| Identification | Back Directory | [Name]
Faropenem sodium | [CAS]
122547-49-3 | [Synonyms]
alp201
sy5555
ym-044
wy49605
sun5555
Furopenem
fropenumsodium
Sodium faropenem
Faropenem sodium
Suflopenem sodium
Faropenem sodium hydrate
FAROPENEM SODIUM SALT HEMIPENTAHYDRATE
o-3-(tetrahydro-2-furanyl)-,monosodiumsalt,(5r-(3(r*),5-alpha,6-alpha(r*)))
(5r,6s)-6-(1(r)-hydroxyethyl)-2-(2(r)-tetrahydrofuryl)penem-3-carboxylicacid
(5R,6S,8R,2′R)-2-(2′-tetrahydrofuryl)-6-hydroxyethylpenem-3-carboxylate sodium salt
(5R)-6β-[(R)-1-Hydroxyethyl]-3-[(2R)-oxolan-2-yl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt
sodiuM (5S,6R)-6-((S)-1-hydroxyethyl)-7-oxo-3-((R)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
(5R,6S)-6-[(R)-1-Hydroxyethyl]-7-oxo-3-[[(R)-tetrahydrofuran]-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt
4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-, monosodium salt, (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 monosodium salt hemipentahydrate
6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-,monosodiumsalt,(5r-(3(r*),5-alpha,6-alpha(r*)4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylicaci
4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, monosodium salt, [5R-[3(R*),5α,6α(R*)]]-
(5r-(3(r*),5-alpha,6-alpha(r*)))-6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-4-thia-1-azabicyclo(3.2.0) hept-2-ene-2-carboxylic acid monosodium salt
(5r-(3(r*),5-alpha,6-alpha(r*)))-6-(1-hydroxyethyl)-7-oxo-3- (tetrahydro-2-furanyl)-4-thia-1-azabicyclo(3.2.0) hept-2-ene-2-carboxylic acid monosodium salt | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C12H14NO5S.Na | [MDL Number]
MFCD07357271 | [MOL File]
122547-49-3.mol | [Molecular Weight]
307.3 |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Crystals | [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 Rotation]
[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| |
| Hazard Information | Back Directory | [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 |
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