSV-1) or 2 (HSV-2). Some infected people experience outbreaks of genital herpes, typically, characterized by vesicular and erosive localized painfu...

Acute retinal necrosis associated with Epstein-Barr virus: immunohistopathologic confirmation.

JAMA Ophthalmol. 132(7) , 881-2, (2014)

Acute retinal necrosis (ARN) is an infectious retinitis primarily caused by the herpesviruses. Although the Epstein-Barr virus (EBV) has been implicated as a cause of ARN, to our knowledge, there has ...

A pilot study examining the safety and tolerability of valacyclovir in veterans with hepatitis C virus/herpes simplex virus type 2 coinfection.

Am. J. Med. Sci. 348(6) , 455-9, (2014)

We performed a pilot study examining the safety and tolerability of valacyclovir in veterans with herpes simplex virus type 2 and hepatitis C virus (HCV) coinfection.We performed a randomized double-b...