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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
InChI Key HDOVUKNUBWVHOX-QMMMGPOBSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1995, prior history not available))
IUPAC Name Click here for help
2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
International Nonproprietary Names Click here for help
INN number INN
7106 valaciclovir
Synonyms Click here for help
256U87 HCl | valacyclovir hydrochloride (monohydrate) | Valtrex® | Zelitrex®
Database Links Click here for help
CAS Registry No. 124832-26-4 (source: Scifinder)
ChEMBL Ligand CHEMBL1349
DrugBank Ligand DB00577
DrugCentral Ligand 2798
GtoPdb PubChem SID 178101526
PubChem CID 60773
RCSB PDB Ligand TXC
Search Google for chemical match using the InChIKey HDOVUKNUBWVHOX-QMMMGPOBSA-N
Search Google for chemicals with the same backbone HDOVUKNUBWVHOX
Search PubMed clinical trials valaciclovir
Search PubMed titles valaciclovir
Search PubMed titles/abstracts valaciclovir
Search UniChem for chemical match using the InChIKey HDOVUKNUBWVHOX-QMMMGPOBSA-N
Search UniChem for chemicals with the same backbone HDOVUKNUBWVHOX
Wikipedia Valacyclovir