Faropenem sodium Chemical Properties

Melting point:

>85°C (dec.)

alpha 

D22 +60° (c = 0.10)

storage temp. 

-20°C

solubility 

H2O: ≥20mg/mL

form 

powder

color 

white to light brown

optical activity

[α]/D +120 to +130°, c =1.0 in water

Water Solubility 

H2O: ≥20mg/mL

Stability:

Hygroscopic

InChI

InChI=1/C12H15NO5S.Na/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6;/h5-7,11,14H,2-4H2,1H3,(H,16,17);/q;+1/p-1/t5-,6-,7+,11-;/s3

InChIKey

ICSAXRANXQSPQP-WWTPKCCHNA-M

SMILES

N12C([C@]([H])([C@H](O)C)[C@@]1([H])SC([C@@H]1OCCC1)=C2C([O-])=O)=O.[Na+] |&1:2,4,7,11,r|

Safety Information

WGK Germany 

3

Faropenem sodium Usage And Synthesis

Chemical Properties

Pale Yellow Crystals

Uses

Faropenem is an orally active beta-lactam antibiotic belonging to the penem group.

General Description

Faropenem sodium hydrate belongs to the penem group of antibiotics prescribed for oral usage. Enterobacteriaceae bacterial infections with cephalosporin resistance are susceptible to faropenem. Faropenem could be an effective antibiotic to treat urinary tract infections caused by extended-spectrum beta-lactamases (ESBL) producing bacteria.

Biochem/physiol Actions

Faropenem sodium is an ultra-broad spectrum, β-lactamase resistant, β-lactam antibiotic active against both Gram-positive and Gram-negative bacteria.

Synthesis

At room temperature, 150 g of Intermediate II was mixed with 1110 mL of dichloromethane and stirred until completely dissolved, followed by the addition of 18 g of triphenylphosphine and an ethyl acetate solution of sodium caprylate (prepared from 92 g of sodium isooctanoate and 1110 mL of ethyl acetate) to give a pale yellow transparent liquid. After displacing the air in the reaction system with nitrogen for 5 minutes, 2.664 g of tetrakis(triphenylphosphine)palladium was added under nitrogen protection. After addition, the reaction temperature was maintained at 25~30°C and stirred continuously under nitrogen protection for 40 minutes. Upon completion of the reaction, 40 g of pure water was added to the reaction solution at room temperature, and crystallization was carried out at a controlled temperature of 20~30 °C for 2 h. The reaction was then cooled to -5~0 °C and stirring was continued for 2 h. The reaction mixture was separated by filtration. The reaction mixture was separated by filtration and the filter cake was washed with 200 mL x 3 of ethyl acetate. Finally, the filter cake was dried under vacuum at 35~40 °C to give 119 g of white powdery product in 73.3% molar yield.

References

[1] Organic Process Research and Development, 2010, vol. 14, # 4, p. 939 - 941
[2] Patent: CN107337684, 2017, A. Location in patent: Paragraph 0052; 0086-0094; 0110-0112
[3] Bioorganic and Medicinal Chemistry, 1997, vol. 5, # 7, p. 1389 - 1399

Faropenem sodium(122547-49-3)Related Product Information

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