Ertapenem sodium Chemical Properties

Melting point:

>174oC (dec.)

storage temp. 

-70°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)

form 

powder

color 

white to beige

Water Solubility 

Fully miscible in water. Soluble in DMSO.

Stability:

Hygroscopic, Temperature Sensitive

InChIKey

FYIATPOZJSVTLD-KBQNSVMINA-N

SMILES

C(C1=C([C@H](C)[C@]2([H])[C@@]([H])([C@H](O)C)C(=O)N12)S[C@@H]1CN[C@H](C(=O)NC2C=CC=C(C(=O)O)C=2)C1)(=O)O.[NaH] |&1:3,5,7,9,16,19,r|

Ertapenem sodium Usage And Synthesis

Uses

Ertapenem sodium has been used as a carbapenem in the NitroSpeed-Carba NP test in minimum inhibitory concentration (MIC) testing for differentiation of carbapenemases in Enterobacterales and Pseudomonas aeruginosa. It has also been used as an antibiotic to study its effects on the survival of septic mice.

Definition

ChEBI: The monosodium salt of ertapenem. It is used for the treatment of moderate to severe susceptible infections including intra-abdominal and acute gynaecological infections, pneumonia, and infections of the skin and of the urinary tract. It is more stable to renal dehydropeptidase I tham imipenem, and so unlike imipenem, its use with cilastatin, which inhibits the enzyme, is not required.

Biochem/physiol Actions

Ertapenem is a broad spectrum carbopenem antibiotic. Ertapenem is active against both gram-positive and gram-negative bacteria. Ertapenem shows an extended duration of action in vivo due to its reversible binding to serum protein.

Synthesis

Synthesis of (4R,5S,6S)-3-(((3S,5S)-5-((3-carboxyphenyl)carbamoyl)pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(R)), according to the methodology described in CN102731508A, based on the compound (CAS: 202467-70-7) The general procedure for the monosodium salt of [3.2.0]hept-2-ene-2-carboxylic acid was as follows: to a solvent mixture of 750 mL of ethyl acetate and 500 mL of water was added the doubly protected crystalline form of Ertapenem (10 g, 0.017 mol) prepared in Example 1. The pH was adjusted to 7.1-7.2 with 5% aqueous sodium hydroxide, followed by the addition of 15 g of palladium carbon catalyst. The hydrogenation reaction was carried out under hydrogen pressure of 20.0-30.0 MPa for 2 hours. After completion of the reaction, the catalyst was removed by filtration and the filtrate was extracted with dichloromethane (100 mL x 2) to separate the aqueous layer. The aqueous layer was adsorbed through a macroporous adsorbent resin, followed by washing the resin with 2 L of deionized water. Next, the resin was eluted with acetone solution containing 0.05 M sodium bicarbonate, and after the eluate was acidified to pH 5.5, it was concentrated by nanofiltration to 50 mL. 100 g of a solvent mixture of methanol and n-propanol (W/W = 1:1) was added to the concentrated solution, and it was further concentrated to promote crystallization. The temperature of the crystallization process was controlled at 10-20 °C, and the product was collected by filtration upon completion of crystallization. The product was dried under vacuum at <0.09 MPa for 3 h. The final product was 3.4 g of Ertapenem monosodium salt in 40.2% yield and 99.2% purity by HPLC.

in vivo

IC 50

β-lactam

References

[1] Patent: CN104788452, 2017, B. Location in patent: Paragraph 0067; 0068
[2] Patent: WO2013/121279, 2013, A2. Location in patent: Page/Page column 15

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