Meropenem An antibiotic that has a high affinity for cell wall-synthesizing enzymes

Meropenem (CAS 96036-03-2)

Meropenem | CAS 96036-03-2 is rated 5.0 out of 5 by 1.
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Synonym: Meropenemum; Mesalazine; Mesalamine
Application: An antibiotic that has a high affinity for cell wall-synthesizing enzymes
CAS Number: 96036-03-2
Purity: ≥99%
Molecular Weight: 383.46
Molecular Formula: C17H25N3O5S
* Refer to Certificate of Analysis for lot specific data (including water content).
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Meropenem is a β-lactam antibiotic of the carbapenem subclass that has been shown to inhibit penicillinase-negative, -positive and methicillin-susceptible staphylococci. This compound demonstrates the ability to also affect strains of 11 species of streptococci. Mechanistic studies suggest that Meropenem's antimicrobial activity is based on its high affinity for the majority of penicillin-binding proteins, which are cell wall-synthesizing enzymes. Meropenem is very effective because it resists inactivation by the majority of microbial LACTB (β-lactamases) as well as kidney dehydropeptidase I. Experiments have shown Meropenem to have a low toxicity profile and, in contrast to similar compounds, no central nervous system toxicity.


References

1. Kayser, F H., et al., 1989. Activity of meropenem, against gram-positive bacteria. The Journal of antimicrobial chemotherapy. 24 Suppl A(): 101-12. PMID: 2808202
2. Honorato, J., et al., 1997. [Clinical pharmacology and indications of meropenem in severe pediatric infection]. Enfermedades infecciosas y microbiología clínica. 15 Suppl 1(): 38-44. PMID: 9410068
3. Cottagnoud, P., et al., 2002. Cellular and molecular aspects of drugs of the future: meropenem. Cellular and molecular life sciences : CMLS. 59(11): 1928-33. PMID: 12530523
4. Nicolau, David P., et al., 2008. Pharmacokinetic and pharmacodynamic properties of meropenem. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America. 47 Suppl 1(): S32-40. PMID: 18713048

Appearance :
Crystalline powder
Physical State :
Solid
Solubility :
Soluble in water (8 mg/ml at 25° C), 5% monobasic potassium phosphate solution, ethanol (<1 mg/ml at 25° C), and DMSO (77 mg/ml at 25° C).
Storage :
Store at 4° C
Melting Point :
325.85° C (Predicted)
Boiling Point :
~627.4° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.64 (Predicted)
Optical Activity :
α20/D -19°±2°, c = 0.44 in water
IC50 :
Displacement of [14C]benzylpenicillin : IC50 = 3.3 ng/ml (Pseudomonas aeruginosa ATCC 15692); Binding of bocillin FL to PBP4 : IC50 = 8 ng/ml (Pseudomonas aeruginosa PAO1 membranes); Binding of bocillin FL to PBP2 : IC50 = 8 ng/ml (Escherichia coli MC4100 membranes)
pK Values :
pKa: 4.27 (Predicted), pKb: 8.31 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
441130
Merck Index :
14: 5900
MDL Number :
MFCD00864966
Beilstein Registry :
6826115
SMILES :
C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O

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Certificate of Analysis

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Meropenem  Product Citations

See how others have used Meropenem. Click on the entry to view the PubMed entry .

Citations 1 to 1 of 1 total

PMID: # 27873658  Wong, MH. et al. 2015. J Glob Antimicrob Resist. 3: 109-114.

Citations 1 to 1 of 1 total

What is the water content of the compound?

Asked by: two2igm05
Thank you for your question. The water content for sc-205746 is 12.59%. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-11

What is the physical appearance of this compound?

Asked by: two2igm05
Thank you for your question. Meropenem, sc-205746, is a light yellow crystalline powder.
Answered by: TechService7
Date published: 2016-12-28

What is the potency of meropenem

Asked by: elif07
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Rated 5 out of 5 by from Sueke Sueke, H. et al. (PubMed 26325409) investigated the pharmacokinetics of Meropenem for sse in bacterial keratitis. Found that Meropenem has very low toxicity in vitro. It has good corneal penetration, achieving anterior chamber concentrations above MIC90 for bacteria such as Staphylococcus aureus, Pseudomonas aeruginosa, streptococci, coagulase-negative staphylococci, and the Enterobacteriaceae. -SCBT Publication Review
Date published: 2015-01-18
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