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(-)-Indolmycin

CAS No.
21200-24-8
Chemical Name:
(-)-Indolmycin
Synonyms
Pa-155-A;indolomycin;(-)-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)-
CBNumber:
CB62347060
Molecular Formula:
C14H15N3O2
Molecular Weight:
257.29
MDL Number:
MFCD01747966
MOL File:
21200-24-8.mol
MSDS File:
SDS
Last updated:2023-05-21 10:59:17

(-)-Indolmycin Properties

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
FDA UNII ZMC93U2C8P

(-)-Indolmycin price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 15385 Indolmycin ≥99% 21200-24-8 1mg $384 2024-03-01 Buy
Cayman Chemical 15385 Indolmycin ≥99% 21200-24-8 5mg $1452 2024-03-01 Buy
TRC I708160 Indolmycin 21200-24-8 1mg $185 2021-12-16 Buy
ApexBio Technology C5289 Indolmycin 21200-24-8 5mg $1659 2021-12-16 Buy
AK Scientific 0341EM Indolmycin 21200-24-8 5mg $1715 2021-12-16 Buy
Product number Packaging Price Buy
15385 1mg $384 Buy
15385 5mg $1452 Buy
I708160 1mg $185 Buy
C5289 5mg $1659 Buy
0341EM 5mg $1715 Buy

(-)-Indolmycin Chemical Properties,Uses,Production

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.

Uses

Indolmycin is an antibiotic that inhibits bacterial tryptophanyl-tRNA synthetase.

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.

(-)-Indolmycin Preparation Products And Raw materials

Raw materials

Preparation Products

(-)-Indolmycin Suppliers

Global( 26)Suppliers
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(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 Pa-155-A (-)-INDOLMYCIN 4(5H)-Oxazolone, 5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-(methylamino)-, (5S)- indolomycin 21200-24-8