106560-14-9

106560-14-9 structure

Name: Faropenem sodium hemipentahydrate
Chemical Name: 6α-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid
CAS Number: 106560-14-9
Molecular Formula: C₁₂H₁₅NO₅S
Molecular Weight: 285.316
Catalog: API Antibiotics Beta-lactamase inhibitor
Create Date: 2018-02-23 08:00:00
Modify Date: 2024-01-05 03:47:19
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].

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

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.

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

Risk Phrases	R20/21/22

1004548-62-2

106560-14-9

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

Precursor 1
1004548-62-2
DownStream 0

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