Fortimicins A and B, new aminoglycoside antibiotics. I. Producing organism, fermentation a biological properties of fortimicins.

Nara, Takashi; Yamamoto, Masamichi; Kawamoto, Isao; Takayama, Kuni; Okachi, Ryo; Takasawa, Seigo; Sato, Tomoshige; Sato, Seiji

doi:10.7164/antibiotics.30.533

Cited by 112 publications

(34 citation statements)

References 25 publications

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“…1). This new aminoglycoside possesses antimicrobial activity similar to that of amikacin and kanamycin and markedly superior to that of the related derivative, fortimicin B (5,10).…”

mentioning

confidence: 99%

“…The structural qualities of fortimicin A protect it from most commonly encountered aminoglycoside-inactivating enzymes (10,12). Fortimicin A has signiicantly increased antimicrobial activity as compared to fortimicin B (10), but lacks the pseudomonas antimicrobial features common to amikacin, gentamicin, and tobramycin (5,10). Animal and human oto-renal toxicity has yet to be reported.…”

mentioning

confidence: 99%

“…DISCUSSION Fortimicin A and B are novel new disaccharide aminoglycosides produced by M. olivoasterospora (2,5,10,11). The structural qualities of fortimicin A protect it from most commonly encountered aminoglycoside-inactivating enzymes (10,12). Fortimicin A has signiicantly increased antimicrobial activity as compared to fortimicin B (10), but lacks the pseudomonas antimicrobial features common to amikacin, gentamicin, and tobramycin (5,10).…”

mentioning

confidence: 99%

“…The results of these studies are also'shown in Table 4. DISCUSSION Fortimicin A and B are novel new disaccharide aminoglycosides produced by M. olivoasterospora (2,5,10,11). The structural qualities of fortimicin A protect it from most commonly encountered aminoglycoside-inactivating enzymes (10,12).…”

mentioning

confidence: 99%

“…Fortamine cyclitol-containing antimicrobials were obtained from Micromonospora olivoasterospora (2,10,11). The most promising compound, fortimicin A (XK-70-1), is a novel pseudodisaccharide antibiotic with chiro cyclitol stereochemistry ( Fig.…”

mentioning

confidence: 99%

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Fortimicin A: collaborative in vitro susceptibility. Comparison with amikacin and gentamicin against 11,840 clinical bacterial isolates

Jones¹,

Barry²,

Fuchs³

et al. 1979

Antimicrob Agents Chemother

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The susceptibility of 11,840 clinical bacterial isolates to fortimicin A was determined by agar dilution or broth microdilution methods and compared with their susceptibility to amikacin and gentamicin. In general, the in vitro activity of fortimicin A was essentially the same as that of amikacin. Significant exceptions were the increased effectiveness of fortimicin A against Serratia marcescens and the greater activity of amikacin against Pseudomonas and other nonfermentative gram-negative bacilli. On a weight-for-weight basis, gentamicin showed greater activity than the other two antimicrobial drugs against most species; S. marcescens was the major exception. However, at concentrations equivalent to achievable nontoxic serum levels, the proportion of isolates inhibited by the three drugs was quite comparable. There were several strains with unusually high resistance to one or more of the tested antibiotics. These usually occurred in one of the six participating institutions and could be traced to specific enzyme-producing or permeability mutants endemic to that particular institution.

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“…1). This new aminoglycoside possesses antimicrobial activity similar to that of amikacin and kanamycin and markedly superior to that of the related derivative, fortimicin B (5,10).…”

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Fortimicin A: collaborative in vitro susceptibility. Comparison with amikacin and gentamicin against 11,840 clinical bacterial isolates

Jones¹,

Barry²,

Fuchs³

et al. 1979

Antimicrob Agents Chemother

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Aminoglycosides

Mcgregor

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Aminoglycosides are members of the class of antibacterial antibiotics, the structures of which are derived from D ‐streptamine, D ‐2‐deoxystreptamine, or closely related compounds. The term aminocyclitol is sometimes used to identify this group of compounds. In 1991, the most widely used aminoglycosides in medical practice were gentamicin, tobramycin, amikacin, and netilmicin. In general, the aminoglycosides are useful for the treatment of serious infections involving aerobic or facultative gram‐negative bacilli. The most common resistance mechanism involves the inactivation of the aminoglycoside by reactions catalyzed by plasmid‐borne enzymes. Less common resistance mechanisms include decreased affinity for the antibiotic by the bacterial ribosome and decreased rate of transport into the bacterial cytoplasm. The aminoglycosides are administered primarily by intravenous infusion or intramuscular injection. Most of the administered dose is eliminated unmetabolized in the urine. Potential toxicity is a primary limiting factor in the clinical use of aminoglycosides. The most important toxicities are nephrotoxicity, ototoxicity, and to a lesser extent, neuromuscular blockade. All the aminoglycosides in medical practice are capable of causing these adverse events. The effect of this potential is to prevent the use of significantly increased doses to cover difficult infections. The bactericidal mechanisms employed by aminoglycosides are incompletely understood. In the cytoplasm, ribosomal binding leads to misreading of the genetic code and production of abnormal proteins and protein synthesis inhibition. The cause of cell death is uncertain. A large amount of research has been conducted aimed at reducing the limitations in the areas of toxicity and susceptibility to bacterial resistance mechanisms while maintaining the advantages by modification of the aminoglycoside molecular structure. Overall, structural modification has been successful in reducing susceptibility to bacterial inactivation. It has not been possible, however, to substantially dissociate the toxicity potential from the antibacterial activity.

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Totalsynthese eines Fortimicin‐Aglycons

1984

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saureethylester) trennen: Ausbeute an 4 60-700h. Zur Umwandlung in 5 werden 4.2 g 4 unter CO mit Natriumamalgam (0.2 g Na in 40 g Hg) in 100 mL THF umgesetzt (Farbllnderung griin+braun thylamino)-methyliminophosphoran[81 (Acetonitril, 60"C, 3 h), regiospezifisch unter Angriff an C-1 zum Oxazolidon rac-5a cyclisiert. Die a priori nicht unwahrscheinliche K o n k~r r e n z~~~ des Angriffs an C-2 ist in keinem Fall nachweisbar (< 2%). In Kauf genommen werden muD allerdings die ,,Umesterung" zum Gemisch der vier Komponenten roc-5a-d (zusammen 97%). Nach Verseifung mit Natriumethanolat/Ethanol (60"C, 1.5 h) isoliert man reines rac-56 (72-75%, Fp= 152-155°C (nicht optimiert), daneben bis zu 5% des Adduktes von C2H50e an C-3)['01. Eher gliickhaft als erwartet ist die Spezifitiit, mit der der Halbsessel rac-5d (DZ0,J3.4=1.0, 54,5=4.0, J5,6==3.5 Hz) an C-3

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Fortimicins A and B, new aminoglycoside antibiotics. I. Producing organism, fermentation a biological properties of fortimicins.

Cited by 112 publications

References 25 publications

Fortimicin A: collaborative in vitro susceptibility. Comparison with amikacin and gentamicin against 11,840 clinical bacterial isolates

Fortimicin A: collaborative in vitro susceptibility. Comparison with amikacin and gentamicin against 11,840 clinical bacterial isolates

Aminoglycosides

Totalsynthese eines Fortimicin‐Aglycons

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