Maribavir

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Maribavir
Accession Number
DB06234
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
1263-W-94 / 1263W94
International/Other Brands
Camvia (ViroPharma Inc.)
Categories
UNII
PTB4X93HE1
CAS number
176161-24-3
Weight
Average: 376.23
Monoisotopic: 375.0752615
Chemical Formula
C15H19Cl2N3O4
InChI Key
KJFBVJALEQWJBS-XUXIUFHCSA-N
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
IUPAC Name
(2S,3S,4R,5S)-2-{5,6-dichloro-2-[(propan-2-yl)amino]-1H-1,3-benzodiazol-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
SMILES
CC(C)NC1=NC2=CC(Cl)=C(Cl)C=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O

Pharmacology

Indication

Investigated for use/treatment in viral infection, transplantation (organ or tissue), cytomegalovirus (CMV) retinitis, and retinal disorders (unspecified).

Pharmacodynamics
Not Available
Mechanism of action

Maribavir is part of a new class of anti-cytomegalovirus (CMV) , benzimidazole ribosides, that inhibit viral DNA assembly and inhibits egress of viral capsids from the nucleus of infected cells. Maribavir is active in vitro against strains of CMV that are resistant to commonly used anti-CMV drugs. [ViroPharma] Maribavir inhibits the human CMV UL97 viral protein kinase which prevents the virus from encapsulating and leaving infected cells.

TargetActionsOrganism
USerine/threonine protein kinase UL97Not AvailableHHV-5
USerine/threonine protein kinase UL97Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Maribavir.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Maribavir.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Maribavir.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Maribavir.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Maribavir.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Maribavir.
Human adenovirus e serotype 4 strain cl-68578 antigenThe therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Maribavir.
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Maribavir.
Typhoid Vaccine LiveThe therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Maribavir.
Vibrio cholerae CVD 103-HgR strain live antigenThe therapeutic efficacy of Vibrio cholerae CVD 103-HgR strain live antigen can be decreased when used in combination with Maribavir.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Steininger C: Novel therapies for cytomegalovirus disease. Recent Pat Antiinfect Drug Discov. 2007 Jan;2(1):53-72. [PubMed:18221163]
  2. Winston DJ, Young JA, Pullarkat V, Papanicolaou GA, Vij R, Vance E, Alangaden GJ, Chemaly RF, Petersen F, Chao N, Klein J, Sprague K, Villano SA, Boeckh M: Maribavir prophylaxis for prevention of cytomegalovirus infection in allogeneic stem cell transplant recipients: a multicenter, randomized, double-blind, placebo-controlled, dose-ranging study. Blood. 2008 Jun 1;111(11):5403-10. doi: 10.1182/blood-2007-11-121558. Epub 2008 Feb 19. [PubMed:18285548]
  3. Link [Link]
External Links
ChemSpider
413807
ChEMBL
CHEMBL515408
Wikipedia
Maribavir
ATC Codes
J05AX10 — Maribavir

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceCytomegalovirus (CMV)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infections, Cytomegalovirus1
2CompletedPreventionInfections, Cytomegalovirus1
2CompletedTreatmentCytomegalovirus (CMV) / Infections, Cytomegalovirus1
3CompletedPreventionInfections, Cytomegalovirus2
3RecruitingTreatmentCytomegalovirus (CMV)2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.72 mg/mLALOGPS
logP2.15ALOGPS
logP1.84ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)6.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.77 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.01 m3·mol-1ChemAxon
Polarizability37.49 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzimidazole ribonucleosides and ribonucleotides. These are nucleosides with a structure that consists of an imidazole moiety of benzimidazole is N-linked to a ribose (or deoxyribose). Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Benzimidazole ribonucleosides and ribonucleotides
Sub Class
Not Available
Direct Parent
Benzimidazole ribonucleosides and ribonucleotides
Alternative Parents
Glycosylamines / Pentoses / Benzimidazoles / Secondary alkylarylamines / N-substituted imidazoles / Aminoimidazoles / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Tetrahydrofurans
show 7 more
Substituents
1-ribofuranosylbenzimidazole / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Benzimidazole / Secondary aliphatic/aromatic amine / Aminoimidazole / Aryl chloride / Aryl halide / Monosaccharide
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
HHV-5
Pharmacological action
Unknown
General Function
Protein kinase activity
Specific Function
Serine/threonine protein kinase that plays important roles in several processes including nuclear viral egress, viral replication or regulation of host cell cycle progression. Participates in the a...
Gene Name
UL97
Uniprot ID
P16788
Uniprot Name
Serine/threonine protein kinase UL97
Molecular Weight
78231.9 Da
Kind
Protein
Organism
Not Available
Pharmacological action
Unknown
General Function
Protein kinase activity
Specific Function
Serine/threonine protein kinase that plays important roles in several processes including nuclear viral egress, viral replication or regulation of host cell cycle progression. Participates in the a...
Gene Name
UL97
Uniprot ID
Q68101
Uniprot Name
Serine/threonine protein kinase UL97
Molecular Weight
78246.87 Da

Drug created on March 19, 2008 10:18 / Updated on September 02, 2019 18:18