DESCRIPTIONS OF ANTIBIOTICS 



369 



Utilization: Staphylococcal infections resistant 

 to other antibiotics (5). 

 References: 



1. DeSomer, P. and Van Dijck, P. Antibiotics 



& Chemotherapy 5: 632-639, 1955. 



2. Vanderhaeghe, H. et al. Antibiotics & 



Chemotherapy 7:606-614,1957. 



3. Van Dijck, P. et al. Antibiotics & Chemo- 



therapy 7: 625-629. 1957. 



4. Arai, M. et al. J. Antibiotics (Japan) llA: 



21-25, 1958. 



5. DeSomer, P. and Van der Voorde, H. Anti- 



biotic Med. & Clin. Therapy 4: 786-797, 

 1957. 



6. Ball, D. et al. Biochem. J. 68: 24, 1958. 



7. Vanderhaeghe, H. and Parmentier, G. 



J. Am. Chem. Soc. 82: 4414-4422, 1960. 



Slreptimidoiie 



Froduced by: Streptomyces riinosus f. parumo- 

 Diycinus, which also produces paromomycin. 



Method of extraction: Extraction of the culture- 

 filtrate at pH 5.0 with ethyl acetate. Washing of 

 the concentrated extract with dilute aqueous so- 

 dium carbonate, dilute acid, and water. Precipita- 

 tion of the crude streptimidone from ethyl ace- 

 tate with petroleum ether. Chromatography of 

 the precipitated crude antibiotic on activated 

 carbon from acetone solution. Crystallization 

 from an acetone-isopropanol-ether solution. 



Chemical and physical properties: Fine colorless 

 needles; m.p. 72-73°C. Soluble in methanol, ethanol, 

 acetone, ethyl acetate, and chloroform. Slightly 

 soluble in water and ethyl ether. Insoluble in pe- 

 troleum ether. Most stable at pH 4.5. Destroyed 

 by exposure to sunlight. C16H23NO4 . [a]" = +238° 

 (c = 0.5 per cent in water), [a]^^ = +245° (c = 

 0.5 per cent in chloroform). Light-absorption 

 maxima at 232 and 291 m/j. (methanol) ; 231 and 289 

 m^t (water). Infrared absorption spectrum given in 

 reference 1. Bromine and aqueous permanganate 

 solutions decolorized. Positive m-phenylenedi- 

 amine test for Qr,/3-unsaturated aldehydes and ke- 

 tones. Positive sodium nitroprusside test for 

 methyl ketones. Negative ninhydriii, periodate, 

 Tollen, and titanium chloride tests. Structure de- 

 termined (see Chapter 6). Streptimidone is 3(2- 

 hydroxy-7-methyl-5-methylene-4-oxo-6-nonenyl) 

 glutarimide (1). A somewhat different formula has 

 recently been proposed (3). 



Biological activity: Active against yeasts, fila- 

 mentous fungi, and protozoa. Slight activitj^ 

 against certain bacteria. Has herbicidal activity. 

 Effective against amebic dysentery in dogs. 



Toxicity: LDjo (mice) 192 mg per kg intrave- 

 nously. Chronic toxicity in animals is high. 



References: 



1. Frohardt, R. P. et al. J. Am. Chem. Soc. 



81: 5500-5506, 1959. 



2. Kohberger, D. L. et al. Antibiotics & Chem- 



otherapy 10:9-16,1960. 



3. van Tamelen, E.E. et al. J. Am. Chem. Soc. 



82: 2974, 1960. 



Streptin 



Produced by: Streptomyces sp. resembling S. 

 relic id us -ruber (2). 



Synonym: Similar to streptothricin (1, 2). 



Method of extraction: Like that for streptothricin 

 (1,2). 



Chemical and- physical properties: Basic sub- 

 stance. Soluble in water, acid, alcohol, and dilute 

 acids. Insoluble in ether, chloroform, and acetone. 

 Thermostable (2). 



Biological activity: Qualitatively the same as 

 streptothricin, but more active on a weight basis 

 (2). 



References: 



1. Woodruff', H. B. and Foster, J. W. J. Bac- 



teriol. 52: 502, 1946. 



2. British Patent 644,582, October 11, 1950. 



Streplocardin 



Produced by: Streptomyces sp. and Nocardia sp. 



Method of extraction: Extraction of the culture- 

 filtrate with ether at pH 4.0. Back-extraction in 

 pH 7.0 phosphate buffer. Extraction in ether at 

 pH 4.0. Concentration of ether in vacuo; residue 

 dissolved in acetone; concentration to dryness. 

 Crystallization from ether solutions. 



Chemical and physical properties: Acidic sub- 

 stance, soluble in many organic solvents. Brown 

 needles. Alkali salts are soluble in water. Ultra- 

 violet light-absorption maxima at 365 niju (£'i°cm 

 187) with a shoulder at 242 to 252 ni/x. 



Biological activity: Active against gram-positive 

 bacteria, including mycobacteria, and gram-nega- 

 tive bacteria. No activity against the fungi tested. 



Toxicity: LD50 (mice) 12.5 mg per kg intra- 

 venously. 



Reference: 1. Fisher, W. P. et al. Antil)iotics 

 Ann. 1953-1954, pp. 177-178. 



Streptocin 



Produced by: Streptomyces griseus strains. The 

 original streptocin-producer formed other anti- 

 biotics, including what was believed to be cyclo- 

 heximide, as well as an antibiotic which was highly 

 active on Sarcinalutea. Streptocin is also formed 

 by strains of S. griseus that produce grisein and 

 streptomycin (1, 2). 



