Valacyclovir

ISO 17034:
Catalog Number : CS-O-02557
CAS Number : 124832-26-4
Status : Available for immediate dispatch
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Product Information

Product Name : Valacyclovir
Category : API Standards
Purity : >98%
Molecular Weight : 324.34 mol/g
Molecular Formula : C₁₃H₂₀N₆O₄
Application : The L-Valine ester prodrug of Acyclovir.
Therapeutic : Antiretroviral / Anti-HIV

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Status : Available for immediate dispatch
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Hazardous Compound : No

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References : "Beachamp; L,M,; et al,: Antiviralchem,chemother,; 3; 157 (1992); Weller; S,; et al,:clin, Pharmcol, Ther,; 54; 595 (1996); Lowace; D,; et al,: N, Engl, J, Med,; 340; 1462 (1999);"
Canonical SMILES : CC(C)C(C(=O)OCCOCN1C=NC2=C1N=C(NC2=O)N)N
Isomeric SMILES : CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N=C(NC2=O)N)N
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
InchIKey : HDOVUKNUBWVHOX-QMMMGPOBSA-N
IUPAC Name : 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
Exact Mass : 324.15460314
Melting Point : 170-172
Use Classification : Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Hazard Class : Acute Tox. 4 (100%)
Description : Valacyclovir is a L-valyl ester. It has a role as an antiviral drug. It derives from a guanine.
Disposal Methods : SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
EC Number : 603-015-6
Toxicity Summary : **LD50 Oral** Rat – 903.5 mg/kg **Carcinogenesis, Mutagenesis, Impairment of Fertility** Valacyclovir was noncarcinogenic in lifetime carcinogenicity assays at single daily gavage doses of valacyclovir giving plasma acyclovir concentrations equivalent to human levels in the mouse bioassay and 1.4 to 2.3 times human levels in the rat bioassay. No clinically significant difference in the incidence of tumors between treated and control animals was observed, and valacyclovir was not found to shorten the latency period of tumors. Valacyclovir was tested in 5 genetic toxicity assays. An Ames assay was negative in the absence or presence of metabolic activation. An in vitro cytogenetic study with human lymphocytes and a rat cytogenetic study was negative. In the mouse lymphoma assay, valacyclovir was not found to be mutagenic without metabolic activation, however, in the presence of metabolic activation (76% to 88% conversion to acyclovir), valacyclovir was mutagenic. Valacyclovir was also found to be mutagenic in a mouse micronucleus assay. Valacyclovir did not impair fertility or reproduction in rats at 6 times the normal concentrations in human plasma. **Use in pregnancy** Valacyclovir is categorized as a pregnancy category B drug. There are insufficient well-controlled studies of valacyclovir in pregnant women. The general rate of birth defects in infants exposed to acyclovir in-utero is comparable to the rate for infants measured in the general population. This drug should be used during pregnancy only if the potential benefit justifies the possible fetal risk. **Use in nursing** Acyclovir, a major metabolite of valacyclovir, was excreted in breastmilk at lower concentrations when a normal therapeutic dose of valacyclovir was administered. Exercise caution when acyclovir is used while nursing. **A note on renal function and toxicity in elderly patients** Elderly patients and patients with decreased renal function are at increased risk of valacyclovir toxicity, which can sometimes lead to central nervous system effects, such as encephalopathy, agitation, dysarthria, mania, and psychosis, among other effects. Consider reducing the dose of this drug in these populations to decrease the risk of toxicity.
Antidoteand Emergency Treatment : Emergency and supportive measures: Maintain an open airway and assist ventilation if needed. Treat coma, seizures, hypotension or anaphylaxis if they occur. Replace fluid losses resulting from gastroenteritis with intravenous crystalloids. Maintain steady urine flow with intravenous fluids to alleviate crystalluria and reverse renal dysfunction. Treat lactic acidosis with judicious doses of sodium bicarbonate and by withdrawal of the offending drug. /Antiviral and antiretroviral agents/
Human Toxicity Excerpts : /CASE REPORTS/ Drug-related eruptions that appear only on intertriginous or flexural folds and in gluteal areas have recently been termed symmetrical drug-related intertriginous and flexural exanthema (SDRIFE). We report a case of a 56-year-old woman with acute erythematous rash in the intertriginous areas after treatment with the L-valine ester of acyclovir, valacyclovir. Oral-challenge tests resulted in erythematous pruritic rash in the intertriginous area by valacyclovir. The patient was diagnosed as having SDRIFE due to valacyclovir.