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Faropenem sodium hemipentahydrate

Names

[ CAS No. ]:
106560-14-9

[ Name ]:
Faropenem sodium hemipentahydrate

[Synonym ]:
Faropenemsodiumhemipentahydrate
6alpha-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid
(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
(+)-(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
(5R,6S)-6-[1(R)-hydroxyethyl]-2-[2(R)-tetrahydrofuryl]penem-3-carboxylic acid
(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-keto-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
(+)-(5R,6S)-6-((1R)-1-Hydroxyethyl)-7-oxo-3-((2R)-tetrahydro-2-furyl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid
6α-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid
Faropenem sodium hemipentahydrate
(5R,6S,8R,2'R)-2-(2'-tetrahydrofuryl)-6-(1-hydroxyethyl)-2-penem-3-carboxylic acid
FAROPENEM
4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-, (5R,6S)-
4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-,(5R,6S)
FROPENEM
faropenem free acid

Biological Activity

[Description]:

Faropenem is a potent and orally active beta-lactam antibiotic. Faropenem demonstrates broad-spectrum in vitro antimicrobial activity against many gram-positive and -negative aerobes and anaerobes. Faropenem is resistant to hydrolysis by nearly all beta-lactamases, including extended-spectrum beta-lactamases and AmpC beta-lactamases. Faropenem is developed as an oral prodrug, faropenem medoxomil, for the research of respiratory tract infections[1][2].

[Related Catalog]:

Research Areas >> Infection

[In Vitro]

Faropenem is not active against methicillin-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus faecium, Pseudomonas aeruginosa or Stenotrophomonas maltophilia[1]. Faropenem is against all isolates of B. anthracis. The MIC values ranged from ≤0.06 to >64 μg/liter, and the MIC90 value is 0.5 μg/ml. The MIC90 value for Faropenem is lower than that observed for other β-lactams, such as Meropenem, Amoxicillin-clavulanate, and Penicillin, for which the MIC90 values are 4 μg/ml, 4 μg/ml, and 8 μg/ml, respectively[2].

[In Vivo]

Faropenem ( i.p. at 24 h postchallenge at 4-, 6-, and 12-h intervals; 10, 20, 40, and 80 mg/kg/day; 14 days) demonstrates a high level of activity against B. anthracis in the murine post-exposure prophylaxis inhalation model[1].

[References]

[1]. Kristen N Schurek, et al. Faropenem: review of a new oral penem. Expert Rev Anti Infect Ther. 2007 Apr;5(2):185-98.

[2]. Stanley C Gill, et al. Pharmacokinetic-pharmacodynamic assessment of faropenem in a lethal murine Bacillus anthracis inhalation postexposure prophylaxis model. Antimicrob Agents Chemother. 2010 May;54(5):1678-83.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
570.2±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C12H15NO5S

[ Molecular Weight ]:
285.316

[ Flash Point ]:
298.7±30.1 °C

[ Exact Mass ]:
285.067108

[ PSA ]:
112.37000

[ LogP ]:
-0.45

[ Vapour Pressure ]:
0.0±3.6 mmHg at 25°C

[ Index of Refraction ]:
1.668

[ Storage condition ]:
2-8°C

Safety Information

[ Risk Phrases ]:
R20/21/22

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds