U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H19Cl2N3O4
Molecular Weight 376.2355
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MARIBAVIR

SMILES

CC(C)N=c1[nH]c2cc(c(cc2n1[C@]3([H])[C@]([H])([C@]([H])([C@]([H])(CO)O3)O)O)Cl)Cl

InChI

InChIKey=KJFBVJALEQWJBS-XUXIUFHCSA-N
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

HIDE SMILES / InChI

Molecular Formula C15H19Cl2N3O4
Molecular Weight 376.2355
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Maribavir (previously known as 1263W94) is a novel benzimidazole riboside compound. This drug was in phase III of clinical trial for the prevention of cytomegalovirus (CMV) infections in transplant patients, sponsored by ViroPharma. However, drug failed to demonstrate a higher efficacy rate than the placebo. Maribavir has activity against cytomegalovirus and Epstein-Barr virus (EBV), but not against other human herpesviruses. Maribavir’s mechanism of action is unique and is complex compared to the currently approved antivirals for CMV. Maribavir inhibits the viral UL97 kinase rather than the viral DNA polymerase. The UL97 kinase is important for viral DNA elongation, DNA packaging, and nuclear egress of encapsidated viral DNA. In addition, maribavir inhibits the EBV DNA polymerase processivity factor (BMRF1), reduces the level of certain EBV glycoproteins, and inhibits viral transcription. However, future work will be designed to address the interaction of MBV and BGLF4 and to evaluate the mechanisms through which maribavir downregulates viral transcripts. BGLF4 belongs to the family of conserved herpesvirus PKs, which includes HCMV UL97, HSV UL13, and HSV US3. Maribavir does need to be phosphorylated for its activity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P16788|||Q91B49
Gene ID: NA
Gene Symbol: UL97
Target Organism: Human cytomegalovirus (strain AD169) (HHV-5) (Human herpesvirus 5)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Development of novel benzimidazole riboside compounds for treatment of cytomegalovirus disease.
1999
A novel nonnucleoside inhibitor specifically targets cytomegalovirus DNA maturation via the UL89 and UL56 gene products.
2001 Oct
Potent and selective inhibition of human cytomegalovirus replication by 1263W94, a benzimidazole L-riboside with a unique mode of action.
2002 Aug
Interactions of 1263W94 with other antiviral agents in inhibition of human cytomegalovirus replication.
2003 Apr
In vitro activities of benzimidazole D- and L-ribonucleosides against herpesviruses.
2003 Jul
Mechanism of action of the ribopyranoside benzimidazole GW275175X against human cytomegalovirus.
2004 May
Patents

Sample Use Guides

100 mg twice daily for up to 12 weeks
Route of Administration: Oral
Maribavir (MBV) may be linked to indirect effects on the transcription of Epstein-Barr virus (EBV) genes through the interaction of BGLF4 with multiple viral proteins. It was examined the effects of MBV and acyclovir (ACV) on the expression of the early (EA-D) and the late (gp125 and gp350) viral proteins by immunofluorescence staining. EA-D was detected in the nucleus, while both gp125 and gp350 were detected in the cytoplasm. MBV (20 μM) reduced the number of cells expressing EA-D by about 50% and almost eliminated the expression of gp125 and gp350 . It was revealed the potent inhibitory effect of MBV on the phosphorylation of EA-D during lytic infection and the lack of such an effect produced by ACV. Both drugs inhibited the expression of the two late viral glycoproteins, but MBV had a considerably greater effect, probably due to its greater antiviral potency.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:40:56 UTC 2021
Edited
by admin
on Sat Jun 26 09:40:56 UTC 2021
Record UNII
PTB4X93HE1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MARIBAVIR
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
MARIBAVIR [INN]
Common Name English
1263-W-94
Code English
MARIBAVIR [USAN]
Common Name English
5,6-DICHLORO-N-(1-METHYLETHYL)-1-.BETA.-L-RIBOFURANOSYL-1H-BENZIMIDAZOL-2-AMINE
Common Name English
5,6-DICHLORO-2-(ISOPROPYLAMINO)-1-.BETA.-L-RIBOFURANOSYLBENZIMIDAZOLE
Common Name English
1263W94
Code English
MARIBAVIR [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ05AX10
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
FDA ORPHAN DRUG 332210
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
NCI_THESAURUS C1556
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
FDA ORPHAN DRUG 229906
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
NCI_THESAURUS C281
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
WHO-ATC J05AX10
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
NCI_THESAURUS C1404
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
EU-Orphan Drug EU/3/07/519
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
Code System Code Type Description
MESH
C400401
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
EPA CompTox
176161-24-3
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
DRUG BANK
DB06234
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
PUBCHEM
471161
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
WIKIPEDIA
MARIBAVIR
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
FDA UNII
PTB4X93HE1
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
EVMPD
SUB03090MIG
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL515408
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
NCI_THESAURUS
C82254
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
CAS
176161-24-3
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
INN
7812
Created by admin on Sat Jun 26 09:40:56 UTC 2021 , Edited by admin on Sat Jun 26 09:40:56 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY