| Identification | Back Directory | [Name]
TYROTHRICIN | [CAS]
1404-88-2 | [Synonyms]
tyri10
tyroderm
coltirot
martricin
soluthricin
solutricine
bactratycin
TYROTHRICIN
Tyrothricine
dermotricine
hydrotricine
duboscrudecrystals
intradermtyrothricin
tyrothricin from bacillus aneurinolyticus (bacillus brevis)
3-[(3R,6S,9S,12S,15S,17S,20S,22R,25S,28S)-20-(2-amino-2-keto-ethyl)-9-(3-aminopropyl)-3,22,25-tris(benzyl)-15-(4-hydroxybenzyl)-6-isobutyl-12-isopropyl-2,5,8,11,14,18,21,24,27-nonaketo-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan-17-yl]propionic acid
3-[(3R,6S,9S,12S,15S,17S,20S,22R,25S,28S)-20-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,18,21,24,27-nonaoxo-3,22,25-tris(phenylmethyl)-12-propan-2-yl-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan-17-yl]propanoic acid
3-[(3R,6S,9S,12S,15S,17S,20S,22R,25S,28S)-20-(2-azanyl-2-oxo-ethyl)-9-(3-azanylpropyl)-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,18,21,24,27-nonaoxo-3,22,25-tris(phenylmethyl)-12-propan-2-yl-1,4,7,10,13,16,19,23,26-nonazabicyclo[26.3.0]hentriacontan-17-yl]propanoic acid | [EINECS(EC#)]
215-771-0 | [Molecular Formula]
C6H13NO5 | [MDL Number]
MFCD00082120 | [MOL File]
1404-88-2.mol | [Molecular Weight]
179.171 |
| Chemical Properties | Back Directory | [Definition]
An antibiotic produced by growth of Bacillus brevis. It consists of a mixture of antibiotics, principally gramicidin and tyrocidine. Gramicidin is the more active component. Use is generally limited to local external applications. It is active against some Gram-positive bacteria, including species of pneumococci, streptococci, and staphylococci.
| [Appearance]
White or almost white powder. | [storage temp. ]
Store at -20°C | [solubility ]
Practically insoluble in water, soluble in ethanol (96 per cent) and in methanol. | [form ]
neat | [color ]
White to off-white | [EPA Substance Registry System]
Tyrothricin (1404-88-2) |
| Hazard Information | Back Directory | [Brand name]
Bactratycin (Wallace). | [Chemical Properties]
White or almost white powder. | [Uses]
Tyrothricin is a complex of two unrelated peptide families, gramicidin complex and tyrocidines complex, produced by Bacillus brevis and discovered by Dubos in 1939. Typically, tyrothricin is composed of 20% of the linear pentadecylpeptide gramicidins and 80% of cyclic decapeptide tyrocidines. Both the gramicidins and tyrocidines act by disrupting bacterial cell wall integrity, but by differing mechanisms. Tyrothricin is used clinically for bacterial skin infections in some countries. | [in vivo]
In animal models using HSV type 1, a pre-incubation of the virus suspension with Tyrothricin could significantly decrease the lethality in mice. The effect could only be shown after a direct contact between Tyrothricin and the virus[1].
Nevertheless disruption of the integrity of eukaryotic membranes is observed at higher Tyrothricin concentrations in vitro. This effect is exemplified as hemolytic activity of Tyrothricin in in vitro studies and when applied to animals i.v.. In contrast to an intravenous (LD50 mouse: 3,7 mg/kg) and an intraperitoneal (LD50 mouse: 20-45 mg/kg) application the oral application is very well tolerated, as Tyrothricin is destroyed in the gastro-intestinal tract[1]. |
| Questions And Answer | Back Directory | [History]
At the Rockefeller Institute in New York in 1939, Rene Dubos isolated a bactericidal, proteinfree extract from Bacillus brevis.11 This material, tyrothricin, was soon shown to consist mainly of a cyclic decapeptide called tyrocidin, together with a similar compound called gramicidin S, which was 50 times as potent.12 Their structures were elucidated by Richard Synge at the Lister Institute in London using paper chromatography in one of its earliest applications.13,14 Although both components were able to protect mice against pneumococci, they were too toxic for general use.
 
Tyrothricin was suitable only for topical application. It was marketed in the USA by Sharp & Dohme in 1942 for treatment of Gram-positive infections. Since then, it has been universally used in throat lozenges as a non-prescription antibiotic, but the commercial success of this type of product has been largely due to the incorporation of benzocaine, a topical anaesthetic that soothes sore throats. |
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