U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H25N3O5S.3H2O
Molecular Weight 437.508
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEROPENEM

SMILES

O.O.O.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

InChI

InChIKey=CTUAQTBUVLKNDJ-OBZXMJSBSA-N
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

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H25N3O5S
Molecular Weight 383.463
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

PubMed

PubMed

TitleDatePubMed
Investigation of synergism of meropenem and ciprofloxacin against Pseudomonas aeruginosa and Acinetobacter strains isolated from intensive care unit infections.
2001
Piperacillin/tazobactam: a pharmacoeconomic review of its use in moderate to severe bacterial infections.
2001
[Antibiotic therapy of cystic fibrosis in children].
2001
[Antimicrobial activities and mechanisms of carbapenem resistance in clinical isolates of carbapenem-resistant Pseudomonas aeruginosa and Acinetobacter spp].
2001 Aug
[The high level resistance to carbapenems in Acinetobacter baumannii is a multifactorial problem].
2001 Aug-Sep
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].
2001 Dec
Antimicrobial susceptibility of respiratory isolates of Enterobacteriaceae and Staphylococcus aureus in Italy: incidence and trends over the period 1997-1999.
2001 Dec
Empirical monotherapy with meropenem in serious bacterial infections in children.
2001 Dec
Comparative in-vitro activity of carbapenem antibiotics against respiratory pathogens isolated between 1999 and 2000.
2001 Dec
Survey of antibiotic resistance in Pseudomonas aeruginosa by The Tokyo Johoku Association of Pseudomonas Studies.
2001 Dec
Meropenem pharmacokinetics in children and adolescents receiving hemodialysis.
2001 Dec
Unit differences in pathogen occurrence arising from the MYSTIC program European database (1997-2000).
2001 Dec
MYSTIC program: summary of European data from 1997 to 2000.
2001 Dec
Antimicrobial resistance trends in medical centers using carbapenems: report of 1999 and 2000 results from the MYSTIC program (USA).
2001 Dec
Determining the value of antimicrobial surveillance programs.
2001 Dec
MYSTIC (Meropenem Yearly Susceptibility Test Information Collection) conference. Hamburg, Germany, 10 May 2001.
2001 Dec
In-vitro activities of various antibiotics, alone and in combination with amikacin against Pseudomonas aeruginosa.
2001 Dec
A novel metallo-beta-lactamase, Mbl1b, produced by the environmental bacterium Caulobacter crescentus.
2001 Dec 14
[In vitro and in vivo activities of panipenem against penicillin-resistant Streptococcus pneumoniae].
2001 Jul
Use of broad spectrum antibiotics in six non-university Swiss hospitals.
2001 Jul 28
Ertapenem: a new carbapenem.
2001 Jun
[A case of eosinophilic pneumonia possibly due to ifenprodil].
2001 Nov
[Comparative antibacterial activity of carbapenems against P. aeruginosa (1)].
2001 Nov
Spectrum and activity of three contemporary fluoroquinolones tested against Pseudomonas aeruginosa isolates from urinary tract infections in the SENTRY Antimicrobial Surveillance Program (Europe and the Americas; 2000): more alike than different!
2001 Nov
In vitro and in vivo activities of meropenem and comparable antimicrobial agents against Haemophilus influenzae, including beta-lactamase-negative ampicillin-resistant strains.
2001 Nov
National shortages of antimicrobial agents: results of 2 surveys from the Infectious Diseases Society of America Emerging Infections Network.
2001 Nov 1
Influence of in-vivo endotoxin liberation on anti-anaerobic antimicrobial efficacy.
2001 Oct
Failure of cefotaxime and meropenem to eradicate meningitis caused by an intermediately susceptible Streptococcus pneumoniae strain.
2001 Oct
[A randomized, controlled clinical trial of meropenem and imipenem/cilastatin in the treatment of acute bacterial infections].
2001 Sep
[Susceptibility to penicillin and 13 antimicrobial agents in erythromycin-resistant viridans group streptococci isolated from blood cultures].
2001 Sep
[Pyogenic sacroiliitis in pregnancy].
2001 Sep
[Antimicrobial activities of carbapenems and fourth generation cephems against clinically isolated strains].
2001 Sep
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
Effect of meropenem on disposition kinetics of valproate and its metabolites in rabbits.
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
Synthesis and biological properties of new 1beta-methylcarbapenems containing heteroaromatic thioether moiety.
2001 Sep 3
Comparative in vitro activity of isepamicin and other antibiotics against gram-negative bacilli from intensive care units (ICU) in Belgium.
2001 Sep-Oct
Effects of cefepime and meropenem on the gastrointestinal colonization of surgical patients by Candida albicans.
2001 Sep-Oct
Antibiotic persistence: the role of spontaneous DNA repair response.
2001 Winter
Use of Etests with carbapenems for Gram-negative rods producing beta-lactamases.
2002 Feb
Pharmacokinetics and pharmacodynamics of meropenem in critically ill patients.
2002 Feb
Carbapenem-resistant Acinetobacter and role of curtains in an outbreak in intensive care units.
2002 Feb
In vitro activity of the aerosolized agents colistin and tobramycin and five intravenous agents against Pseudomonas aeruginosa isolated from cystic fibrosis patients in southwestern Germany.
2002 Feb
Meropenem stability to beta-lactamase hydrolysis and comparative in vitro activity against several beta-lactamase-producing Gram-negative strains.
2002 Feb
Acute necrotizing gastritis by Escherichia coli in a severely neutropenic patient.
2002 Jan
Antimicrobial susceptibilities among clinical isolates of extended-spectrum cephalosporin-resistant Gram-negative bacteria in a Taiwanese University Hospital.
2002 Jan
Primary liver abscess caused by one clone of Klebsiella pneumoniae with two colonial morphotypes and resistotypes.
2002 Jan
Antibiotic resistance among clinical isolates of Acinetobacter in the UK, and in vitro evaluation of tigecycline (GAR-936).
2002 Mar
Antibiotic-resistant gram-negative organisms in pediatric chronic-care facilities.
2002 Mar 15
Patents

