maribavir   Click here for help

GtoPdb Ligand ID: 12049

Synonyms: 1263W94 | benzimidavir | Camvia® | G1263 | GW-1263 | Livtencity®
Approved drug
maribavir is an approved drug (FDA (2021), EMA (2022))
Compound class: Synthetic organic
Comment: Maribavir is an orally bioavailable benzimidazole L-riboside that inhibits cytomegalovirus (CMV) pUL97 kinase with nM potency in vitro [1]. It inhibits viral replication.
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 6
Hydrogen bond donors 4
Rotatable bonds 4
Topological polar surface area 99.77
Molecular weight 375.08
XLogP 2.5
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 OC[C@@H]1O[C@@H]([C@H]([C@H]1O)O)n1c(NC(C)C)nc2c1cc(Cl)c(c2)Cl
Isomeric SMILES CC(C)Nc1nc2cc(c(cc2n1[C@@H]1[C@H]([C@H]([C@@H](O1)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
InChI Key KJFBVJALEQWJBS-XUXIUFHCSA-N
References
1. Biron KK, Harvey RJ, Chamberlain SC, Good SS, Smith 3rd AA, Davis MG, Talarico CL, Miller WH, Ferris R, Dornsife RE et al.. (2002)
Potent and selective inhibition of human cytomegalovirus replication by 1263W94, a benzimidazole L-riboside with a unique mode of action.
Antimicrob Agents Chemother, 46 (8): 2365-72. [PMID:12121906]
2. Kang C. (2022)
Maribavir: First Approval.
Drugs, 82 (3): 335-340. [PMID:35147913]
3. Marty FM, Ljungman P, Papanicolaou GA, Winston DJ, Chemaly RF, Strasfeld L, Young JA, Rodriguez T, Maertens J, Schmitt M et al.. (2011)
Maribavir prophylaxis for prevention of cytomegalovirus disease in recipients of allogeneic stem-cell transplants: a phase 3, double-blind, placebo-controlled, randomised trial.
Lancet Infect Dis, 11 (4): 284-92. [PMID:21414843]
4. Papanicolaou GA, Silveira FP, Langston AA, Pereira MR, Avery RK, Uknis M, Wijatyk A, Wu J, Boeckh M, Marty FM et al.. (2019)
Maribavir for Refractory or Resistant Cytomegalovirus Infections in Hematopoietic-cell or Solid-organ Transplant Recipients: A Randomized, Dose-ranging, Double-blind, Phase 2 Study.
Clin Infect Dis, 68 (8): 1255-1264. [PMID:30329038]