Faropenem sodium hemipentahydrate

Modify Date: 2024-01-05 03:47:19

Faropenem sodium hemipentahydrate Structure
Faropenem sodium hemipentahydrate structure
Common Name Faropenem sodium hemipentahydrate
CAS Number 106560-14-9 Molecular Weight 285.316
Density 1.6±0.1 g/cm3 Boiling Point 570.2±50.0 °C at 760 mmHg
Molecular Formula C12H15NO5S Melting Point N/A
MSDS N/A Flash Point 298.7±30.1 °C

 Use of Faropenem sodium hemipentahydrate


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].

 Names

Name 6α-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid
Synonym More Synonyms

 Faropenem sodium hemipentahydrate 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
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

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Faropenem sodium hemipentahydrate Structure

Faropenem sodiu...

CAS#:106560-14-9

Literature: WO2008/12830 A1, ; Page/Page column 7-8 ;

 Precursor & DownStream

Precursor  1

DownStream  0

 Synonyms

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
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