Flurithromycin

ChEBI: An erythromycin derivative that is erythromycin A in which the hydrogen attached to the carbon at position 8 (alpha to the ketone carbonyl group) has been replaced by a fluorine. It has been used (generally as the corresponding monoethyl s ccinate ester) as an antibacterial drug.

Flurithromycin is an erythromycin derivative that is erythromycin A in which the hydrogen attached to the carbon at position 8 (alpha to the ketone carbonyl group) has been replaced by a fluorine. It has been used (generally as the corresponding monoethyl succinate ester) as an antibacterial drug. It has a role as an antibacterial drug. It is an erythromycin derivative, an organofluorine compound, a cyclic ketone and a semisynthetic derivative. It derives from an erythromycin A.

Method 1: After inoculation with microorganisms (Streptomyces erythraeus, ATCC31772) for 24h, add 500μg/ml of (8S)-8-fluoroerythionolide A, and continue culturing for 96h. After 120h, it reaches the maximum value. Take 2.1L of culture medium [to which 1.0g of (8S)-8-fluoroerythionolide A is added] and filter. Add an equal volume of 10% aqueous solution of zinc sulfate and 4% aqueous solution of sodium hydroxide to the filtrate. After centrifugation, the upper clear solution was extracted with ethyl acetate with Ph value of 9.8. The extract was washed with water and dried over anhydrous sodium sulfate. Ethyl acetate was distilled off under reduced pressure to obtain 1.36 g of residue. Separation by partition column chromatography gave 0.35 g of fluorerythromycin. Recrystallized with ethanol to obtain 0.230g pure product, prismatic crystals, melting point 183 ~ 184 ℃. Method 2: Erythromycin is dehydrated under the action of acid to produce 8, 9-anhydroerythromycin-6, 9-hemiketal derivative, which is then oxidized to a tertiary amine oxide compound, and then trifluoromethyl hypofluorite or The reaction of fluoroperchloric acid introduces fluorine at the 8-position, and finally catalyzes the hydrogenolysis of N-oxide to obtain fluoroerythromycin.

A fluorinated derivative of Erythromycin (E649950). A macrolide antibiotic.

Molecular Weight:751.9
XLogP3:2.8
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:7
Exact Mass:751.45181932
Monoisotopic Mass:751.45181932
Topological Polar Surface Area:194
Heavy Atom Count:52
Complexity:1230
Defined Atom Stereocenter Count:18
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes