| Identification | Back Directory | [Name]
(-)-Indolmycin | [CAS]
21200-24-8 | [Synonyms]
Pa-155-A
(-)-INDOLMYCIN
(S)-5-[(1R)-1-(1H-Indol-3-yl)ethyl]-2-(methylamino)-4(5H)-oxazolone
[5S,(-)]-5-[(R)-1-(1H-Indol-3-yl)ethyl]-2-methylamino-2-oxazolin-4-one
4(5H)-Oxazolone, 5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-(methylamino)-, (5S)- | [Molecular Formula]
C14H15N3O2 | [MDL Number]
MFCD01747966 | [MOL File]
21200-24-8.mol | [Molecular Weight]
257.29 |
| Chemical Properties | Back Directory | [Melting point ]
209-210° | [alpha ]
D25 -214° (c = 2 in methanol) | [Boiling point ]
420.8±37.0 °C(Predicted) | [density ]
1.36±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C, protect from light | [solubility ]
Soluble in ethanol;methanol;DMSO;dimethyl formamide | [form ]
powder | [pka]
16.65±0.30(Predicted) | [color ]
white |
| Hazard Information | Back Directory | [Uses]
Indolmycin is a highly selective antibiotic which acts as a tryptophan anti-metabolite. Recent research has shown that indolmycin is active against Mycobacteria and H. pylori, and can stimulate transcription in Escherichia coli. | [Definition]
ChEBI: A member of the class of 1,3-oxazoles that is 1,3-oxazol-4(5H)-one which is substituted at the 2 and 5-pro-S positions by methylamino and [(1R)-1-(1H-indol-3-yl)ethyl] gro
ps, respectively. | [Biological Activity]
indolmycin is an antibiotic.tryptophanyl-trna synthetase (trprs) catalyzes activation of tryptophan through atp and transfer to trnatrp , leading to translation of the genetic code for tryptophan. | [in vitro]
indolmycin was found to ba a bacteriostatic that showed good activity against methicillin-resistant s. aureus, methicillin-susceptible staphylococcus aureus, and vancomycin-intermediate s. aureus, including strains resistant to mupirocin or fusidic acid. spontaneous indolmycin-resistant mutants was observed at a lower frequency than those selected by mupirocin or fusidic acid and exhibited no cross-resistance with the comparative drugs. high-level resistance of indolmycin at its mic of 128 mg/l that was associated with an h43n mutation in tryptophanyl-trna synthetase, the target enzyme of indolmycin, led to loss of bacterial fitness. however, the locus responsible for low-level indolmycin resistance (indolmycin mics 8-32 mg/l) was not identified [1]. | [in vivo]
animal study found that indolmycin could completely clear h. pylori in experimentally infected mongolian gerbils at a dose of 10 mg/kg. therefore, indolmycin could be regarded as a candidate for the treatment of h. pylori infection [2]. | [IC 50]
30 μm for prokaryotic tryptophanyl-trna synthetase | [References]
[1] hurdle jg, o'neill aj, chopra i. anti-staphylococcal activity of indolmycin, a potential topical agent for control of staphylococcal infections. j antimicrob chemother. 2004 aug;54(2):549-52. epub 2004 jul 8.
[2] vecchione jj, sello jk. a novel tryptophanyl-trna synthetase gene confers high-level resistance to indolmycin. antimicrob agents chemother 2009; 53: 3972-3980. |
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