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
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]