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:48:20 UTC 2019
Edited
by admin
on Mon Oct 21 19:48:20 UTC 2019
Record UNII
FV9J3JU8B1
Record Status Validated (UNII)
Record Version
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Name Type Language
MEROPENEM
MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
ICI 194,660
Code English
MERREM I.V.
Brand Name English
MERONEM
Brand Name English
MEROPENEM TRIHYDRATE [WHO-DD]
Common Name English
MEROPENEM [USAN]
Common Name English
CARBAVANCE COMPONENT MEROPENEM
Brand Name English
MEROPENEM TRIHYDRATE
EP   MI   WHO-DD  
Common Name English
MEROPENEM HYDRATE [JAN]
Common Name English
MEROPENEM [VANDF]
Common Name English
(4R,5S,6S)-3-(((3S,5S)-5-(DIMETHYLCARBAMOYL)-3-PYRROLIDINYL)THIO)-6-((1R)-1-HYDROXYETHYL)-4-METHYL-7-OXO-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID, TRIHYDRATE
Common Name English
MEROPENEM HYDRATE
JAN  
Common Name English
MEROPENEM [USP-RS]
Common Name English
MEROPENEM (AS TRIHYDRATE)
Common Name English
MEROPENEM TRIHYDRATE [MI]
Common Name English
MEROPENEM [MART.]
Common Name English
SM-7338
Code English
MERREM
Brand Name English
MEROPENEM [ORANGE BOOK]
Common Name English
VABOMERE COMPONENT MEROPENEM
Brand Name English
MEROPENEM TRIHYDRATE [EP]
Common Name English
MEROPENEM COMPONENT OF CARBAVANCE
Brand Name English
1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID, 3-((5-((DIMETHYLAMINO)CARBONYL)-3-PYRROLIDINYL)THIO)-6-(1-HYDROXYETHYL)-4-METHYL-7-OXO-, TRIHYDRATE, (4R-(3(3S*,5S*),4.ALPHA.,5.BETA.,6.BETA.(R*)))-
Common Name English
MEROPENEM [USP]
Common Name English
ICI-194660
Code English
Classification Tree Code System Code
WHO-VATC QJ01DH02
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
NCI_THESAURUS C260
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
NDF-RT N0000175496
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
WHO-ATC J01DH02
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
WHO-ATC J01DH52
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
FDA ORPHAN DRUG 130799
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
LIVERTOX 604
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
Code System Code Type Description
PUBCHEM
441129
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
DRUG BANK
DB00760
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
WIKIPEDIA
MEROPENEM
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
ChEMBL
CHEMBL127
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
LactMed
119478-56-7
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
MERCK INDEX
M7240
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY Merck Index
EVMPD
SUB21617
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
EPA CompTox
119478-56-7
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
MESH
C059500
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
RXCUI
29561
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C1160
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
CAS
119478-56-7
Created by admin on Mon Oct 21 19:48:20 UTC 2019 , Edited by admin on Mon Oct 21 19:48:20 UTC 2019
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
Meropenem: approximately 40€“60% of dose was excreted unchanged within 24 to 48 hours with a further 28% recovered as the microbiologically inactive hydrolysis product; fecal elimination accounts for ~2% of dose.
PARENT -> SALT/SOLVATE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC