| Identification | More | [Name]
Panipenem | [CAS]
87726-17-8 | [Synonyms]
(5r,6s)-2-[1-acetamidoylpyrrolidin-3(s)-ylthio]-6-[1(r)-hydroxyethyl]-2-carbapenem-3-carboxylic acid
PANIPENEM
(5r-(3(s*),5-alpha,6-alpha(r*)))-inoethyl)-3-pyrrolidinyl)thio)-7-oxo
1-azabicyclo(3.2.0)hept-2-ene-2-carboxylicacid,6-(1-hydroxyethyl)-3-((1-(1-im
6-(1-hydroxyethyl)-2-(1-acetimidoylpyrrolidin-3-ylthio)-1-carbaren-2-em-3-ca
carbapenemrs-533
cs533
FAROPENEM, 90.0%
(5R,6S)-3-[[(3S)-1-(1-Iminoethyl)-3β-pyrrolidinyl]thio]-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
(5R,6S)-3-[[(3S)-1-(1-Iminoethyl)pyrrolidin-3β-yl]thio]-6β-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
(5R,6S)-3-[[(3S)-1-Acetimidoyl-3-pyrrolidinyl]thio]-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic acid
PAPM | [Molecular Formula]
C15H21N3O4S | [MDL Number]
MFCD00865098 | [Molecular Weight]
339.41 | [MOL File]
87726-17-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
198-200° (dec) | [storage temp. ]
Amber Vial, Hygroscopic, -20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly), Methanol (Very Slightly), Water (Slightly) | [form ]
Solid | [color ]
White to Off-White | [Stability:]
Hygroscopic, Light Sensitive | [CAS DataBase Reference]
87726-17-8(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [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. |
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