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Identification
Name Meropenem
Accession Number DB00760 (APRD01097, EXPT02153)
Type small molecule
Groups approved
Description

Meropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Antibiotic SM 7338
  • meropenem
  • Meropenem anhydrous
  • Meropenemum [INN-Latin]
Brand names
  • Meronem
  • Merrem
  • Merrem I.V.
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Antibacterials for Systemic Use
CAS number 119478-56-7
Weight Average: 383.463
Monoisotopic: 383.151491615
Chemical Formula C17H25N3O5S
InChI Key InChIKey=DMJNNHOOLUXYBV-PQTSNVLCSA-N
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
Plain Text
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
SMILES
C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(S[C@@H]3CN[C@@H](C3)C(=O)N(C)C)=C(N2C1=O)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For use as single agent therapy for the treatment of the following infections when caused by susceptible isolates of the designated microorganisms: complicated skin and skin structure infections due to Staphylococcus aureus (b-lactamase and non-b-lactamase producing, methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (excluding vancomycin-resistant isolates), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis and Peptostreptococcus species; complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. Also for use in the treatment of bacterial meningitis caused by Streptococcus pneumoniae, Haemophilus influenzae (b-lactamase and non-b-lactamase-producing isolates), and Neisseria meningitidis.
Pharmacodynamics Meropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death.
Mechanism of action The bactericidal activity of meropenem results from the inhibition of cell wall synthesis. Meropenem readily penetrates the cell wall of most Gram-positive and Gram-negative bacteria to reach penicillin-binding- protein (PBP) targets. Its strongest affinities are toward PBPs 2, 3 and 4 of Escherichia coli and Pseudomonas aeruginosa; and PBPs 1, 2 and 4 of Staphylococcus aureus.
Absorption Not Available
Volume of distribution Not Available
Protein binding Approximately 2%.
Metabolism

Primarily excreted unchanged. There is one metabolite which is microbiologically inactive.
Route of elimination Approximately 70% of the intravenously administered dose is recovered as unchanged meropenem in the urine over 12 hours, after which little further urinary excretion is detectable.
Half life Approximately 1 hour in adults and children 2 years of age and older with normal renal function. Approximately 1.5 hours in children 3 months to 2 years of age.
Clearance Not Available
Toxicity In mice and rats, large intravenous doses of meropenem (2200-4000 mg/kg) have been associated with ataxia, dyspnea, convulsions, and mortalities.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • Astrazeneca uk ltd
Packagers
Dosage forms
Form Route Strength
Powder, for solution Intravenous
Prices
Unit description Cost Unit
Merrem 1 gm Solution Vial 81.32 USD vial
Merrem iv 1 gm vial 78.19 USD vial
Merrem 500 mg Solution Vial 48.79 USD vial
Patents
Country Patent Number Approved Expires
United States 4943569 1993-06-21 2010-06-21
Canada 1322371 1993-09-21 2010-09-21
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
water solubility Sparingly PhysProp
logP -0.6 PhysProp
Predicted Properties
Property Value Source
water solubility 5.63e+00 g/l ALOGPS
logP -0.69 ALOGPS
logP -4.353987286652533 ChemAxon Molconvert
logS -1.83 ALOGPS
pKa 14.999794011052362 ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 110.18 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 97.8862 ChemAxon Molconvert
polarizability 39.28805653294991 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D02222 Link_out
ChEBI 43968 Link_out
ChEMBL 43968 Link_out
Therapeutic Targets Database DAP000441 Link_out
PharmGKB PA450383 Link_out
HET MER Link_out
Drug Product Database 2218496 Link_out
RxList http://www.rxlist.com/cgi/generic2/meropen.htm Link_out
Drugs.com http://www.drugs.com/cdi/meropenem.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Meropenem Link_out
ATC Codes
  • J01DH02
AHFS Codes
  • 08:12.07.08
PDB Entries Not Available
FDA label show (276.3 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Penicillin-binding protein 4

Pharmacological action: yes
Actions: inhibitor

Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction

Organism class: bacterial
UniProt ID: P24228 Link_out
Gene: dacB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Kanazawa K, Nouda H, Sunagawa M: Structure-activity relationships of carbapenem compounds to anti-Haemophilus influenzae activity and affinity for penicillin-binding proteins. Effect of 1 beta-methyl group and C-2 side chain. J Antibiot (Tokyo). 1997 Feb;50(2):162-8. Pubmed
  4. Ubukata K, Shibasaki Y, Yamamoto K, Chiba N, Hasegawa K, Takeuchi Y, Sunakawa K, Inoue M, Konno M: Association of amino acid substitutions in penicillin-binding protein 3 with beta-lactam resistance in beta-lactamase-negative ampicillin-resistant Haemophilus influenzae. Antimicrob Agents Chemother. 2001 Jun;45(6):1693-9. Pubmed
Enzymes

1. Beta-lactamase PSE-2

Actions: substrate

Hydrolyzes both carbenicillin and oxacillin

UniProt ID: P14489 Link_out
Gene: bla
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Pryka RD, Haig GM: Meropenem: a new carbapenem antimicrobial. Ann Pharmacother. 1994 Sep;28(9):1045-54. Pubmed
  2. Bonfiglio G, Russo G, Nicoletti G: Recent developments in carbapenems. Expert Opin Investig Drugs. 2002 Apr;11(4):529-44. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on December 19, 2011 21:43

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.