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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB00577
rdf:type
n6:Drug
n6:description
Valaciclovir (INN) or valacyclovir (USAN) is an antiviral drug used in the management of herpes simplex and herpes zoster (shingles). It is a prodrug, being converted in vivo to aciclovir. It is marketed by GlaxoSmithKline under the trade name Valtrex or Zelitrex. [Wikipedia]
n6:dosage
n25:271B4D4D-363D-11E5-9242-09173F13E4C5 n25:271B4D4E-363D-11E5-9242-09173F13E4C5 n25:271B4D4F-363D-11E5-9242-09173F13E4C5 n25:271B4D4C-363D-11E5-9242-09173F13E4C5
n6:generalReferences
# O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/2653790 # Umapathy NS, Ganapathy V, Ganapathy ME: Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+). Pharm Res. 2004 Jul;21(7):1303-10. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15290873
n6:group
investigational approved
n6:halfLife
2.5-3.3 hours
n6:indication
For the treatment or suppression of cold sores (herpes labialis), herpes zoster (shingles), genital herpes in immunocompetent individuals, and recurrent genital herpes in HIV-infected individuals.
n6:manufacturer
n20:271B4D42-363D-11E5-9242-09173F13E4C5 n20:271B4D39-363D-11E5-9242-09173F13E4C5 n20:271B4D3A-363D-11E5-9242-09173F13E4C5 n20:271B4D3D-363D-11E5-9242-09173F13E4C5 n20:271B4D3E-363D-11E5-9242-09173F13E4C5 n20:271B4D3B-363D-11E5-9242-09173F13E4C5 n20:271B4D3C-363D-11E5-9242-09173F13E4C5 n20:271B4D41-363D-11E5-9242-09173F13E4C5 n20:271B4D43-363D-11E5-9242-09173F13E4C5 n20:271B4D3F-363D-11E5-9242-09173F13E4C5 n20:271B4D40-363D-11E5-9242-09173F13E4C5
owl:sameAs
n30:DB00577 n31:DB00577
dcterms:title
Valaciclovir
adms:identifier
n4:Valaciclovir n5:C07184 n8:54770 n9:DB00577 n11:PA451839 n12:60773 n13:D00398 n14:0173-0933-08 n15:50162073 n24:46508197
n6:mechanismOfAction
Valaciclovir is phosphorylated by viral thymidine kinase to acyclovir triphosphate (the active metabolite) which then inhibits herpes viral DNA replication by competitive inhibition of viral DNA polymerase, and by incorporation into and termination of the growing viral DNA chain. When used as a substrate for viral DNA polymerase, acyclovir triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where acyclovir triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand.
n6:packager
n20:271B4D19-363D-11E5-9242-09173F13E4C5 n20:271B4D1A-363D-11E5-9242-09173F13E4C5 n20:271B4D18-363D-11E5-9242-09173F13E4C5 n20:271B4D35-363D-11E5-9242-09173F13E4C5 n20:271B4D36-363D-11E5-9242-09173F13E4C5 n20:271B4D33-363D-11E5-9242-09173F13E4C5 n20:271B4D34-363D-11E5-9242-09173F13E4C5 n20:271B4D31-363D-11E5-9242-09173F13E4C5 n20:271B4D32-363D-11E5-9242-09173F13E4C5 n20:271B4D2F-363D-11E5-9242-09173F13E4C5 n20:271B4D1E-363D-11E5-9242-09173F13E4C5 n20:271B4D30-363D-11E5-9242-09173F13E4C5 n20:271B4D37-363D-11E5-9242-09173F13E4C5 n20:271B4D38-363D-11E5-9242-09173F13E4C5 n20:271B4D25-363D-11E5-9242-09173F13E4C5 n20:271B4D21-363D-11E5-9242-09173F13E4C5 n20:271B4D26-363D-11E5-9242-09173F13E4C5 n20:271B4D23-363D-11E5-9242-09173F13E4C5 n20:271B4D1F-363D-11E5-9242-09173F13E4C5 n20:271B4D24-363D-11E5-9242-09173F13E4C5 n20:271B4D20-363D-11E5-9242-09173F13E4C5 n20:271B4D1D-363D-11E5-9242-09173F13E4C5 n20:271B4D22-363D-11E5-9242-09173F13E4C5 n20:271B4D1B-363D-11E5-9242-09173F13E4C5 n20:271B4D1C-363D-11E5-9242-09173F13E4C5 n20:271B4D2D-363D-11E5-9242-09173F13E4C5 n20:271B4D2E-363D-11E5-9242-09173F13E4C5 n20:271B4D2B-363D-11E5-9242-09173F13E4C5 n20:271B4D2C-363D-11E5-9242-09173F13E4C5 n20:271B4D29-363D-11E5-9242-09173F13E4C5 n20:271B4D2A-363D-11E5-9242-09173F13E4C5 n20:271B4D27-363D-11E5-9242-09173F13E4C5 n20:271B4D28-363D-11E5-9242-09173F13E4C5
n6:patent
n27:5879706 n27:1340083 n27:2243237 n27:4957924
n6:routeOfElimination
Acyclovir accounted for 89% of the radioactivity excreted in the urine.
