Meropenem trihydrate CAS NO.119478-56-7

(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 Basic information

Product 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
Synonyms: 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)
CAS: 119478-56-7
MF: C17H25N3O5S
MW: 383.46
Mol File: 119478-56-7.mol

Meropenem Trihydrate Chemical Properties
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
CAS DataBase Reference    119478-56-7(CAS DataBase Reference)
Safety Information
Hazard Codes     Xi
Risk Statements     36/37/38
Safety Statements     26
WGK Germany     3
HS Code     2941906000
MSDS Information
Meropenem Trihydrate Usage And Synthesis
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.
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.
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    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.
Clinical Use    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.