PMEG (antiviral)

PMEG

Names
Preferred IUPAC name {[2-(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)ethoxy]methyl}phosphonic acid
Other names 9-((2-Phosphonylmethoxy)ethyl)guanine
Identifiers
CAS Number	114088-58-3 Y
3D model (JSmol)	Interactive image
ChemSpider	58514
ECHA InfoCard	100.208.448
PubChem CID	64989
UNII	N9YOI96LPP Y
CompTox Dashboard (EPA)	DTXSID90150649
InChI InChI=1S/C8H12N5O5P/c9-8-11-6-5(7(14)12-8)10-3-13(6)1-2-18-4-19(15,16)17/h3H,1-2,4H2,(H2,15,16,17)(H3,9,11,12,14) Key: NZVORGQIEFTOQZ-UHFFFAOYSA-N
SMILES c1nc2c(n1CCOCP(=O)(O)O)[nH]c(nc2=O)N
Properties
Chemical formula	C8H12N5O5P
Molar mass	289.188 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

PMEG (9-[2-(phosphonomethoxy)ethyl] guanine) is an acyclic nucleoside phosphonate. Acyclic nucleoside phosphonates can have significant antiviral, cytostatic and antiproliferative activities.^[1] PMEG can inhibit cell proliferation and cause genotoxicity.^[2] PMEG is active against leukemia and melanoma in animal tumor models,^[3] and also has antiviral activities against herpes viruses in murine models.^[4][5]

Successful application of PMEG and PMEG-derivatives analogs may depend on the development analogs with reduced toxicity and enhanced pharmacokinetic properties to tissues. There are no clinical trials using PMEG listed at clinicaltrials.gov. This suggests that the pharmacokinetic properties of PMEG were too toxic to process forward with. There are several different PMEG-derivatives analogs currently being investigated. GS-9191 and GS-9219 prodrugs are just two of the next generation PMEG compounds being evaluated for antiviral and anticancer activities.^[6] Both GS-9191 and GS-9219 have made it into clinical trials, but require additional study.^{[citation needed]}