Maribavir

Category	Cytomegalovirus (CMV)
CAS	176161-24-3
Description	1263W94 inhibited viral replication in a dose-dependent manner, with a mean 50% inhibitory concentration (IC50) of 0.12 ± 0.01 μM compared to a mean IC50 for GCV of 0.53 ± 0.04 μM, as measured by a multicycle DNA hybridization assay. Maribavir inhibits viral genome copy numbers and infectivity to levels similar to and exceeding levels produced by BGLF4 knockout virus. Introduction of 1.0 or 10 nM maribavir, a known pUL97 inhibitor, and subsequent Lineweaver-Burk analysis demonstrated competitive inhibition of CPV phosphorylation, with a Ki of 3.0+/-0.3 nM. Maribavir has significant activity against both human cytomegalovirus (CMV) and Epstein-Barr virus, but not other herpesviruses. Unlike ganciclovir, which needs to be phosphorylated by UL 97 kinase to become an active inhibitor of DNA polymerase, maribavir directly inhibits UL 97 kinase.

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Product Information

Synonyms	Maribavir; 1263W-94; BW-1263W-94; GW-1263; GW-257406X; SHP-620; VP-41263; BW-1263W94; 1263W94; BW1263W-94; GW1263; GW257406X; SHP620; VP41263; BW1263W94
IUPAC Name	(2S,3S,4R,5S)-2-[5,6-dichloro-2-(propan-2-ylamino)benzimidazol-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol
Molecular Weight	376.24
Molecular Formula	C15H19Cl2N3O4
Canonical SMILES	CC(C)NC1=NC2=CC(=C(C=C2N1C3C(C(C(O3)CO)O)O)Cl)Cl
InChI	InChI=1S/C15H19Cl2N3O4/c1-6(2)18-15-19-9-3-7(16)8(17)4-10(9)20(15)14-13(23)12(22)11(5-21)24-14/h3-4,6,11-14,21-23H,5H2,1-2H3,(H,18,19)/t11-,12-,13-,14-/m0/s1
InChIKey	KJFBVJALEQWJBS-XUXIUFHCSA-N
Boiling Point	611.0±65.0 °C at 760 mmHg
Flash Point	323.3±34.3 °C
Purity	>98%
Density	1.7±0.1 g/cm3
Solubility	In vitro: 10 mM in DMSO
Appearance	White to off-white (Solid)
Application	Antiviral Agents
Storage	Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month
Assay	For these studies MRC-5 cells are seeded in 24-well plates at ~5×104 cells/well and grown for 3 days in MEM 8-1-1 to confluence (~1.1×105 cells/well). The cells are infected with AD169 in MEM 2-1-1 at an MOI ranging from 1 to 3 and incubated at 37°C for 90 min to allow viral adsorption. The unadsorbed virus is removed and replaced with 1 mL of MEM 2-1-1. To test the effect of compounds on viral DNA synthesis or maturation, Maribavir, BDCRB, or GCV is added to the medium at the concentrations indicated for each experiment.
Complexity	447
Exact Mass	375.0752615
Index Of Refraction	1.703
In Vitro	Maribavir is a potent inhibitor of the autophosporylation of the wild type and all the major Ganciclovir (GCV) resistant UL97 mutants analysed with a mean IC50 of 35 nM. The M460I mutation results in hypersensitivity to Maribavir with an IC50 of 4.8 nM. A Maribavir resistant mutant of UL97 (L397R) is functionally compromised as both a Ganciclovir kinase and a protein kinase (~ 10% of wild type levels). Enzyme kinetic experiments demonstrate that Maribavir is a competitive inhibitor of ATP with a Ki of 10 nM. Maribavir (1263W94) inhibits viral replication in a dose-dependent manner, with IC50 of 0.12±0.01 μM as measured by a multicycle DNA hybridization assay. The pUL97 protein kinase is strongly inhibited by Maribavir, with 50% inhibition occurring at 3 nM.
PSA	99.77000
Target	CMV
Vapor Pressure	0.0±1.8 mmHg at 25°C
XLogP3-AA	2.2