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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key HDOVUKNUBWVHOX-QMMMGPOBSA-N
References
1. Balimane P, Sinko P. (2000)
Effect of ionization on the variable uptake of valacyclovir via the human intestinal peptide transporter (hPepT1) in CHO cells.
Biopharm Drug Dispos, 21 (5): 165-74. [PMID:11180195]
2. Balimane PV, Tamai I, Guo A, Nakanishi T, Kitada H, Leibach FH, Tsuji A, Sinko PJ. (1998)
Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir.
Biochem Biophys Res Commun, 250 (2): 246-51. [PMID:9753615]
3. Bhardwaj RK, Herrera-Ruiz D, Eltoukhy N, Saad M, Knipp GT. (2006)
The functional evaluation of human peptide/histidine transporter 1 (hPHT1) in transiently transfected COS-7 cells.
Eur J Pharm Sci, 27 (5): 533-42. [PMID:16289537]
4. Ganapathy ME, Huang W, Wang H, Ganapathy V, Leibach FH. (1998)
Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2.
Biochem Biophys Res Commun, 246 (2): 470-5. [PMID:9610386]
5. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ. (1999)
Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line.
J Pharmacol Exp Ther, 289 (1): 448-54. [PMID:10087037]
6. Minhas GS, Newstead S. (2019)
Structural basis for prodrug recognition by the SLC15 family of proton-coupled peptide transporters.
Proc Natl Acad Sci U S A, 116 (3): 804-809. [PMID:30602453]
7. Wang Y, Li P, Song F, Yang X, Weng Y, Ma Z, Wang L, Jiang H. (2019)
Substrate Transport Properties of the Human Peptide/Histidine Transporter PHT2 in Transfected MDCK Cells.
J Pharm Sci, 108 (10): 3416-3424. [PMID:31254495]