Dactimicin
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| Category | Antibiotics |
| Catalog number | BBF-00775 |
| CAS | 73196-97-1 |
| Molecular Weight | 432.51 |
| Molecular Formula | C18H36N6O6 |
| Purity | >98% |
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Description
Dactimicin is an aminoglycoside antibiotic produced by Dactilosporangium matsuzakiense SF-2O52. It has anti-gram-positive and negative bacteria activity.
Specification
| Related CAS | 103531-05-1 |
| Synonyms | SF-2052 |
| Storage | Store at -20°C |
| IUPAC Name | N-[4-amino-3-[3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-2,5-dihydroxy-6-methoxycyclohexyl]-2-(aminomethylideneamino)-N-methylacetamide |
| Canonical SMILES | CC(C1CCC(C(O1)OC2C(C(C(C(C2O)N(C)C(=O)CN=CN)OC)O)N)N)N |
| InChI | InChI=1S/C18H36N6O6/c1-8(20)10-5-4-9(21)18(29-10)30-16-12(22)14(26)17(28-3)13(15(16)27)24(2)11(25)6-23-7-19/h7-10,12-18,26-27H,4-6,20-22H2,1-3H3,(H2,19,23) |
| InChI Key | VFBPKQSATYZKRX-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 658.9°C at 760 mmHg |
| Solubility | Soluble in DMSO |
Reference Reading
1. Dactimicin, a new aminoglycoside: in vitro activity, post-antibiotic effect and interaction with other antibiotics
P Paglia, G Molinari, A Pesce, E A Debbia Eur J Clin Microbiol Infect Dis. 1989 Jul;8(7):639-43. doi: 10.1007/BF01968148.
The in vitro activity of the new aminoglycoside dactimicin in comparison to amikacin was tested alone and in combination with piperacillin, mezlocillin and ceftazidime against freshly isolated clinical pathogens. Dactimicin was more active than amikacin against Enterobacter cloacae, Providencia rettgeri and Salmonella spp., and less active than amikacin against Escherichia coli, Pseudomonas aeruginosa and Acinetobacter anitratus. Using the checkerboard technique, the combination of either dactimicin or amikacin with the other drugs was shown to result in synergistic interaction against most of the 23 strains tested. Dactimicin-ceftazidime and amikacin-ceftazidime were the most effective combinations, demonstrating synergism against 91% and 95% of the isolates respectively. Antagonism was not encountered. Using the time-kill method, synergism was seen in most cases, indifference rarely being seen; antagonism was not observed. Dactimicin induced a post-antibiotic effect which ranged from 1 h for Enterobacter cloacae to 2.4 h for Escherichia coli. An average post-antibiotic effect of 0.6 h was also seen when dactimicin was combined with piperacillin, mezlocillin and ceftazidime. The findings indicate that dactimicin compares favorably in vitro with amikacin and suggest that clinical trials with this drug alone or in combination are warranted.
2. In vitro activity of dactimicin, a novel pseudodisaccharide aminoglycoside, compared with activities of other aminoglycosides
J W Gu, H C Neu Antimicrob Agents Chemother. 1989 Nov;33(11):1998-2003. doi: 10.1128/AAC.33.11.1998.
The in vitro activity of dactimicin, a new pseudodisaccharide aminoglycoside which possesses a formimidoyl group, was compared with those of gentamicin, tobramycin, and amikacin against 500 isolates. Dactimicin inhibited 90% of isolates from the family Enterobacteriaceae at a concentration of less than or equal to 4 micrograms/ml. It was more active than amikacin against Klebsiella pneumoniae, Serratia marcescens, Citrobacter diversus, Enterobacter agglomerans, Yersinia species, and Salmonella species, with an MIC for 90% of the strains (MIC90) of less than or equal to 4 micrograms/ml. The MIC90s for the Pseudomonas aeruginosa isolates were greater than 128 micrograms/ml. Dactimicin did not inhibit most methicillin-resistant Staphylococcus aureus isolates and coagulase-negative staphylococci but had an MIC50 (MIC for 50% of strains tested) of 2 micrograms/ml against methicillin-susceptible S. aureus isolates and coagulase-negative staphylococci. Dactimicin in combination with piperacillin acted synergistically against 75% of Escherichia coli, K. pneumoniae, S. marcescens, and S. aureus isolates. It exhibited an excellent postantibiotic suppressive effect on E. coli. Dactimicin was active against organisms possessing aminoglycoside-modifying enzymes including AAC(2')-b, AAC(3)-III, -IV, and -V, and AAC(6')-Ia, -Ib, Ic, -II, and -IV but was not active against isolates which contained AAC(3)-I and the bifunctional APH(2")-AAC(6')-I. Its lack of activity against P. aeruginosa appeared to be permeability related since in the presence of EDTA P. aeruginosa was susceptible, as were mutant isolates resistant because of permeability barriers.
3. In vitro activity of dactimicin and other aminoglycosides against bacteria producing aminoglycoside-modifying enzymes
D Felmingham, K Jones Drugs Exp Clin Res. 1989;15(3):133-6.
Dactimicin is a new pseudo-disaccharide aminoglycoside, originally isolated from cultures of Dactylosporangium matsuzakienzae sp. nov., which is chemically related to astromicin. In this study the in vitro activity of dactimicin has been determined against strains of bacteria producing characterized aminoglycoside-modifying enzymes and has been compared with that of gentamicin, tobramycin, netilmicin and amikacin. Minimum inhibitory concentrations were determined using an agar incorporation technique in Mueller-Hinton agar with an inoculum of approximately 10(4) cfu. Dactimicin was resistant to inactivation by a number of different acetyltransferases (AAC), produced by species of the Enterobacteriaceae, most of which inactivated gentamicin, tobramycin and netilmicin. The exception was an AAC(3')-I produced by an isolate of Escherichia coli, which inactivated gentamicin and dactimicin but not tobramycin, netilmicin and amikacin. Dactimicin was inactivated by the adenyltransferases (AAD) AAD(2") and AAD(9), produced by Pseudomonas aeruginosa, but not by an AAD(4')(4"), produced by a strain of Staphylococcus aureus, nor by an AAD(2") produced by a strain of E. coli. Dactimicin was inactivated by a combination of a phosphotransferase (APH) APH(2") and an AAC(6') produced by strains of S. aureus. The results suggest that dactimicin may retain useful antibacterial activity against many gentamicin-resistant strains of bacteria belonging to the Enterobacteriaceae and some gentamicin-resistant strains of S. aureus.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
