Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H25N3O5S.CO3.2Na |
| Molecular Weight | 489.451 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].[O-]C([O-])=O.[H][C@]12[C@@H](C)C(S[C@@H]3CN[C@@H](C3)C(=O)N(C)C)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O
InChI
InChIKey=SGVRKQURIVADFJ-OBZXMJSBSA-L
InChI=1S/C17H25N3O5S.CH2O3.2Na/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;2-1(3)4;;/h7-12,18,21H,5-6H2,1-4H3,(H,24,25);(H2,2,3,4);;/q;;2*+1/p-2/t7-,8-,9+,10+,11-,12-;;;/m1.../s1
DescriptionSources: https://web.archive.org/web/20161209014344/http://www.ds-pharma.com:80/rd/new_value/meropen.htmlCurator's Comment: description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050706s036lbl.pdf |
Sources: https://web.archive.org/web/20161209014344/http://www.ds-pharma.com:80/rd/new_value/meropen.html
Curator's Comment: description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050706s036lbl.pdf |
Meropenem (generic name: meropenem hydrate) is a carbapenem antibiotic for injection showing a strong antibacterial activity to a wide range of bacteria strains from Gram-positive bacteria, Gram-negative bacteria to anaerobic bacteria. It is used as single agent therapy for the treatment of the following infections: 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. This drug also used in case of Intra-abdominal Infections for the treatment complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. In addition is used the treatment of bacterial meningitis caused by Streptococcus pneumoniae, Haemophilus influenzae (b-lactamase and non-b-lactamase-producing isolates), and Neisseria meningitides. 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. Meropenem has significant stability to hydrolysis by β-lactamases, both penicillinases and cephalosporinases produced by Gram-positive and Gram-negative bacteria. Meropenem should not be used to treat methicillin-resistant Staphylococcus aureus (MRSA) or methicillin-resistant Staphylococcus epidermidis (MRSE). Meropenem product with such superior effectiveness and safety has been approved for marketing by 100 countries or more in the world (as of March 2004) since its first launch in Italy in 1994.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2354204 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | MERREM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Meropenem for injection, USP (I.V.) and other antibacterial drugs, Meropenem for injection, USP (I.V.) should only be used to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Meropenem for injection, USP (I.V.) is useful as presumptive therapy in the indicated condition (e.g. intra-abdominal infections) prior to the identification of the causative organisms because of its broad spectrum of bactericidal activity. For information regarding use in pediatric patients see Indications and Usage (1.1), (1.2) or (1.3); Dosage and Administration (2.3), Adverse Reactions (6.1), and Clinical Pharmacology (12.3). Meropenem for injection (I.V.) is a penem antibacterial indicated as single agent therapy for the treatment of: Complicated skin and skin structure infections (adult patients and pediatric patients 3 months of age and older only). (1.1) Complicated intra-abdominal infections (adult and pediatric patients). (1.2) Bacterial meningitis (pediatric patients 3 months of age and older only). (1.3) To reduce the development of drug-resistant bacteria and maintain the effectiveness of Meropenem for injection (I.V.) and other antibacterial drugs, Meropenem for injection (I.V.) should only be used to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. 1.1 Skin and Skin Structure Infections (Adult Patients and Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated skin and skin structure infections due to Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (vancomycin-susceptible isolates only), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis, and Peptostreptococcus species. 1.2 Intra-abdominal Infections (Adult and Pediatric Patients) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. 1.3 Bacterial Meningitis (Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of bacterial meningitis caused by Streptococcus pneumoniae ‡, Haemophilus influenzae, and Neisseria meningitidis. ‡ The efficacy of meropenem as monotherapy in the treatment of meningitis caused by penicillin nonsusceptible isolates of Streptococcus pneumoniae has not been established. Meropenem for injection, USP (I.V.) has been found to be effective in eliminating concurrent bacteremia in association with bacterial meningitis., 1.1 Skin and Skin Structure Infections (Adult Patients and Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated skin and skin structure infections due to Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (vancomycin-susceptible isolates only), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis, and Peptostreptococcus species., 1.2 Intra-abdominal Infections (Adult and Pediatric Patients) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species., 1.3 Bacterial Meningitis (Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of bacterial meningitis caused by Streptococcus pneumoniae ‡, Haemophilus influenzae, and Neisseria meningitidis. ‡ The efficacy of meropenem as monotherapy in the treatment of meningitis caused by penicillin nonsusceptible isolates of Streptococcus pneumoniae has not been established. Meropenem for injection, USP (I.V.) has been found to be effective in eliminating concurrent bacteremia in association with bacterial meningitis. Launch Date1996 |
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| Primary | MERREM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Meropenem for injection, USP (I.V.) and other antibacterial drugs, Meropenem for injection, USP (I.V.) should only be used to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Meropenem for injection, USP (I.V.) is useful as presumptive therapy in the indicated condition (e.g. intra-abdominal infections) prior to the identification of the causative organisms because of its broad spectrum of bactericidal activity. For information regarding use in pediatric patients see Indications and Usage (1.1), (1.2) or (1.3); Dosage and Administration (2.3), Adverse Reactions (6.1), and Clinical Pharmacology (12.3). Meropenem for injection (I.V.) is a penem antibacterial indicated as single agent therapy for the treatment of: Complicated skin and skin structure infections (adult patients and pediatric patients 3 months of age and older only). (1.1) Complicated intra-abdominal infections (adult and pediatric patients). (1.2) Bacterial meningitis (pediatric patients 3 months of age and older only). (1.3) To reduce the development of drug-resistant bacteria and maintain the effectiveness of Meropenem for injection (I.V.) and other antibacterial drugs, Meropenem for injection (I.V.) should only be used to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. 1.1 Skin and Skin Structure Infections (Adult Patients and Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated skin and skin structure infections due to Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (vancomycin-susceptible isolates only), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis, and Peptostreptococcus species. 1.2 Intra-abdominal Infections (Adult and Pediatric Patients) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. 1.3 Bacterial Meningitis (Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of bacterial meningitis caused by Streptococcus pneumoniae ‡, Haemophilus influenzae, and Neisseria meningitidis. ‡ The efficacy of meropenem as monotherapy in the treatment of meningitis caused by penicillin nonsusceptible isolates of Streptococcus pneumoniae has not been established. Meropenem for injection, USP (I.V.) has been found to be effective in eliminating concurrent bacteremia in association with bacterial meningitis., 1.1 Skin and Skin Structure Infections (Adult Patients and Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated skin and skin structure infections due to Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (vancomycin-susceptible isolates only), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis, and Peptostreptococcus species., 1.2 Intra-abdominal Infections (Adult and Pediatric Patients) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species., 1.3 Bacterial Meningitis (Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of bacterial meningitis caused by Streptococcus pneumoniae ‡, Haemophilus influenzae, and Neisseria meningitidis. ‡ The efficacy of meropenem as monotherapy in the treatment of meningitis caused by penicillin nonsusceptible isolates of Streptococcus pneumoniae has not been established. Meropenem for injection, USP (I.V.) has been found to be effective in eliminating concurrent bacteremia in association with bacterial meningitis. Launch Date1996 |
