| Identification | More | [Name]
(4R,5S,6S)-3-[[(3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid | [CAS]
119478-56-7 | [Synonyms]
MEROPENEM
MEROPENEM TRIHYDRATE
MEROPENEM TRIHYDROCHLORIDE
(4R,5S,6S)-3-[[(3S,5S)-5-(Dimethylcarbamoyl)-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid trihydrate
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, trihydrate, [4R-[3(3S*,5S*),4a,5b,6b(R*)]]-(9CI)
3-[[5-[(Dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylic acid trihydrate
(4R,5S,6S)-3-[[(3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Meropenem
MEROPENEMTRIHYDRATE(3-[[5-[(DIMETHYLAMINO)CARBONYL]-3-PYRROLIDINYL]THIO]-6-(1-HYDROXYETHYL)-4-METHYL-7-OXO-1-AZABICYCLO[3,2,0]HEPT-2-ENE-2-CARBOXYLICACIDTRIHYDRATE)
MEROPENEM WITH SODIUM CARBONATE | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C17H25N3O5S | [MDL Number]
MFCD00864966 | [Molecular Weight]
383.46 | [MOL File]
119478-56-7.mol |
| Questions And Answer | Back Directory | [Preparation]
Using protected meropenem as a starting material and water as the sole solvent, a deprotection reaction was carried out in the presence of an alkaline environment and a catalyst, employing a non-hydrogen reducing agent, to obtain the target product, meropenem trihydrate. |
| Chemical Properties | Back Directory | [Melting point ]
>192°C (dec.) | [alpha ]
-17～-21゜(d/20℃)(c=0.5,H2O)(calculated on the dehydrous basis) | [Boiling point ]
627℃ | [RTECS ]
CL5446509 | [Fp ]
>110°(230°F) | [storage temp. ]
-20°C | [solubility ]
Soluble in aqueous solution at approximately 5mg/ml | [form ]
powder | [color ]
white to off-white | [Merck ]
14,5900 | [InChIKey]
DMJNNHOOLUXYBV-PQTSNVLCSA-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)N(C)C)C1)(=O)O.O |&1:3,5,7,9,16,19,r| | [CAS DataBase Reference]
119478-56-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
White or slight-yellow crystalline powder LOD ≤0.5% Heavy Metals ≤20 ppm | [Uses]
Meropenem Trihydrate is a carbapenem antibiotic with wide spectrum of antibacterial. | [Application]
Meropenem trihydrate is a thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.
Meropenem trihydrate has also been used in the
antibiotic susceptibility testing of E coli isolates from harbor estuary sediment samples.
in the bacterial killing assay and for screening antibiotic resistance of cystic fibrosis patient′s sputum based Staphylococcus aureus transformed macrophages in phagocyte infection.
for screening Enterococcus faecalis from human bile. | [Definition]
ChEBI:Meropenem trihydrate is a hydrate. It has a role as an antibacterial drug. It contains a meropenem. | [Brand name]
Merrem I.V. (AstraZeneca). | [Antimicrobial activity]
The unique side chain at C-2 is associated with increased activity
against Gram-negative bacteria, including H. influenzae. It is
slightly less active than imipenem against Gram-positive organisms. It is active against anaerobes and more active
against some strains that are less susceptible to imipenem. Its
excellent activity against Gram-negative organisms is due to
high affinity for multiple penicillin-binding proteins (PBPs; see
p. 29). Activity is little affected by inoculum size or the presence
of serum. It is bactericidal at concentrations close to the MIC.
