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6576-51-8

6576-51-8 Structure

6576-51-8 Structure
IdentificationBack Directory
[Name]

DISTAMYCIN A HYDROCHLORIDE
[CAS]

6576-51-8
[Synonyms]

fi6426
herperal
MEN-10399
DISTAMYCIN A HCL
estalimicinaclorhidrato
stallimycinhydrochloride
DISTAMYCIN A HYDROCHLORIDE
distamycin A hydrochloride from*streptomyces dist
DISTAMYCIN A HYDROCHLORIDE FROM*STREPTOM YCES DISTAL
Distamycin A hydrochloride from Streptomyces distallicus
N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-(formylamino)-1-me
N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-1H-pyrrole-2-carboxamide monohydrochloride
1H-Pyrrole-2-carboxaMide,N-[5-[[(3-aMino-3-iMinopropyl)aMino]carbonyl]-1-Methyl-1H-pyrrol-3-yl]-4-[[[4-(forMylaMino)-1-Methyl-1H-pyrrol-2-yl]carbonyl]aMino]-1-Methyl-,hydrochloride (1:1)
[EINECS(EC#)]

229-505-6
[Molecular Formula]

C22H28ClN9O4
[MDL Number]

MFCD00058165
[MOL File]

6576-51-8.mol
[Molecular Weight]

517.97
Chemical PropertiesBack Directory
[Melting point ]

184-187° (Arcamone, 1967). Also reported as 189-193° from ethanol-ethyl acetate (Bialer)
[storage temp. ]

−20°C
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

43
[Safety Statements ]

36/37
[WGK Germany ]

3
[RTECS ]

WZ7110000
[Toxicity]

LD50 in mice (mg/kg): 75 i.v.; 500 i.p. (DiMarco)
Hazard InformationBack Directory
[Originator]

Herperal,Farmitalia,Italy,1978
[Manufacturing Process]

A spore suspension obtained upon washing a culture of Streptomyces distallicus is added to 3,000 ml of a sterile medium consisting of the following:Dextrose 2% Corn steep liquor extract 2% CaCO3 1% (NH4)2SO4 0.3% NaCl 0.3%Fermentation is continued at 28°C for 40 hours at a stirring rate of 150 to 250 rpm and a rate of air flow of 1 to 2 l/min/l of culture medium.
300 ml of a suspension of the vegetative mycelium of this culture are used for inoculating 6,000 ml of a similar sterile culture medium. At this production stage, the culture is kept fermenting for 85 to 100 hours (pH 7.6 at 28°C) at a stirring rate of 350 to 450 rpm and a rate of air flow of 1 to 1.5 l/min/l of culture medium.
To 17 l of a culture obtained by submerged fermentation as mentioned above, siliceous earth is added and the batch is filtered. The mixture of mycelium and the siliceous earth are agitated for 1 hour with 2.5 l of butanol. This treatment is repeated twice. The butanolic extracts are combined, washed with water, evaporated to dryness (about 10 g) and boiled with acetone (80 ml). The 5 g of distamycin is extracted six times with ethanol. The ethanolic extracts are combined, concentrated and filtered through a column containing 70 g of alumina. Elution is carried out with the same solvent. The effluent (central fractions) is collected and evaporated to dryness to yield 0.43 g of pure distamycin A: decomposition point, 183°C to 185°C. The product can be further purified by crystallization from aqueous n-butanol.
[Therapeutic Function]

Antibiotic
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