Meropenem

Meropenem
Clinical data
Trade namesMerrem, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: B2
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability100%
Protein bindingApproximately 2%
Elimination half-life1 hour
ExcretionKidney
Identifiers
  • (4R,5S,6S)-3-(((3S,5S)-5-(Dimethylcarbamoyl)pyrrolidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.169.299 Edit this at Wikidata
Chemical and physical data
FormulaC17H25N3O5S
Molar mass383.46 g·mol−1
3D model (JSmol)
  • O=C3N2\C(=C(\S[C@H]1C[C@@H](C(=O)N(C)C)NC1)[C@H](C)[C@@H]2[C@H]3[C@H](O)C)C(=O)O
  • 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 checkY
  • Key:DMJNNHOOLUXYBV-PQTSNVLCSA-N checkY
  (verify)

Meropenem, sold under the brand name Merrem among others, is an intravenous carbapenem antibiotic used to treat a variety of bacterial infections.[3] Some of these include meningitis, intra-abdominal infection, pneumonia, sepsis, and anthrax.[3]

Common side effects include nausea, diarrhea, constipation, headache, rash, and pain at the site of injection.[3] Serious side effects include Clostridioides difficile infection, seizures, and allergic reactions including anaphylaxis.[3] Those who are allergic to other β-lactam antibiotics are more likely to be allergic to meropenem as well.[3] Use in pregnancy appears to be safe.[3] It is in the carbapenem family of medications.[3] Meropenem usually results in bacterial death through blocking their ability to make a cell wall.[3] It is resistant to breakdown by many kinds of β-lactamase enzymes, produced by bacteria.[4][5]

Meropenem was patented in 1983.[6] It was approved for medical use in the United States in 1996.[3] It is on the World Health Organization's List of Essential Medicines.[7][8] The World Health Organization classifies meropenem as critically important for human medicine.[9]

  1. ^ "MEROPENEM-AFT (AFT Pharmaceuticals Pty Ltd)". Archived from the original on September 15, 2024. Retrieved September 15, 2024.
  2. ^ "Regulatory Decision Summary for Meropenem for Injection USP and Sodium Chloride Injection USP". Drug and Health Products Portal. January 4, 2024. Archived from the original on September 7, 2024. Retrieved April 2, 2024.
  3. ^ a b c d e f g h i "Meropenem". The American Society of Health-System Pharmacists. Archived from the original on January 20, 2011. Retrieved December 8, 2017.
  4. ^ Cite error: The named reference pmid18713049 was invoked but never defined (see the help page).
  5. ^ Michelow IC, McCracken GH (2009). "Antibacterial Therapeutic Agents". Feigin and Cherry's Textbook of Pediatric Infectious Diseases. pp. 3178–3227. doi:10.1016/B978-1-4160-4044-6.50253-3. ISBN 978-1-4160-4044-6. As with other β-lactam antibiotics, meropenem is bactericidal against susceptible bacteria because it inhibits bacterial cell wall synthesis. The trans configuration of the hydroxyethyl side chain and hydrogen atoms protect the parent β-lactam structure from inactivation by the most common β-lactamases, including almost all Bush groups 1 and 2 (Amber classes A, C, and D) β-lactamase–producing organisms, including those that produce ESBLs (Citrobacter, Enterobacter, E. coli, Klebsiella spp., and P. mirabilis) or AmpC β-lactamases (Citrobacter, Enterobacter, Pseudomonas, and Serratia)
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 497. ISBN 978-3-527-60749-5. Archived from the original on February 27, 2024. Retrieved September 20, 2020.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  9. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 978-92-4-151552-8.