Structure via PubChem · Public domain (PubChem)
meropenem
Sign in to saveAlso known as ICI-194660, SM-7338, Merrem iv, Merrem, Antibiotic sm 7338, Meropenem trihydrate, (1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid, Meropenem anhydrous
Meropenem, sold under the brand name Merrem among others, is an intravenous carbapenem antibiotic used to treat a variety of bacterial infections. Some of these include meningitis, intra-abdominal infection, pneumonia, sepsis, and anthrax.
Chemical data
- Formula
- C17H25N3O5S
- Molecular weight
- 383.5 g/mol
- IUPAC name
- (4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-1-ium-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
- SMILES
- C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H]([NH2+]C3)C(=O)N(C)C)C(=O)[O-])[C@@H](C)O
- InChIKey
- DMJNNHOOLUXYBV-PQTSNVLCSA-N
- XLogP
- -1.7
- Polar surface area
- 143 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
13,589 papers- Meropenem use and therapeutic drug monitoring in clinical practice: a literature review.Journal of clinical pharmacy and therapeutics · 2021
- Meropenem clinical pharmacokinetics.Clinical pharmacokinetics · 1995
- Meropenem/Vaborbactam, the First Carbapenem/β-Lactamase Inhibitor Combination.The Annals of pharmacotherapy · 2018
- Ertapenem Versus Meropenem for the Treatment of Extended Spectrum Beta-Lactamase-Producing Enterobacterales Bacteremia in Critically Ill Patients.The Annals of pharmacotherapy · 2024
- Meropenem/Vaborbactam: A Review in Complicated Urinary Tract Infections.Drugs · 2018
via PubMed
Wikidata facts
- Mass
- 383.151
Show 6 more facts
- chemical formula
- C₁₇H₂₅N₃O₅S
- Commons category
- Meropenem
- 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
- canonical SMILES
- CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O
- World Health Organisation international non-proprietary name
- meropenem
- defined daily dose
- 2
Sources (7)
via Wikidata · CC0
~13 min read
Article
11 sectionsContents
- Medical uses
- Administration
- Side effects
- Interactions
- Pharmacology
- Mechanism of action
- Protein binding
- Research directions
- Society and culture
- Trade names
- References
Meropenem, sold under the brand name Merrem among others, is an intravenous carbapenem antibiotic used to treat a variety of bacterial infections. Some of these include meningitis, intra-abdominal infection, pneumonia, sepsis, and anthrax.
Common side effects include nausea, diarrhea, constipation, headache, rash, and pain at the site of injection. Serious side effects include Clostridioides difficile infection, seizures, and allergic reactions including anaphylaxis. Those who are allergic to other β-lactam antibiotics are more likely to be allergic to meropenem as well. Use in pregnancy appears to be safe. It is in the carbapenem family of medications. Meropenem usually results in bacterial death through blocking their ability to make a cell wall. It is resistant to breakdown by many kinds of β-lactamase enzymes, produced by bacteria to protect themselves from antibiotics.