Valaciclovir

Prodrug of aciclovir for herpes virus treatment CAS# 124832-26-4

Valaciclovir

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Chemical structure

Valaciclovir

3D structure

Chemical Properties of Valaciclovir

Cas No. 124832-26-4 SDF Download SDF
PubChem ID 60773 Appearance Powder
Formula C13H20N6O4 M.Wt 324.34
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Valaciclovir
Solubility 25℃: DMSO
Chemical Name 2-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
SMILES CC(C)C(C(=O)OCCOCN1C=NC2=C1NC(=NC2=O)N)N
Standard InChIKey HDOVUKNUBWVHOX-QMMMGPOBSA-N
Standard InChI InChI=1S/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Valaciclovir

DescriptionValacyclovir is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B. IC50 Value: 2.9 microg/ml (for HSV-1 W)[4]. Target: HSV infection in vitro: 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 [5]. in vivo: 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[1]. 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 [2]. 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 [3]. Clinical trial: Evaluation of Valaciclovir in Patients with Chickenpox. Phage3

References:
[1]. Valacyclovir. New indication: for genital herpes, simpler administration. Can Fam Physician. 1999 Jul;45:1698-700, 1703-5. [2]. Lycke J, Malmestr?m C, St?hle L. 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.

Valaciclovir Dilution Calculator

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Valaciclovir Molarity Calculator

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Preparing Stock Solutions of Valaciclovir

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0832 mL 15.4159 mL 30.8318 mL 61.6637 mL 77.0796 mL
5 mM 0.6166 mL 3.0832 mL 6.1664 mL 12.3327 mL 15.4159 mL
10 mM 0.3083 mL 1.5416 mL 3.0832 mL 6.1664 mL 7.708 mL
50 mM 0.0617 mL 0.3083 mL 0.6166 mL 1.2333 mL 1.5416 mL
100 mM 0.0308 mL 0.1542 mL 0.3083 mL 0.6166 mL 0.7708 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Valaciclovir

IC50 Value: 2.9 microg/ml (for HSV-1 W)[4]. Valacyclovir, the metabolic precursor of , is now approved for treatment and prevention of genital infection with herpes simplex viruses [1]. in vitro: 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 [5]. in vivo: 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[1]. 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 [2]. 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 [3]. Clinical trial: Evaluation of Valaciclovir in Patients with Chickenpox. Phage3

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References on Valaciclovir

Prophylactic Efficacy Against Herpes Zoster and Costs Difference Between Acyclovir and Valaciclovir in Hematological Patients.[Pubmed:27566094]

In Vivo. 2016 09-10;30(5):701-5.

BACKGROUND: Immunocompromised hematological patients are at increased risk of herpes zoster (HZ). We examined the efficacy of acyclovir and Valaciclovir in preventing HZ. We also created a simulation to reduce prophylactic medicine costs. PATIENTS AND METHODS: We retrospectively evaluated 573 hematological patients who received chemotherapy, and assessed the difference in the costs between the acyclovir (Zovirax(R)) and Valaciclovir (Valtrex(R)) groups. RESULTS: Forty-four out of the 573 patients (7.7%) developed HZ. Out of them, there were 37 patients (84.1%) who received corticosteroids. Moreover, in total, there were 67 patients receiving acyclovir prophylaxis and 42 patients receiving Valaciclovir prophylaxis, out of which one from each group occurred with HZ. The total 5-year cost of acyclovir and Valaciclovir was yen2,869,917 and yen4,809,952, respectively. Therefore, by changing from Valaciclovir to acyclovir, medical costs could be reduced by 28.3%. Additionally, switching to generic inexpensive acyclovir would possibly reduce them to 15.0%. CONCLUSION: Chemotherapy, including corticosteroids, is associated with a high incidence of HZ. Additionally, there was no prophylactic difference between acyclovir and Valaciclovir. We expect that use of generic acyclovir could reduce prophylaxis costs by 85.0%.

Efficacy of interferon in recurrent valaciclovir-refractory erythema multiforme in a patient not infected with hepatitis C virus.[Pubmed:27334053]

Clin Exp Dermatol. 2016 Aug;41(6):648-50.

Recurrent erythema multiforme (EM) is rare and is most typically related to infections with herpes simplex virus. Prophylactic administration of Valaciclovir is the first-line treatment, but there is no agreement about second-line treatment in cases of ineffectiveness. We present a 31-year-old man who was not infected with hepatitis C virus (HCV), and had a history of severe and recurrent EM, unresponsive to Valaciclovir, colchicine and hydroxychloroquine. The patient noticed that an intermittent flu-like illness seemed to have abrogated an EM flare. Because of this observation, the next EM flares were treated with short courses of interferon, which gave rapid and complete efficacy. Efficacy of interferon in EM has only been reported in two previous patients, in whom the drug was administered to treat HCV infection. Efficiency was attributed to treatment of the underlying HCV infection, which was thought to be the origin of EM in both cases. This is the first case, to our knowledge, reporting a dramatic response to interferon-alfa in a patient who was not infected with HCV.

Valaciclovir to prevent Cytomegalovirus mediated adverse modulation of the immune system in ANCA-associated vasculitis (CANVAS): study protocol for a randomised controlled trial.[Pubmed:27450392]

Trials. 2016 Jul 22;17(1):338.

BACKGROUND: The ANCA-associated vasculitides (AAV) are systemic autoimmune inflammatory disorders characterised by necrotising inflammation affecting small to medium-sized blood vessels. Despite improvements in survival, infection and cardiovascular disease remain leading causes of morbidity and mortality. Considerable evidence suggests that CD4 + CD28null T-cell expansions, predominantly seen in Cytomegalovirus (CMV) seropositive individuals, are associated with systemic dysregulation of immune function leading to a heightened risk of infection and cardiovascular disease. In patients with AAV, CD4 + CD28null expansions are driven by CMV and are associated with an increased risk of infection and mortality. The aim of this study is to explore in detail the ways in which CMV modulates the immune system and to determine whether treatment with Valaciclovir blocks subclinical CMV reactivation in CMV seropositive AAV patients and ameliorates the CMV-induced adverse effects on the immune system. METHODS/DESIGN: CANVAS is a single-centre prospective open-label randomised controlled proof-of-concept trial of 50 adult CMV seropositive patients with stable AAV. Participants will be randomly allocated to receive Valaciclovir orally (2 g QDS or reduced according to renal function) or no additional treatment for 6 months with an additional 6-month follow-up period. The primary outcome is the proportion of patients with CMV reactivation, as assessed by measurable viral load on quantitative blood and urine CMV polymerase chain reaction. The secondary outcomes are safety, change in the proportion of CD4+ CMV-specific T-cell population (defined as CD4 + CD28null cells) and change in soluble markers of inflammation from baseline to 6 months. Further tertiary and exploratory outcomes include persistence of the effect of Valaciclovir on the proportion of CD4 + CD28null cells at 6 months post completion of treatment, change in the immune phenotype of CD4+ T cells and change in blood pressure and arterial stiffness parameters from baseline to 6 months. DISCUSSION: The results of this study will enable larger studies to be conducted to determine whether by controlling subclinical CMV reactivation, we can improve clinical endpoints such as infection and cardiovascular disease. The potential impact of this study is not limited to AAV, as CD4 + CD28null cells have been linked to adverse outcomes in other inflammatory conditions and in the context of an ageing immune system. TRIAL REGISTRATION: ClinicalTrials.gov Identifier NCT01633476 (registered 29 June 2012).

Description

Valacyclovir is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B.

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