Maribavir

Base Information

• Chemical Name: Maribavir
• CAS No.: 176161-24-3
• Molecular Formula: C₁₅H₁₉Cl₂N₃O₄
• Molecular Weight: 376.24
• UNII: PTB4X93HE1
• DSSTox Substance ID: DTXSID60170091
• Nikkaji Number: J1.159.817J
• Wikipedia: Maribavir
• Wikidata: Q6762512
• NCI Thesaurus Code: C82254
• RXCUI: 2586068
• Metabolomics Workbench ID: 144506
• ChEMBL ID: CHEMBL515408
• Mol file: 176161-24-3.mol

Synonyms:1263-W-94;1263W94;5,6-dichloro-2-(isopropylamino)-1-beta-L-ribofuranosylbenzimidazole;benzimidavir;BW 1263W94;BW-1263W94;GW 1263;GW 257406X;GW-1263;GW-257406X;GW257406X;maribavir

Chemical Property of Maribavir

Chemical Property:

• Vapor Pressure: 8.74E-16mmHg at 25°C
• Boiling Point: 611°Cat760mmHg
• PKA: 13.20±0.70(Predicted)
• Flash Point: 323.3°C
• PSA: 99.77000
• Density: 1.67g/cm³
• LogP: 1.84790
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 375.0752615
• Heavy Atom Count: 24
• Complexity: 447

Purity/Quality:

99% ^*data from raw suppliers

Maribavir >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC(C)NC1=NC2=CC(=C(C=C2N1C3C(C(C(O3)CO)O)O)Cl)Cl
• Isomeric SMILES: CC(C)NC1=NC2=CC(=C(C=C2N1[C@@H]3[C@H]([C@H]([C@@H](O3)CO)O)O)Cl)Cl
• Recent ClinicalTrials: A Study of Maribavir Compared to Valganciclovir to Treat Cytomegalovirus Infections in People Who Have Received Stem Cell Transplants
• Recent EU Clinical Trials: A Phase 3, open-label, single-arm, repeated-dose study to evaluate the
• Recent NIPH Clinical Trials: A Study of Maribavir in Japanese People with Cytomegalovirus (CMV) Infection
• Description: Maribavir is an orally bioavailable benzimidazole L-riboside antiviral, with a spectrum of activity essentially limited to human cytomegalovirus (CMV) and Epstein–Barr virus (EBV). It is an inhibitor of the CMV UL97 kinase. As of 2008, maribavir was in phase III clinical trials for prevention of CMV infection in transplant recipients at risk. Earlier phase I and II trials of maribavir showed anti-CMV activity with an acceptable adverse effect profile. Investigational drug code names include 1263W94, BW1263-W94, GW257406X, and VP41263, reflecting changes in ownership during drug development. As of early 2009, the drug was being developed under ‘‘fast track’’ status granted by the US Food and Drug Administration, but the apparent failure of maribar prophylaxis to prevent CMV infection in stem cell transplant recipients in the definitive phase III clinical trial resulted in the sponsor halting ongoing clinical development.
• Uses: Treatment of cytomegalovirus infections (antiviral).
• Drug interactions: Since CYP3A4 appears to be the major maribavir-metabolizing enzyme, there are potential drug interactions with CYP3A4 inhibitors, such as azole antifungals, macrolide antibiotics, and HIV protease inhibitors, or CYP3A4 inducers, such as rifampicin or efavirenz. There are insufficient data to assess the clinical significance of this interaction. Phase I clinical trials examined the pharmacokinetics of maribavir in HIV-infected subjects, many of whom were concomitantly using antifungals and protease inhibitors. Overall, the pharmacokinetic data were not significantly different from those of healthy individuals not on these drugs. In healthy adults, oral administration of ketoconazole, a potent CYP3A4 inhibitor, resulted in a 35% decrease in the clearance of maribavir, which is not expected to have adverse consequences because of the low observed toxicity of maribavir. Further studies are required to assess potential impairment of antiviral activity by CYP3A4 inducers. Maribavir may have some inhibitory effect on cytochrome P450 isozymes, CYP2C19 and CYP2D6, as assessed after administration of multiple concurrently administered drug probes, including omeprazole (2C19) and dextromethorphan (2D6).

Technology Process of Maribavir

There total 30 articles about Maribavir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

isopropylamine (75-31-0) + 2,3'-O-anhydro-5,6-dichloro-1-(β-L-lyxofuranosyl)benzimidazole (220007-81-8) → 5,6-dichloro-2-isopropylamino-1-(β-L-lyxofuranosyl)benzimidazole (176161-24-3)

Guidance literature:

In ethanol; at 70 - 80 ℃; for 336h;

DOI:10.1021/jo981733t

Reference yield: 64.0%

isopropylamine (75-31-0) + 1-(α-D-lyxofuranosyl)-2,5,6-trichlorobenzimidazole (202119-42-4) → 1-(α-D-lyxofuranosyl)-2-isopropylamino-5,6-dichloro-benzimidazole (176161-24-3)

Guidance literature:

In ethanol; at 70 ℃; for 48h;

DOI:10.1021/jm970545c

Reference yield: 63.0%

isopropylamine (75-31-0) + UMJD853 (202119-41-3) → 1-(α-L-lyxofuranosyl)-2-isopropylamino-5,6-dichloro-benzimidazole (176161-24-3)

Guidance literature:

In ethanol; at 70 ℃; for 48h;

DOI:10.1021/jm970545c

upstream raw materials:

isopropylamine

UMJD₈₅₃

1-(2,3,5-tri-O-acetyl-α-L-lyxofuranosyl)-2,5,6-trichlorobenzimidazole

2,5,6-trichloro-1H-benzo[d]imidazole

Refernces

• 1、 -. "Crystalline forms of an antiviral benzimidazole compound". Page/Page column 14-15. . Retrieved 2015/11/10.
• 2、 -. "Form vi 5,6-dichloro-2-(isopropylamino)-1-(β-l-ribofuranosyl)-1h-bezimimidazole". . . Retrieved 2008/06/13.