Brincidofovir sodiumProduct ingredient for Brincidofovir
- Name
- Brincidofovir sodium
- Drug Entry
- Brincidofovir
Brincidofovir is an oral antiviral drug used in the treatment of human smallpox infections. It is a lipid conjugate pro-drug of the acyclic nucleotide analogue cidofovir7,3 - this lipid conjugate improves drug delivery to the target cells and significantly reduces the nephrotoxicity typically associated with cidofovir therapy.3,4 Due to its formulation as a pro-drug brincidofovir also carries a greater bioavailability than cidofovir,5,3 allowing for oral administration rather than intravenous. Cidofovir itself has broad antiviral activity against several DNA viruses,3 resulting in brincidofovir being investigated for the prevention and treatment of cytomegalovirus (CMV), BK Virus (BKV), adenoviruses (AdV), and Epstein-Barr virus (EBV), amongst others.
Brincidofovir, developed by Chimerix under the brand name Tembexa, was approved by the FDA for the treatment of smallpox infection in June 2021.8 As smallpox has been eradicated, the efficacy of Tembexa was assessed in animals infected with viruses closely related to variola. The approval was granted under the agency’s Animal Rule,9 which allows for a drug to be approved based on the results of well-controlled animal studies when human trials would be unethical or infeasible.
- Accession Number
- DBSALT002145
- Structure
- Synonyms
- Not Available
- UNII
- 8UN8SA9Z5C
- CAS Number
- 496765-79-8
- Weight
- Average: 583.683
Monoisotopic: 583.33623227 - Chemical Formula
- C27H51N3NaO7P
- InChI Key
- CRDDLOITBKEPRN-UQIIZPHYSA-M
- InChI
- InChI=1S/C27H52N3O7P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-35-20-16-21-37-38(33,34)24-36-25(23-31)22-30-18-17-26(28)29-27(30)32;/h17-18,25,31H,2-16,19-24H2,1H3,(H,33,34)(H2,28,29,32);/q;+1/p-1/t25-;/m0./s1
- IUPAC Name
- sodium 3-(hexadecyloxy)propyl ({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonate
- SMILES
- [Na+].CCCCCCCCCCCCCCCCOCCCOP([O-])(=O)CO[C@H](CO)CN1C=CC(N)=NC1=O
- External Links
- ChemSpider
- 21259112
- Predicted Properties
Property Value Source Water Solubility 0.00125 mg/mL ALOGPS logP 5.04 ALOGPS logP 4.42 Chemaxon logS -5.7 ALOGPS pKa (Strongest Acidic) 1.32 Chemaxon pKa (Strongest Basic) 4.66 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 146.74 Å2 Chemaxon Rotatable Bond Count 26 Chemaxon Refractivity 148.78 m3·mol-1 Chemaxon Polarizability 65.81 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon