Freselestat
Basic information
- CAS
208848-19-5- Standard SMILES
CC(C)C(NC(=O)Cn1c(-c2ccccc2)ncc(N)c1=O)C(=O)c1nnc(C(C)(C)C)o1- InChIKey
YSIHYROEMJSOAS-UHFFFAOYSA-N- Molecular formula
- C23H28N6O4
- Average molar mass
- 452.5 g/mol
- Monoisotopic mass
- 452.2172034
Names & identifiers
- Preferred name
- Freselestat
- IUPAC
- 2-(5-amino-6-oxo-2-phenylpyrimidin-1-yl)-N-[1-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-3-methyl-1-oxobutan-2-yl]acetamide
- English name
- FRESELESTAT
- Molecular formula
- C23H28N6O4
- Molecular weight
- 452.51
Names & synonyms
Freselestat208848-19-5ono-6818Freselestat [INN]1CW4RL23VPUNII-1CW4RL23VPONO-PO 7361(6H)-Pyrimidineacetamide, 5-amino-N-[1-[[5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2-yl]carbonyl]-2-methylpropyl]-6-oxo-2-phenyl-2-(5-Amino-6-oxo-2-phenylpyrimidin-1(6H)-yl)-N-((1RS)-1-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-3-methyl-1-oxobutan-2-yl)acetamide1(6H)-Pyrimidineacetamide, 5-amino-N-(1-((5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2-yl)carbonyl)-2-methylpropyl)-6-oxo-2-phenyl-freselestatum2-(5-amino-6-oxo-2-phenyl-1,6-dihydropyrimidin-1-yl)-N-((1R,2R)-1-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-hydroxy-3-methylbutan-2-yl)acetamide
Show more names
ONO6818FreselesatONO-PO-736Freselestat (ONO-6818)1(6H)-PyriMidineacetaMide,5-aMino-N-[1-[[5-(1,1-diMethylethyl)-1,3,4-oxadiazol-2-yl]carbonyl]-2-Methylpropyl]-6-oxo-2-phenyl-
2-(5-amino-6-oxo-2-phenyl-1,6-dihydropyrimidin-1-yl)-N-[(1R,2R)-1-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-1-hydroxy-3-methylbutan-2-yl]acetamideRefChem:141534Ono 68182-(5-amino-6-oxo-2-phenylpyrimidin-1-yl)-N-[1-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-3-methyl-1-oxobutan-2-yl]acetamideCHEMBL258925-Amino-N-[1-[[5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2-yl]carbonyl]-2-methylpropyl]-6-oxo-2-phenyl-1(6H)-pyrimidineacetamideONO-6818;ONO-PO-736;ONO6818;ONO 68185-Amino-N-[1-[[5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2-yl]carbonyl]-2-methylpropyl]-6-oxo-2-phenyl-1(6H)-pyrimidineacetamide; ONO 6818; ONO-PO 736
Database identifiers
- CAS
208848-19-5- PubChem CID
- 216294
- DTXSID
DTXSID50943150- ChEMBL
CHEMBL25892- UNII
- 1CW4RL23VP
- Nikkaji
- J1.647.741I
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 144 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 8
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 825
Physicochemical properties
- Melting point
- 151 · 151-153oC
- Density
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 12.43 · 12.43±0.46(Predicted)
- form
- Solid
- color
- Off-White to Pale Yellow
- FDA UNII
- 1 CW4RL23VP · 1CW4RL23VP
Chemistry & industry
Pharmacology
Mechanism of Action
ONO-6818 inhibits neutrophil elastase activity, reducing interleukin 8 production and the formation of the complement membrane attack complex. Consequently, neutrophil elastase levels are reduced during stimulated extracorporeal circulation.
Applications
UsesFreselestat is a highly potent nonpeptidic orally active inhibitor of human neutrophil elastase (HNE) and can be used as treatment for neutrophil-predominant inflammatory lung diseases.
Related reactions
1 records
Compound notes
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