You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameMeropenem
Accession NumberDB00760  (APRD01097, EXPT02153)
TypeSmall Molecule
GroupsApproved, Investigational
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
Synonyms
(1R,5S,6S)-2-[(3S,5S)-5-DIMETHYLAMINOCARBONYLPYRROLIDIN-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid
(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Antibiotic sm 7338
Meropenem
Meropenem anhydrous
Meropenem Hydrate
Meropenem trihydrate
Meropenemum
Meropenemum trihydricum
External Identifiers
  • ICI 194660
  • SM 7338
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Meropenem for Injectionpowder for solution500 mgintravenousFresenius Kabi Canada Ltd2014-10-20Not applicableCanada
Meropenem for Injectionpowder for solution1 gintravenousFresenius Kabi Canada Ltd2014-06-05Not applicableCanada
Meropenem for Injectionpowder for solution1 gintravenousSandoz Canada Incorporated2012-01-26Not applicableCanada
Meropenem for Injectionpowder for solution500 mgintravenousSandoz Canada Incorporated2012-01-26Not applicableCanada
Meropenem for Injection Sdzpowder for solution1 gintravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Meropenem for Injection Sdzpowder for solution500 mgintravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Meropenem for Injection USPpowder for solution500 mgintravenousSterimax IncNot applicableNot applicableCanada
Meropenem for Injection USPpowder for solution1 gintravenousSterimax Inc2015-06-11Not applicableCanada
Meropenem for Injection USPpowder for solution500 mgintravenousHospira Healthcare Corporation2015-03-17Not applicableCanada
Meropenem for Injection USPpowder for solution1 gintravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Merrem - Add-vantage Vials - Pws IV 1 G/vialpowder for solution1 gintravenousAstrazeneca Canada IncNot applicableNot applicableCanada
Merrem - Add-vantage Vials-pws IV 500 Mg/vialpowder for solution500 mgintravenousAstrazeneca Canada IncNot applicableNot applicableCanada
Merrem IVinjection1 g/30mLintravenousAstra Zeneca Pharmaceuticals Lp1996-09-23Not applicableUs
Merrem IVinjection500 mg/20mLintravenousAstra Zeneca Pharmaceuticals Lp1996-09-23Not applicableUs
Merrem Pws IV 1 G/vialpowder for solution1 gintravenousAstrazeneca Canada Inc1996-11-12Not applicableCanada
Merrem Pws IV 500 Mg/vialpowder for solution500 mgintravenousAstrazeneca Canada Inc1996-11-08Not applicableCanada
Ran-meropenempowder for solution1 gintravenousRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Ran-meropenempowder for solution500 mgintravenousRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Meropeneminjection, powder, for solution500 mg/10mLintravenousFresenius Kabi USA, LLC2011-10-14Not applicableUs
Meropeneminjection, powder, for solution500 mg/10mLintravenousHospira, Inc.2010-06-23Not applicableUs
Meropeneminjection, powder, for solution1 g/20mLintravenousCardinal Health2010-06-23Not applicableUs
Meropeneminjection, powder, for solution500 mg/10mLintravenousCardinal Health2010-06-23Not applicableUs
Meropeneminjection, powder, for solution1 g/30mLintravenousDaewoong Pharmaceutical Co., Ltd.2015-12-18Not applicableUs
Meropeneminjection, powder, for solution500 mg/20mLintravenousDaewoong Pharmaceutical Co., Ltd.2015-12-18Not applicableUs
Meropeneminjection, powder, for solution1 g/20mLintravenousSandoz Inc2011-03-29Not applicableUs
Meropeneminjection, powder, for solution500 mg/10mLintravenousSandoz Inc2011-03-29Not applicableUs
Meropeneminjection, powder, for solution1 g/20mLintravenousFresenius Kabi USA, LLC2011-10-26Not applicableUs
Meropeneminjection, powder, for solution1 g/20mLintravenousHospira, Inc.2010-06-23Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AronemACI
AropenAristopharma
CarbanemSanofi-Aventis
EropeLincoln
FulspecAcme
I-penamIncepta
MerenzAdmac
MerofitFHC
MeronemAstraZeneca
MeronisNeiss
MeropenSwiss Parenterals
MerotecZuventus
MerremAstraZeneca
Merrem I.V.AstraZeneca
MonanAstraZeneca
RopenemDrug International
ZeropenemSanofi-Aventis
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIFV9J3JU8B1
CAS number119478-56-7
WeightAverage: 383.463
Monoisotopic: 383.151491615
Chemical FormulaC17H25N3O5S
InChI KeyInChIKey=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
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
[H][C@]1([C@@H](C)O)C(=O)N2C(C(O)=O)=C(S[C@@H]3CN[C@@H](C3)C(=O)N(C)C)[[email protected]](C)[C@]12[H]
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentThienamycins
Alternative Parents
Substituents
  • Thienamycin
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Pyrroline carboxylic acid or derivatives
  • Pyrroline carboxylic acid
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • Azepine
  • Vinylogous thioester
  • Tertiary carboxylic acid amide
  • Pyrroline
  • Pyrrolidine
  • Thioenolether
  • Tertiary amine
  • Secondary alcohol
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Sulfenyl compound
  • Thioether
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsMeropenem 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 actionThe 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingApproximately 2%.
Metabolism

