Page last updated: 2024-12-06

flurithromycin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Flurithromycin is a macrolide antibiotic used to treat bacterial infections. It is a semi-synthetic derivative of erythromycin, with a fluorine atom added to the 9-position. Flurithromycin exhibits improved pharmacokinetic properties compared to erythromycin, including increased bioavailability and a longer half-life. Its mechanism of action involves binding to the 50S ribosomal subunit of bacteria, inhibiting protein synthesis. Flurithromycin is effective against a wide range of gram-positive bacteria, including Streptococcus pneumoniae, Staphylococcus aureus, and Haemophilus influenzae. It is also active against some gram-negative bacteria, such as Moraxella catarrhalis. Research on flurithromycin focuses on its efficacy in treating various infections, its pharmacokinetic properties, and its potential for drug interactions.'

flurithromycin: fluorine derivative of erythromycin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

flurithromycin : 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is erythromycin A in which the hydrogen attached to the carbon at position 8 (alpha to the ketone carbonyl group) has been replaced by a fluorine.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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID71260
CHEMBL ID2106403
CHEBI ID131719
SCHEMBL ID135737
MeSH IDM0133315

Synonyms (38)

Synonym
(3r,4s,5s,6r,7r,9s,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-9-fluoro-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxa
flurithromycin
ci-932
8-fluoroerythromycin
flurizic
mizar
p-0501-a
erythromycin, 8-fluoro-
fluritromycinum [latin]
(8s)-8-fluoroerythromycin
flurithromycin [inn]
flurithromycine [french]
cl-932
p 80206
p-0501a
(8s)-8-fluoroerythromycin a
antibiotic p 80206
fluritromicina [spanish]
flurithromycin (inn)
D07242
CHEBI:131719
(3r,4s,5s,6r,7r,9s,11r,12r,13s,14r)-6-{[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2h-pyran-2-yl]oxy}-14-ethyl-9-fluoro-7,12,13-trihydroxy-4-{[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2h-pyran-2-yl]oxy}-3,5,7,9,11,13-hexa
fluritromicina
flurithromycine
flurithromycinum
fluritromycinum
unii-56c9dte69v
56c9dte69v ,
CHEMBL2106403
SCHEMBL135737
flurithromycin [who-dd]
flurithromycin [mi]
XOEUHCONYHZURQ-HNUBZJOYSA-N
DTXSID40905085
Q5462893
DB13338
CS-0027000
HY-106959

Research Excerpts

Overview

Flurithromycin is an (8,S)-8-fluoroerythromycin isolated from the fermentation broth of Streptomyces erythraeus ATCC 31772.

ExcerptReferenceRelevance
"Flurithromycin is an (8,S)-8-fluoroerythromycin isolated from the fermentation broth of Streptomyces erythraeus ATCC 31772, a blocked mutant of a strain producer of erythromycin. "( In vitro activity of flurithromycin, a novel macrolide antibiotic.
Alesina, R; Bersani, C; Ferrara, A; Fietta, A; Gialdroni Grassi, G; Peona, V, 1986
)
2.03

Effects

ExcerptReferenceRelevance
"Flurithromycin has promising antibacterial activity which warrants clinical trials."( Comparative antimicrobial activity of the new macrolide flurithromycin against respiratory pathogens.
Lindmark, A; Nord, CE; Persson, I, 1988
)
1.24

Toxicity

ExcerptReferenceRelevance
" EF was not cytotoxic after 18 h incubation at concentrations up to 8 X 10(-4) M and EE was much more toxic than EB at all concentrations studied."( Erythromycin toxicity in primary cultures of rat hepatocytes.
Bégué, JM; Guillouzo, A; Villa, P,
)
0.13

Pharmacokinetics

ExcerptReferenceRelevance
" The results of the pharmacokinetic study suggest that accumulation of the drug during repetitive multiple doses is predictable."( Pharmacokinetics and human tissue penetration of flurithromycin.
Benoni, G; Bertrand, C; Consolo, U; Cuzzolin, L; Ferronato, G; Fracasso, ME; Leone, R; Puchetti, V, 1988
)
0.53

Dosage Studied

ExcerptRelevanceReference
"The effects of a new fluorinated macrolide (P-0501A) on drug metabolizing enzymes of rat liver were compared with three erythromycins--the base, the stearate and the estolate--after 7 days of dosing (1."( Effects of a new fluorinated macrolide (P-0501A) and other erythromycins on drug metabolizing enzymes in rat liver.
Bartosek, I; Casacci, F; Corti, F; De Marchi, F; Guaitani, A; Pacei, E; Villa, P, 1986
)
0.27
" These results suggest that flurithromycin can inhibit the conversion of CBZ to CBZ-E, although, at the dosage tested, the magnitude of this effect was significantly smaller than that observed after administration of erythromycin in the same subjects."( Effect of flurithromycin, a new macrolide antibiotic, on carbamazepine disposition in normal subjects.
Amione, C; Barzaghi, N; Crema, F; Faja, A; Gatti, G; Leone, L; Monteleone, M; Perucca, E, 1988
)
0.97
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antibacterial drugA drug used to treat or prevent bacterial infections.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
erythromycin derivative
organofluorine compoundAn organofluorine compound is a compound containing at least one carbon-fluorine bond.
cyclic ketone
semisynthetic derivativeAny organic molecular entity derived from a natural product by partial chemical synthesis.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (43.75)18.7374
1990's11 (34.38)18.2507
2000's7 (21.88)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.17

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index22.17 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.22 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.17)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (8.33%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (2.78%)4.05%
Observational0 (0.00%)0.25%
Other32 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]