Brincidofovir

Base Information

• Chemical Name: Brincidofovir
• CAS No.: 444805-28-1
• Molecular Formula: C27H52N3O7P
• Molecular Weight: 561.69100
• UNII: 6794O900AX
• DSSTox Substance ID: DTXSID60196190
• Nikkaji Number: J2.075.976C
• Wikipedia: Brincidofovir
• Wikidata: Q15411004
• NCI Thesaurus Code: C90587
• RXCUI: 2599518
• Metabolomics Workbench ID: 144511
• ChEMBL ID: CHEMBL203321
• Mol file: 444805-28-1.mol

Synonyms:brincidofovir;cidofovir hexadecyloxypropyl ester;CMX 001;CMX-001;CMX001;HDP-CDV;hexadecyloxypropyl cidofovir;Tembexa

Chemical Property of Brincidofovir

Chemical Property:

• Melting Point: > 177° C (dec.)
• Boiling Point: 688.6±65.0 °C(Predicted)
• PKA: 2.40±0.10(Predicted)
• PSA: 156.93000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 5.59290
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly, Sonicated), Ethanol (Slightly, Heated, Sonicated), Methanol (Sli
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 26
• Exact Mass: 561.35428800
• Heavy Atom Count: 38
• Complexity: 721

Purity/Quality:

98% min ^*data from raw suppliers

Brincidofovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CCCCCCCCCCCCCCCCOCCCOP(=O)(COC(CN1C=CC(=NC1=O)N)CO)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCOCCCOP(=O)(CO[C@@H](CN1C=CC(=NC1=O)N)CO)O
• Recent ClinicalTrials: Study to Confirm of the Safety and Tolerability of Brincidofovir in Subjects With BK Virus Infection (Viremia) After Kidney Transplantation
• Recent EU Clinical Trials: A Randomized, Controlled, Open-Label, Multiple Ascending Dose Study of Intravenous Brincidofovir in Adult Allogeneic Hematopoietic Cell Transplant Recipients with Adenovirus Viremia
• Uses: Brincidofovir is an antiviral inhibitor, working against BK polymavirus replication in primary human urothelial cells. Cytostatic, cytotoxic agent.

Technology Process of Brincidofovir

There total 14 articles about Brincidofovir 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: 70.0%

N4-monomethoxytrityl-O3'-trityl-cidofovir, hexadecyloxypropyl ester (864068-46-2) → hexadecyloxypropyl-cidofovir (444805-28-1)

Guidance literature:

With acetic acid; In water; at 55 ℃;

Reference yield:

1-O-hexadecyloxypropyl cyclic cidofovir (343248-25-9) → hexadecyloxypropyl-cidofovir (444805-28-1)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 1.5h;

DOI:10.1128/AAC.46.4.991-995.2002

Reference yield:

phosphonic acid [[(S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)-2-(triphenylmethoxy)ethyl]methyl]mono[3-(hexadecyloxy)propyl]ester (1362039-08-4) → hexadecyloxypropyl-cidofovir (444805-28-1)

Guidance literature:

phosphonic acid [[(S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)-2-(triphenylmethoxy)ethyl]methyl]mono[3-(hexadecyloxy)propyl]ester; With hydrogenchloride; In methanol; N,N-dimethyl-formamide; at 5 - 18 ℃; Industry scale;

With sodium hydroxide; In methanol; water; N,N-dimethyl-formamide; pH=2.3 - 2.7; Product distribution / selectivity;

upstream raw materials:

1-O-hexadecyloxypropyl cyclic cidofovir

1-(hexadecyloxy)-3-bromopropane

cyclic cidofovir

cidofovir

Refernces

• 1、 Beadle, James R.,Hartline, Caroll,Aldern, Kathy A.,Rodriguez, Natalie,Harden, Emma,Kern, Earl R.,Hostetler, Karl Y.. "Alkoxyalkyl esters of cidofovir and cyclic cidofovir exhibit multiple-log enhancement of antiviral activity against cytomegalovirus and herpesvirus replication in vitro". . p. 2381 - 2386. Retrieved 2002.
• 2、 -. "Phosphonate Ester Derivatives and Methods of Synthesis Thereof". Page/Page column 22-23. . Retrieved 2012/03/26.
• 3、 -. "COMPOUNDS, COMPOSITIONS AND METHODS FOR THE TREATMENT OF VIRAL INFECTIONS AND OTHER MEDICAL DISORDERS". Page/Page column 45. . Retrieved 2008/06/13.