Meropenem

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Meropenem
Category Antibiotics
Catalog number BBF-05838
CAS 96036-03-2
Molecular Weight 383.46
Molecular Formula C17H25N3O5S
Purity >98%

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Description

Meropenem, a carbapenem antibiotic with a broad spectrum of activity, can be administered intravenously and is used for severe bacterial infections caused by sensitive agents. Meropenem inhibits cell wall synthesis in Gram-positive and Gram-negative bacteria. Meropenem has obvious inhibitory effect on aerobes and anaerobes including Klebsiella, E. coli, Enterococcus, Clostridium sp..

Specification

Related CAS 119478-56-7 (trihydrate) 211238-34-5 (sodium salt) 1465916-43-1 (x-hydrate)
Synonyms ICI 194660; ICI-194660; ICI194660; SM-7338; SM 7338; SM7338; [4R-[3(3S*,5S*),4α,5β,6β(R*)]]-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; Mepem; Merrem; Merrem IV; Antibiotic SM 7338; 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-(((3S,5S)-5-((dimethylamino)carbonyl)-3-pyrrolidinyl)thio)-6-((1R)-1-hydroxyethyl)-4-methyl-7-oxo-, (4R,5S,6S)-
Storage Store at -20°C
IUPAC Name (4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Canonical SMILES CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O
InChI InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
InChI Key DMJNNHOOLUXYBV-PQTSNVLCSA-N

Properties

Appearance Crystalline Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 627.4±55.0°C (Predicted)
Flash Point 333.2°C
Density 1.42±0.1 g/cm3 (Predicted)
Solubility Soluble in DMSO, Ethanol, Water
LogP -0.04130

Reference Reading

1. New analyses of MIC90 data to aid antibacterial drug discovery
Matthew F. Brown,* Rishi R. Gupta,* Max Kuhn, Mark E. Flanagan and Mark Mitton-Fry. Med. Chem. Commun., 2011, 2, 735
There are a number of examples in the literature describing statistical analyses of MIC90 raw data (arithmetic mean, geometric mean, median, mode, etc.) to enable rank-ordering compounds with the use of the geometric mean being somewhat common. Therefore, we have also included the geometric mean in our analysis for comparison (Table 1). As was the case with the BMIC90 parameter, confidence intervals for the geometric mean values are also quite wide and not useful with regard to rank-ordering analogs. As alluded to above, antibacterial research teams often make decisions around compound progression based on MIC90 data. Rank-ordering this set of analogs based solely on the MIC90 data would provide the following: 2 = 3 > 1 = 4 = 5 > BAL30072 > Meropenem. By using the parameters described above, we can attempt to provide a greater degree of separation. Recall that the FDR values strongly suggest that MIC90 values for all compounds are statistically different with 1 and 4 being the exceptions. With this in mind, recognizing the ranking trends observed for the BMIC90, NPS and geometric mean values could lead to the following rank-order: 2 > 3 > 1≈4 > 5 > BAL30072 > Meropenem. Obviously, given the wide confidence intervals associated with the BMIC90 and geometric mean values, this ranking cannot be stated with 100% confidence. Drug research teams regularly make decisions with regard to compound advancement based on a variety of information (potency, pharmacokinetics, safety, stability, ease of synthesis, etc.). The methods described above were designed to illustrate potential trends in potency data for single experiments; there is an inherent risk that the analysis could occasionally mislead. That said, the reality of antibacterial drug research involves teams making decisions based on MIC90 data, and while the methods described herein do not enable decisions with 100% confidence, we are hopeful that they may lead to better informed, higher quality decisions.

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