Meropenem
Meropenem
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Meropenem

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Catalog Number PR119478567
CAS 119478-56-7
Structure
Synonyms Merrem; Meronem
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;trihydrate
Molecular Weight 437.5
Molecular Formula C17H31N3O8S
InChI InChI=1S/C17H25N3O5S.3H2O/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);3*1H2/t7-,8-,9+,10+,11-,12-;;;/m1.../s1
InChI Key CTUAQTBUVLKNDJ-OBZXMJSBSA-N
Drug Categories Amides; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; beta-Lactams; Carbapenems; Drugs that are Mainly Renally Excreted; Heterocyclic Compounds, Fused-Ring; Lactams; Penem Antibacterial; Sulfur Compounds; Thienamycins
Drug Interactions Abacavir-Meropenem may decrease the excretion rate of Abacavir which could result in a higher serum level.
Aceclofenac-Aceclofenac may decrease the excretion rate of Meropenem which could result in a higher serum level.
Acemetacin-Acemetacin may decrease the excretion rate of Meropenem which could result in a higher serum level.
Acenocoumarol-The risk or severity of bleeding can be increased when Meropenem is combined with Acenocoumarol.
Acetaminophen-Acetaminophen may decrease the excretion rate of Meropenem which could result in a higher serum level.
EC Number 642-885-1
Isomeric 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.O.O.O
Packaging 5kg/tin x 1tin/carton
Standard CP/BP/USP/EP/IP/JP
Type Small Molecule
Pharmacology

Indications

Meropenem is approved for use as a monotherapy in the management of various infections, provided they are caused by susceptible strains of specific microorganisms. It is indicated for the treatment of complicated skin and skin structure infections associated with Staphylococcus aureus (both beta-lactamase-producing and non-beta-lactamase-producing methicillin-susceptible isolates), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, and Enterococcus faecalis (excluding vancomycin-resistant strains). Additionally, it is effective against infections caused by Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis, and Peptostreptococcus species. Meropenem is also indicated for the treatment of complicated appendicitis and peritonitis caused by organisms such as viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, Bacteroides thetaiotaomicron, and Peptostreptococcus species. Furthermore, it is utilized in the treatment of bacterial meningitis due to Streptococcus pneumoniae, Haemophilus influenzae (both beta-lactamase-producing and non-beta-lactamase-producing isolates), and Neisseria meningitidis.

Pharmacodynamics

Meropenem functions as a broad-spectrum carbapenem antibiotic with efficacy against both Gram-positive and Gram-negative bacteria. It exerts its antibacterial effects by efficiently penetrating bacterial cells and disrupting the synthesis of essential cell wall components. This disruption results in bacterial cell death, thereby eliminating the infection.

Metabolism

Meropenem is predominantly excreted unchanged from the body. It undergoes minimal metabolic transformation, producing a single metabolite that is microbiologically inactive. This characteristic facilitates its efficient elimination while maintaining its therapeutic effectiveness.

Mechanism of Action

Meropenem exhibits bactericidal properties by inhibiting cell wall synthesis. It efficiently penetrates the cell walls of both Gram-positive and Gram-negative bacteria, reaching critical penicillin-binding protein (PBP) targets. The drug demonstrates its strongest affinities for PBPs 2, 3, and 4 in Escherichia coli and Pseudomonas aeruginosa, as well as PBPs 1, 2, and 4 in Staphylococcus aureus.

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