valganciclovir   Click here for help

GtoPdb Ligand ID: 4716

Synonyms: Ro-1079070/194 | RS-079070-194 | Valcyte®
Approved drug
valganciclovir is an approved drug (FDA (2002, prior history not available))
Compound class: Synthetic organic
Comment: Valcyte® contains valganciclovir hydrochloride (PubChem CID 110632). This is a prodrug of ganciclovir (PubChem CID 3454). The INN document for this drug specifies that there is a chiral centre at (position t8) and the INN-assigned compound consists of two epimers depending on the stereochemistry at this position. The structure shown here does not specify stereochemistry at this point and represents the mixture. This is represented by the '?' in the InChI standard identifier on the 'Structure' tab.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: valganciclovir

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 4
Rotatable bonds 9
Topological polar surface area 171.37
Molecular weight 354.17
XLogP 0.61
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OCC(OCn1cnc2c1[nH]c(N)nc2=O)COC(=O)C(C(C)C)N
Isomeric SMILES OCC(OCn1cnc2c1[nH]c(N)nc2=O)COC(=O)[C@H](C(C)C)N
InChI InChI=1S/C14H22N6O5/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22)/t8?,9-/m0/s1
1. Sugawara M, Huang W, Fei YJ, Leibach FH, Ganapathy V, Ganapathy ME. (2000)
Transport of valganciclovir, a ganciclovir prodrug, via peptide transporters PEPT1 and PEPT2.
J Pharm Sci, 89 (6): 781-9. [PMID:10824137]
2. Umapathy NS, Ganapathy V, Ganapathy ME. (2004)
Transport of amino acid esters and the amino-acid-based prodrug valganciclovir by the amino acid transporter ATB(0,+).
Pharm Res, 21 (7): 1303-10. [PMID:15290873]
3. Ural-Blimke Y, Flayhan A, Strauss J, Rantos V, Bartels K, Nielsen R, Pardon E, Steyaert J, Kosinski J, Quistgaard EM et al.. (2019)
Structure of Prototypic Peptide Transporter DtpA from E. coli in Complex with Valganciclovir Provides Insights into Drug Binding of Human PepT1.
J Am Chem Soc, 141 (6): 2404-2412. [PMID:30644743]