Structure via PubChem · Public domain (PubChem)
flurithromycin
Sign in to saveAlso known as antibiotic P 80206, P-0501A, P 80206, Cl-932, 8-fluoroerythromycin, (8S)-8-fluoroerythromycin A
Flurithromycin is a second generation macrolide antibiotic. It is a fluorinated derivative of erythromycin A. It is a broad spectrum antibiotic with similar bactericidal action to erythromycin. Unlike erythromycin, flurithromycin is more tolerant of acidic environments, meaning more survives the digestion process, resulting in higher serum levels, and more efficacious elimination of susceptible bacteria, including staphylococcus aureus and streptococcus pyogenes.
Chemical data
- Formula
- C37H66FNO13
- Molecular weight
- 751.9 g/mol
- IUPAC name
- (3R,4S,5S,6R,7R,9S,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-9-fluoro-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
- SMILES
- CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)(C)F)C)O)(C)O
- InChIKey
- XOEUHCONYHZURQ-HNUBZJOYSA-N
- XLogP
- 2.8
- Polar surface area
- 194 Ų
- H-bond donors
- 5
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- bacterial disease
via ChEMBL · EBI
Research
47 papers- Flurithromycin-induced acute interstitial nephritis.The Pediatric infectious disease journal · 2000
- Flurithromycin ethylsuccinate in the treatment of lower respiratory tract bacterial infections.Infection · 1994
- Antibacterial profile of flurithromycin, a new macrolide.The Journal of antimicrobial chemotherapy · 1992
- Analysis of macrolide antibiotics.Journal of chromatography. A · 1998
- Levels of flurithromycin in female genital tissue.Antimicrobial agents and chemotherapy · 1995
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 751.452
Show 5 more facts
- chemical formula
- C₃₇H₆₆FNO₁₃
- canonical SMILES
- CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)(C)F)C)O)(C)O
- isomeric SMILES
- CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)(C)F)C)O)(C)O
- World Health Organisation international non-proprietary name
- flurithromycin
- subject has role
- enzyme inhibitor
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Flurithromycin is a second generation macrolide antibiotic. It is a fluorinated derivative of erythromycin A. It is a broad spectrum antibiotic with similar bactericidal action to erythromycin. Unlike erythromycin, flurithromycin is more tolerant of acidic environments, meaning more survives the digestion process, resulting in higher serum levels, and more efficacious elimination of susceptible bacteria, including staphylococcus aureus and streptococcus pyogenes.
== References ==
Excerpted from Wikipedia’s “flurithromycin” article, available under the CC BY-SA 4.0 licence.