valacyclovir   Click here for help

GtoPdb Ligand ID: 4824

Synonyms: 256U87 HCl | valacyclovir hydrochloride (monohydrate) | Valtrex® | Zelitrex®
Approved drug PDB Ligand
valacyclovir is an approved drug (FDA (1995, prior history not available))
Compound class: Synthetic organic
Comment: Valacyclovir s an esterified prodrug, which is converted to aciclovir in vivo. Esterification increases the oral bioavailability of the prodrug compared to the parent molecule.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 151.14
Molecular weight 324.15
XLogP 1.28
No. Lipinski's rules broken 0
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Canonical SMILES CC(C(C(=O)OCCOCn1cnc2c1[nH]c(N)nc2=O)N)C
Isomeric SMILES CC([C@@H](C(=O)OCCOCn1cnc2c1[nH]c(N)nc2=O)N)C
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
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Summary of Clinical Use Click here for help
Used in the treatment and suppression of cold sores, herpes zoster (shingles), and genital herpes.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The phosphorylation products of valacyclovir inhibit herpes viral DNA replication by competitive inhibition of viral DNA polymerase.
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