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| Curative | MERREM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Meropenem for injection, USP (I.V.) and other antibacterial drugs, Meropenem for injection, USP (I.V.) should only be used to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Meropenem for injection, USP (I.V.) is useful as presumptive therapy in the indicated condition (e.g. intra-abdominal infections) prior to the identification of the causative organisms because of its broad spectrum of bactericidal activity. For information regarding use in pediatric patients see Indications and Usage (1.1), (1.2) or (1.3); Dosage and Administration (2.3), Adverse Reactions (6.1), and Clinical Pharmacology (12.3). Meropenem for injection (I.V.) is a penem antibacterial indicated as single agent therapy for the treatment of: Complicated skin and skin structure infections (adult patients and pediatric patients 3 months of age and older only). (1.1) Complicated intra-abdominal infections (adult and pediatric patients). (1.2) Bacterial meningitis (pediatric patients 3 months of age and older only). (1.3) To reduce the development of drug-resistant bacteria and maintain the effectiveness of Meropenem for injection (I.V.) and other antibacterial drugs, Meropenem for injection (I.V.) should only be used to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. 1.1 Skin and Skin Structure Infections (Adult Patients and Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated skin and skin structure infections due to Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (vancomycin-susceptible isolates only), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis, and Peptostreptococcus species. 1.2 Intra-abdominal Infections (Adult and Pediatric Patients) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. 1.3 Bacterial Meningitis (Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of bacterial meningitis caused by Streptococcus pneumoniae ‡, Haemophilus influenzae, and Neisseria meningitidis. ‡ The efficacy of meropenem as monotherapy in the treatment of meningitis caused by penicillin nonsusceptible isolates of Streptococcus pneumoniae has not been established. Meropenem for injection, USP (I.V.) has been found to be effective in eliminating concurrent bacteremia in association with bacterial meningitis., 1.1 Skin and Skin Structure Infections (Adult Patients and Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated skin and skin structure infections due to Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (vancomycin-susceptible isolates only), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis, and Peptostreptococcus species., 1.2 Intra-abdominal Infections (Adult and Pediatric Patients) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species., 1.3 Bacterial Meningitis (Pediatric Patients 3 Months of age and older only) Meropenem for injection, USP (I.V.) is indicated as a single agent therapy for the treatment of bacterial meningitis caused by Streptococcus pneumoniae ‡, Haemophilus influenzae, and Neisseria meningitidis. ‡ The efficacy of meropenem as monotherapy in the treatment of meningitis caused by penicillin nonsusceptible isolates of Streptococcus pneumoniae has not been established. Meropenem for injection, USP (I.V.) has been found to be effective in eliminating concurrent bacteremia in association with bacterial meningitis. Launch Date1996 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Safety profile of meropenem: a review of nearly 5,000 patients treated with meropenem. | 1999 |
|
| Investigation of synergism of meropenem and ciprofloxacin against Pseudomonas aeruginosa and Acinetobacter strains isolated from intensive care unit infections. | 2001 |
|
| [Antibiotic therapy of cystic fibrosis in children]. | 2001 |
|
| [Antimicrobial activities of meropenem against clinically isolated strains in 1999]. | 2001 Apr |
|
| Monotherapy with meropenem versus combination therapy with piperacillin plus amikacin as empiric therapy for neutropenic fever in children with lymphoma and solid tumors. | 2001 Apr-Jun |
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| [Antimicrobial activities and mechanisms of carbapenem resistance in clinical isolates of carbapenem-resistant Pseudomonas aeruginosa and Acinetobacter spp]. | 2001 Aug |
|
| In vitro activity of fosfomycin in combination with various antistaphylococcal substances. | 2001 Aug |
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| Antimicrobial susceptibility of respiratory isolates of Enterobacteriaceae and Staphylococcus aureus in Italy: incidence and trends over the period 1997-1999. | 2001 Dec |
|
| MYSTIC program: summary of European data from 1997 to 2000. | 2001 Dec |
|
| MYSTIC (Meropenem Yearly Susceptibility Test Information Collection) conference. Hamburg, Germany, 10 May 2001. | 2001 Dec |
|
| A novel metallo-beta-lactamase, Mbl1b, produced by the environmental bacterium Caulobacter crescentus. | 2001 Dec 14 |
|
| [Microbiological monitoring of the microbic strain stability to antibacterial preparations in surgical in-patient clinics]. | 2001 Feb |
|
| Carbapenem-resistant Serratia marcescens isolates producing Bush group 2f beta-lactamase (SME-1) in the United States: results from the MYSTIC Programme. | 2001 Feb |
|
| Properties of multidrug-resistant, ESBL-producing Proteus mirabilis isolates and possible role of beta-lactam/beta-lactamase inhibitor combinations. | 2001 Feb |