Stability to β-lactamases is similar to that of other
carbapenems: it is highly resistant to most serine
β-lactamases, including extended-spectrum enzymes, but
can be hydrolyzed by metallo-β-lactamases and by serine
carbapenemases. | [General Description]
Meropenem trihydrate (MRP) belongs to the carbapenem group of compounds. It is susceptible to degradation at high temperature and humidity. It is soluble in methanol-water or acetone-water combinations. It is used as an antibacterial agent for treating meningitis and pneumonia. | [Biological Activity]
meropenem trihydrate (sm-7338) is an active ingredient carbapenem antibiotic [1].meropenem trihydrate has shown the potent effect against gram-negative organisms with the mic90 values of 0.03μm, 0.06μm, 0.06μm, 0.12μm,0.25μm, 0.12μm, 0.06μm, 0.12μm and 0.25μm for escherichia coli (30), klebsiella pneumonia(29), klebsiella oxytoca (20), enterobacter aerogenes (14), enterobacter cloacae (29), citrobacter freundii (20), citrobacter diversus (12), proteus mirabilis (15) and morganella morganii (15), respectively. in addition, meropenem trihydrate has also been revealed to restrain gram-positive and anaerobic organisms with the mic90 values of 0.008μm, 4μm and 0.015μm for streptococcus pyogenes (20), viridans group streptococci (27), streptococcus pneumonia (15), respectively. furthermore, meropenem trihydrate has shown the different effect of ph on mic, for example, the mean mic values of 0.06μm and 0.03μm in ph5.5 and ph7.5, respectively [1]. | [Biochem/physiol Actions]
Meropenem trihydrate is an ultra-broad spectrum beta-lactam antibiotic active against both Gram-positive and Gram-negative bacteria. | [Pharmacokinetics]
Cmax 500 mg intravenous (30-min
infusion): 23 mg/L end infusion
1 g intravenous (30-min infusion): 49 mg/L end infusion
Plasma half-life: 1 h
Volume of distribution: c. 0.3 L/kg
Plasma protein binding: 2%
Absorption and distribution
Meropenem is not absorbed after oral administration. It
penetrates well into most body fluids and tissues, including
CSF, achieving concentrations matching or exceeding those
required to inhibit most susceptible bacteria. In pediatric
patients (1 month to 15 years) with inflamed meninges it
achieves CSF levels of 0.9–6.5 mg/L after a single intravenous
infusion (40 mg/kg) over 30 min. After a single intravenous
dose, the highest mean concentrations of meropenem were
found in tissues and fluids at 1 h (0.5–1.5 h) after the start
of infusion.
Metabolism and excretion
The mean recovery of unchanged meropenem is approximately
70%. The remainder consists of the microbiologically
inactive open-ring form. Renal excretion is greater than
70% of unchanged drug over 12 h. Co-administration with
probenecid prolongs the half-life 38%, but peak concentrations
are not greatly affected. In patients with renal impairment
the dose should be adjusted. Parent drug and metabolite
are removed by hemodialysis. | [Clinical Use]
Intra-abdominal infections
Bacterial meningitis (pediatric patients >3 months)
Complicated skin and skin structure infections | [Clinical Use]
Meropenem is a second-generation carbapenem that, todate, has undergone the most extensive clinical evaluation.It has recently been approved as Merrem for the treatmentof infections caused by multiply-resistant bacteria and forempirical therapy for serious infections, such as bacterialmeningitis, septicemia, pneumonia, and peritonitis.Meropenem exhibits greater potency against Gram-negativeand anaerobic bacteria than does imipenem, but it is slightlyless active against most Gram-positive species. It is not effectiveagainst MRSA. Meropenem is not hydrolyzed byDHP-I and is resistant to most β-lactamases, including a fewcarbapenemases that hydrolyze carbapenem.
Like imipenem, meropenem is not active orally. It is providedas a sterile lyophilized powder to be made up innormal saline or 5% dextrose solution for parenteral administration.Approximately 70% to 80% of unchangedmeropenem is excreted in the urine following intravenous orintramuscular administration. The remainder is the inactivemetabolite formed by hydrolytic cleavage of the β-lactamring. The lower incidence of nephrotoxicity of meropenem(compared with imipenem) has been correlated with itsgreater stability to DHP-I and the absence of the DHP-Iinhibitor cilastatin in the preparation. Meropenem appears to be less epileptogenic than imipenem when the two agentsare used in the treatment of bacterial meningitis. | [Indications]
Intra-abdominal infections
Bacterial meningitis (pediatric patients >3 months)
Complicated skin and skin structure infections | [Side effects]
Seizures and other CNS adverse experiences have been
reported in 0.7% of all adult patients, most commonly those
with pre-existing CNS disorders. Pseudomembranous colitis
has been reported. Other reactions include diarrhea (4.8%),
nausea and vomiting (3.6%), inflammation at the site of
injection (2.4%) and headache (2.3%). Moniliasis occurs in
1.9–3.1% of pediatric patients.
Patients with a history of hypersensitivity reactions to other
β-lactam agents should be treated cautiously. | [Drug interactions]
Potentially hazardous interactions with other drugs
Antiepileptics: concentration of valproate reduced -
avoid.
Probenecid: avoid concomitant use | [Metabolism]
Meropenem is more stable to renal dehydropeptidase I
than imipenem but undergoes some renal metabolism,
and is mainly excreted in the urine by tubular secretion
and glomerular filtration. About 70% of a dose is
recovered unchanged in the urine over a 12-hour period.
Meropenem is reported to have one metabolite (ICI 213689), which is inactive and is excreted in the urine. | [storage]
Store at -20°C | [References]
[1] neu hc1, novelli a, chin nx.in vitro activity and beta-lactamase stability of a new carbapenem, sm-7338.antimicrob agents chemother. 1989 jul; 33(7):1009-18. |
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