Tigemonam
Tigemonam Basic information
- Product Name:
- Tigemonam
- Synonyms:
-
- Tigemonam
- [[[(Z)-1-(2-Aminothiazol-4-yl)-2-[[(3S)-2,2-dimethyl-4-oxo-1-(sulfooxy)azetidin-3-yl]amino]-2-oxoethylidene]amino]oxy]acetic acid
- Antibiotic SQ-30213
- SQ-30213
- Sulfuric acid [(3S)-3-[[2-(2-aminothiazol-4-yl)-2-[(Z)-carboxymethyloxyimino]-1-oxyethyl]amino]-4,4-dimethyl-2-oxoazetidin-1-yl] ester
- Tigemom
- Acetic acid, 2-[[(Z)-[1-(2-amino-4-thiazolyl)-2-[[(3S)-2,2-dimethyl-4-oxo-1-(sulfooxy)-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-
- 2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(3S)-2,2-dimethyl-4-oxo-1-sulfooxyazetidin-3-yl]amino]-2-oxoethylidene]amino]oxyaceticaci
- CAS:
- 102507-71-1
- MF:
- C12H15N5O9S2
- MW:
- 437.41
- Mol File:
- 102507-71-1.mol
Tigemonam Chemical Properties
- Density
- 1.91±0.1 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- Soluble in DMSO
- pka
- -3?+-.0.18(Predicted)
Tigemonam Usage And Synthesis
Uses
Tigemonam is a monobactam, with potent activity against Gram-negative aerobic bacterial pathogens.
Definition
ChEBI: Tigemonam is a monobactam.
Clinical Use
Tigemonam is a newer monobactam that is orally active.It is highly resistant to β-lactamases. The antibacterialspectrum of activity resembles that of aztreonam. It is veryactive against the Enterobacteriaceae, including E. coli,Klebsiella, Proteus, Citrobacter, Serratia, and Enterobacterspp. It also exhibits good potency against H. influenzae andN. gonorrhoeae. Tigemonam is not particularly activeagainst Gram-positive or anaerobic bacteria and is inactiveagainst P. aeruginosa.
In contrast to the poor oral bioavailability of aztreonam,the oral absorption of tigemonam is excellent. Itcould become a valuable agent for the oral treatment ofurinary tract infections and other non–life-threatening infectionscaused by β-lactamase–producing Gram-negativebacteria.
in vivo
Tigemonam shows potent activities against Escherichia coli SC 8294, E. coli SC 12199, Salmonella schottmulleri SC 3850, Proteus mirabilis SC 9575, Providencia rettgeri SC 8217, Klebsiella pneumoniae SC 12216, Serratia marcescens SC 9782, Enterobacter cloacae SC 11078, Haemophilus influenzae SC 10556, with ED50 of 1.4 mg/kg, 1.5 mg/kg, 0.7 mg/kg, 0.3 mg/kg, 0.2 mg/kg, 0.9 mg/kg, 0.5 mg/kg, 3.9 mg/kg and 1.8 mg/kg in mice[2].
References
[1] Rylander M, et al. Comparative in-vitro activity of tigemonam, a new monobactam. J Antimicrob Chemother. 1988 Sep;22(3):307-13. DOI:10.1093/jac/22.3.307
[2] Clark JM, et al. In vivo evaluation of tigemonam, a novel oral monobactam. Antimicrob Agents Chemother. 1987 Feb;31(2):226-9. DOI:10.1128/AAC.31.2.226
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