Panipenem Chemical Properties

Melting point:

198-200° (dec)

Boiling point:

555.5±60.0 °C(Predicted)

Density 

1.62±0.1 g/cm3(Predicted)

storage temp. 

Amber Vial, Hygroscopic, -20°C Freezer, Under inert atmosphere

solubility 

DMSO (Slightly), Methanol (Very Slightly), Water (Slightly)

pka

4.30±0.40(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic, Light Sensitive

CAS DataBase Reference

87726-17-8(CAS DataBase Reference)

Safety Information

Toxicity

Approx LD50 in male, female mice (mg/kg): 1700-2200, 1300-1700 i.v. (Kimura)

Panipenem Usage And Synthesis

Carbapenems

Panipenem is a carbapenem antibiotic,it is successfully developed by Japan Sankyo ,it has a broad antimicrobial spectrum , and it has strong antibacterial activity. This product is more stable, and its antibacterial spectrum is similar to imipenem ,it has a strong antibacterial effect on Gram-positive bacteria and negative bacteria, aerobic and anaerobic bacteria ,its effect on Staphylococcus aureus and methicillin-resistant Staphylococcus aureus is superior to that of imipenem, its effect on Escherichia coli, Klebsiella pneumoniae, Haemophilus influenzae, indole-positive and negative Proteus, Citrobacter, Serratia bacteria is stronger than imipenem, the effect on Pseudomonas aeruginosa is slightly lower than imipenem. To further enhance security, the antibiotic and kidney-protecting agent organic ion transport inhibitors Betamipron as 1:1 ratio are usd for the synthesis of compound preparation, Betamipron does not inhibit the dehydrogenation peptidase,it also has no inhibitory and other pharmacological effects, it only suppresses organic ion transport,it reduces kidney toxicity, it is clinically used for the treatment of bacteremia, sepsis, cholecystitis, liver abscess, peritonitis, inflammation of the eye, otitis media, endocarditis, skin and soft tissue infections, lower respiratory tract infections, genitourinary infections, gynecological infections caused by staphylococcus, streptococcus, enterococcus and other sensitive strains.

Three kinds of carbapenems contrast

Meropenem, imipenem and panipenem these three carbapenems all have good antibacterial activity on all kinds of G + and G-bacteria bacteria, aerobic and anaerobic bacteria ,they are clinically used for severe infections, mixed infections, nosocomial infections, and immunocompromised infection caused by production enzyme strains, and multi-drug resistant strains and G-mainly bacteria.
The differences between the three are as follows:
1, each has different focuses,their anaerobic antibacterial spectrums are similar ; for unfermentable negative bacteria of the aerobic , meropenem is the most active, followed by imipenem, panipenem. For G + bacteria, panipenem is the strongest.
2, imipenem has the highest incidence of adverse reactions on the central nervous system , meropenem and panipenem are lower.
3, imipenem is instable to human renal dehydropeptidase,it should to be added with the enzyme inhibitor cilastatin. And meropenem and panipenem are stable to human renal dehydropeptidase. Panipenem have some kidney toxicity, often plus betamethasone in order to reduce nephrotoxicity.
4, imipenem and panipenem are only available for intravenous, intramuscular meropenem can be used.
The above information is edited by the chemicalbook of Tian Ye.

Adverse reactions

Patients allergic to β-lactam antibiotics are banned.
The elderly, pregnant women, young children and kidney dysfunction patients should use with caution.
Diarrhea, belching, vomiting, rash.
Reduce the number of red blood cells and white blood cells, increase eosinophils.

Uses

Panipenem is a broad spectrum carbapenem antibacterial and antimicrobial agent working against Gram-negative and Gram-positive organisms.

Definition

ChEBI: Panipenem is an organic molecular entity.

Antimicrobial activity

A 3-acetimidoylpyrrolidinyl-substituted carbapenem with no methyl group at the C-1 position. It has broad-spectrum antibacterial activity against Gram-positive and Gramnegative organisms very similar to that of other carbapenems. Activity against Ps. aeruginosa is similar to that of imipenem. It is co-administered in a ratio of 1:1 with betamipron (N-benzoyl-β-alanine), a renal anion transport inhibitor that decreases nephrotoxicity. Panipenem is slightly more stable to hydrolysis by dehydropeptidase than imipenem, but not as stable as meropenem or biapenem. It is hydrolyzed by carbapenemases.
Mean maximum blood concentrations following intravenous infusion of 0.5 g and 0.75 g of each component were 37 and 61 mg/L for panipenem and 24 and 39 mg/L for betamipron. Following intravenous infusion in children (10 mg or 20 mg of each component per kg), the half-life of panipenem was about 1.2 h; that of betamipron about 0.9 h. Drug levels in the CSF were at least eight-fold lower than serum concentrations.
Side effects are similar to those reported for other carbapenems (incidence <10%) and are generally mild. Patients with a history of previous hypersensitivity reactions to penicillins, cephalosporins or other β-lactam antibiotics should be treated cautiously.
Clinical use in serious infections is similar to that of other carbapenems.

Panipenem(87726-17-8)Related Product Information

• Pefloxacin
• Faropenem sodium hemipentahydrate
• AMIKACIN
• Tacrolimus
• Omeprazole
• Imipenem
• 2-(METHYLSULFONYL)ETHANOL
• Pyrrolidine
• Polyvinylpyrrolidone
• N-Methyl-2-pyrrolidone
• D-Penicillamine
• N-Vinyl-2-pyrrolidone
• (AZETIDIN-3-YL)METHANOL
• Panipenem
• panipenem-betamipron