|
| [Clinical effects of meropenem on infectious diseases in obstetrics and gynecology]. | 2001 Jan |
|
| Meropenem in neonatal severe infections due to multiresistant gram-negative bacteria. | 2001 Jan |
|
| Nosocomial pneumonia. Diagnostic and therapeutic considerations. | 2001 Jan |
|
| [Prevalence of Moraxella catarrhalis colonization in asymptomatic carriers under 6 years of age]. | 2001 Jan-Feb |
|
| [In vitro and in vivo activities of panipenem against penicillin-resistant Streptococcus pneumoniae]. | 2001 Jul |
|
| Antibiotic therapy in intra-abdominal infections--a review on randomised clinical trials. | 2001 Jul 30 |
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| Treatment of nosocomial pneumonia: an experience with meropenem. | 2001 Jun |
|
| Antimicrobial susceptibility of Pseudomonas aeruginosa: results of a UK survey and evaluation of the British Society for Antimicrobial Chemotherapy disc susceptibility test. | 2001 Jun |
|
| Pharmacokinetics of meropenem in preterm neonates. | 2001 Jun |
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| Antifungal antibiotics and breakthrough bacteremias. | 2001 Jun 1 |
|
| In vitro activity of mezlocillin, meropenem, aztreonam, vancomycin, teicoplanin, ribostamycin and fusidic acid against Borrelia burgdorferi. | 2001 Mar |
|
| Adult Enterobacter meningitis: a high incidence of coinfection with other pathogens and frequent association with neurosurgical procedures. | 2001 Mar-Apr |
|
| [Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (1999). I. Susceptibility distribution]. | 2001 May |
|
| Antibiotic selective pressure and development of bacterial resistance. | 2001 May |
|
| Epidemiologic Study of Pseudomonas aeruginosa in critical patients and reservoirs. | 2001 May-Jun |
|
| Influence of in-vivo endotoxin liberation on anti-anaerobic antimicrobial efficacy. | 2001 Oct |
|
| Frequency of isolation and antimicrobial resistance of gram-negative and gram-positive bacteria from patients in intensive care units of 25 European university hospitals participating in the European arm of the SENTRY Antimicrobial Surveillance Program 1997-1998. | 2001 Sep |
|
| Isolation and culture of airway epithelial cells from chronically infected human lungs. | 2001 Sep |
|
| Characterization of paired mucoid/non-mucoid Pseudomonas aeruginosa isolates from Danish cystic fibrosis patients: antibiotic resistance, beta-lactamase activity and RiboPrinting. | 2001 Sep |
|
| Carbapenem-resistant Acinetobacter and role of curtains in an outbreak in intensive care units. | 2002 Feb |
|
| Acute necrotizing gastritis by Escherichia coli in a severely neutropenic patient. | 2002 Jan |
|
| Primary liver abscess caused by one clone of Klebsiella pneumoniae with two colonial morphotypes and resistotypes. | 2002 Jan |
Sample Use Guides
Adult Patients: The recommended dose of MERREM I.V. is 500 mg given every 8 hours for skin and skin structure infections and 1 gram given every 8 hours for intra-abdominal infections. When treating complicated skin and skin structure infections caused by P.aeruginosa, a dose of 1 gram every 8 hours is recommended.
Pediatric Patients 3 Months of Age and Older: For pediatric patients 3 months of age and older, the MERREM I.V. dose is 10 mg/kg, 20 mg/kg or 40 mg/kg every 8 hours (maximum dose is 2 grams every 8 hours), depending on the type of infection (complicated skin and skin structure, intra-abdominal or meningitis). Pediatric patients weighing over 50 kg should be administered MERREM I.V. at a dose of 500 mg every 8 hours for complicated skin and skin structure infections, 1 gram every 8 hours for intra-abdominal infections and 2 grams every 8 hours for meningitis. MERREM I.V. should be given as intravenous infusion over approximately 15 minutes to 30 minutes or as an intravenous bolus injection (5 mL to 20 mL) over approximately 3 minutes to 5 minutes. There is limited safety data available to support the administration of a 40 mg/kg (up to a maximum of 2 grams) bolus dose.
Route of Administration:
Intravenous
In Vitro Use Guide
Curator's Comment: Meropenem was 4-64 times more active than imipenem against gram-negatives, including Enterobacteriaceae organisms, Pseudomonas aeruginosa, Burkholderia cepacia, Neisseria meningiditis, and Haemophilus influenzae. Imipenem was up to 2-4 times more active than meropenem against some gram-positive cocci, including Enterococcus faecalis. Meropenem, unlike imipenem or ceftazidime, was bactericidal for all strains of Enterobacteriaceae, P. aeruginosa, and gram-positive cocci tested at < or = 8 times the MIC.
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300000017633
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