n6:synonym
L-Valine ester with 9-((2-hydroxyethoxy)methyl)guanine L-Valine, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester Valaciclovirum Valacyclovir
n6:toxicity
Adverse effects of overexposure might include headache and nausea.
n6:proteinBinding
13-18%
n6:salt
n6:synthesisReference
Marina Etinger, "Synthesis and purification of valacyclovir." U.S. Patent US20030153757, issued August 14, 2003.
n18:hasConcept
n19:M0224608
foaf:page
n22:val1474.shtml n23:valacyclovir.html n28:valacyclovir.htm
n6:IUPAC-Name
n7:271B4D54-363D-11E5-9242-09173F13E4C5
n6:InChI
n7:271B4D5A-363D-11E5-9242-09173F13E4C5
n6:Molecular-Formula
n7:271B4D59-363D-11E5-9242-09173F13E4C5
n6:Molecular-Weight
n7:271B4D56-363D-11E5-9242-09173F13E4C5
n6:Monoisotopic-Weight
n7:271B4D57-363D-11E5-9242-09173F13E4C5
n6:SMILES
n7:271B4D58-363D-11E5-9242-09173F13E4C5
n6:Water-Solubility
n7:271B4D52-363D-11E5-9242-09173F13E4C5
n6:logP
n7:271B4D50-363D-11E5-9242-09173F13E4C5 n7:271B4D53-363D-11E5-9242-09173F13E4C5 n7:271B4D6A-363D-11E5-9242-09173F13E4C5
n6:logS
n7:271B4D51-363D-11E5-9242-09173F13E4C5
n16:hasATCCode
n17:J05AB11
n6:H-Bond-Acceptor-Count
n7:271B4D60-363D-11E5-9242-09173F13E4C5
n6:H-Bond-Donor-Count
n7:271B4D61-363D-11E5-9242-09173F13E4C5
n6:InChIKey
n7:271B4D5B-363D-11E5-9242-09173F13E4C5
n6:Polar-Surface-Area--PSA-
n7:271B4D5C-363D-11E5-9242-09173F13E4C5
n6:Polarizability
n7:271B4D5E-363D-11E5-9242-09173F13E4C5
n6:Refractivity
n7:271B4D5D-363D-11E5-9242-09173F13E4C5
n6:Rotatable-Bond-Count
n7:271B4D5F-363D-11E5-9242-09173F13E4C5
n6:absorption
After oral administration, valaciclovir hydrochloride is rapidly absorbed from the gastrointestinal tract. The absolute bioavailability of acyclovir after administration of valaciclovir is 54.5% ± 9.1%.
n6:affectedOrganism
Human Herpes Virus
n6:casRegistryNumber
124832-26-4
n6:category
n6:clearance
* Renal cl=255 +/-  86 mL/min [healthy] * apparent cl=86.3 +/- 21.3 mL/min/1.73 m2 [dialysis patients] * apparent cl=679.16 +/- 162.76 mL/min/1.73 m2 [healthy]
n6:containedIn
n10:271B4D45-363D-11E5-9242-09173F13E4C5 n10:271B4D46-363D-11E5-9242-09173F13E4C5 n10:271B4D44-363D-11E5-9242-09173F13E4C5 n10:271B4D4B-363D-11E5-9242-09173F13E4C5 n10:271B4D49-363D-11E5-9242-09173F13E4C5 n10:271B4D4A-363D-11E5-9242-09173F13E4C5 n10:271B4D47-363D-11E5-9242-09173F13E4C5 n10:271B4D48-363D-11E5-9242-09173F13E4C5
n6:Bioavailability
n7:271B4D66-363D-11E5-9242-09173F13E4C5
n6:Ghose-Filter
n7:271B4D68-363D-11E5-9242-09173F13E4C5
n6:MDDR-Like-Rule
n7:271B4D69-363D-11E5-9242-09173F13E4C5
n6:Number-of-Rings
n7:271B4D65-363D-11E5-9242-09173F13E4C5
n6:Physiological-Charge
n7:271B4D64-363D-11E5-9242-09173F13E4C5
n6:Rule-of-Five
n7:271B4D67-363D-11E5-9242-09173F13E4C5
n6:Traditional-IUPAC-Name
n7:271B4D55-363D-11E5-9242-09173F13E4C5
n6:pKa--strongest-acidic-
n7:271B4D62-363D-11E5-9242-09173F13E4C5
n6:pKa--strongest-basic-
n7:271B4D63-363D-11E5-9242-09173F13E4C5