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tebipenem

Names

[ CAS No. ]:
161715-21-5

[ Name ]:
tebipenem

[Synonym ]:
(1R,5S,6S)-6-(1(R)-Hydroxyethyl)-1-methyl-2-(1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl)-1-carba-2-penem-3-carboxylic acid
UNII-Q2TWQ1I31U
(4R,5S,6S)-3-{[1-(4,5-Dihydro-1,3-thiazol-2-yl)-3-azetidinyl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
tebipenem
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-, (4R,5S,6S)-
1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid,3-((1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-,(4R,5S,6S)

Biological Activity

[Description]:

Tebipenem is an orally available carbapenem antibiotic, shows broad-spectrum activity against Gram-positive and -negative bacteria, except for Pseudomonas aeruginosa.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial
Research Areas >> Infection

[In Vitro]

Tebipenem exhibits slow tight-binding inhibition at low micromolar concentrations versus the chromogenic substrate nitrocefin, and apparent Km and kcat values of 0.8 μM and 0.03 min-1, respectively[1]. Tebipenem shows potent activity against B. pseudomallei, with MIC50 and MIC90 values of both 2 mg/L[2]. Tebipenem shows good activity against S. pneumoniae, with the MIC range of ≤0.25 μg/mL in all of the S. pneumoniae isolates[3].

[References]

[1]. Hazra S, et al. Tebipenem, a new carbapenem antibiotic, is a slow substrate that inhibits the β-lactamase from Mycobacterium tuberculosis. Biochemistry. 2014 Jun 10;53(22):3671-8.

[2]. Seenama C, et al. In vitro activity of tebipenem against Burkholderia pseudomallei. Int J Antimicrob Agents. 2013 Oct;42(4):375.

[3]. Li H, et al. In vitro antibacterial activities of two novel oral antibiotics, tebipenem and cefditoren, and other comparators against community-acquired respiratory tract infection-associated bacterial pathogens: A multicentre study in China. Int J Antimicrob Agents. 2014 Jan;43(1):92-3.


[Related Small Molecules]

Puromycin 2HCl | Geneticin | Tunicamycin | Hygromycin B | Salinomycin | Avibactam sodium | Neomycin sulfate | Vaborbactam | Methicillin SodiuM | Rifampicin | Metronidazole | Carbenicillin disodium | Ceftazidime | Eravacycline dihydrochloride | cefotaxime sodium

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
624.5±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C16H21N3O4S2

[ Molecular Weight ]:
383.486

[ Flash Point ]:
331.5±34.3 °C

[ Exact Mass ]:
383.097351

[ PSA ]:
144.04000

[ LogP ]:
-1.71

[ Vapour Pressure ]:
0.0±4.1 mmHg at 25°C

[ Index of Refraction ]:
1.826

[ Storage condition ]:
2-8℃

Related Compounds