Primarily excreted unchanged. There is one metabolite which is microbiologically inactive.

Route of eliminationApproximately 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 lifeApproximately 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.
ClearanceNot Available
ToxicityIn 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7086
Blood Brain Barrier-0.9901
Caco-2 permeable-0.6556
P-glycoprotein substrateSubstrate0.8057
P-glycoprotein inhibitor INon-inhibitor0.6779
P-glycoprotein inhibitor IINon-inhibitor0.952
Renal organic cation transporterNon-inhibitor0.9053
CYP450 2C9 substrateNon-substrate0.8286
CYP450 2D6 substrateNon-substrate0.8136
CYP450 3A4 substrateSubstrate0.6007
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9559
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9798
Ames testNon AMES toxic0.68
CarcinogenicityNon-carcinogens0.8623
BiodegradationNot ready biodegradable0.8801
Rat acute toxicity1.9158 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9969
hERG inhibition (predictor II)Non-inhibitor0.8683
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Hospira inc
  • Astrazeneca uk ltd
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionintravenous1 g/20mL
Injection, powder, for solutionintravenous1 g/30mL
Injection, powder, for solutionintravenous500 mg/10mL
Injection, powder, for solutionintravenous500 mg/20mL
Injectionintravenous1 g/30mL
Injectionintravenous500 mg/20mL
Powder for solutionintravenous1 g
Powder for solutionintravenous500 mg
Prices
Unit descriptionCostUnit
Merrem 1 gm Solution Vial81.32USD vial
Merrem iv 1 gm vial78.19USD vial
Merrem 500 mg Solution Vial48.79USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1322371 No1993-09-212010-09-21Canada
US4943569 No1993-06-212010-06-21Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilitySparinglyNot Available
logP-0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.63 mg/mLALOGPS
logP-0.69ALOGPS
logP-4.4ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.18 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.89 m3·mol-1ChemAxon
Polarizability39.29 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Yoon Seok Song, Sung Woo Park, Yeon Jung Yoon, Hee Kyoon Yoon, Seong Cheol Moon, Byung Goo Lee, Soo Jin Choi, Sun Ah Jun, “METHOD FOR PREPARING MEROPENEM USING ZINC POWDER.” U.S. Patent US20120065392, issued March 15, 2012.

US20120065392
General ReferencesNot Available
External Links
ATC CodesJ01DH02
AHFS Codes
  • 08:12.07.08
PDB EntriesNot Available
FDA labelDownload (276 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Meropenem.
ProbenecidThe serum concentration of Meropenem can be increased when it is combined with Probenecid.
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Meropenem.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
Gene Name:
dacB
Uniprot ID:
P24228
Molecular Weight:
51797.85 Da
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:17139284 ]
  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:17016423 ]
  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:9099227 ]
  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:11353613 ]

Enzymes

Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
unknown
Actions
substrate
General Function:
Penicillin binding
Specific Function:
Hydrolyzes both carbenicillin and oxacillin.
Gene Name:
bla
Uniprot ID:
P14489
Molecular Weight:
29506.575 Da
References
  1. Pryka RD, Haig GM: Meropenem: a new carbapenem antimicrobial. Ann Pharmacother. 1994 Sep;28(9):1045-54. [PubMed:7803882 ]
  2. Bonfiglio G, Russo G, Nicoletti G: Recent developments in carbapenems. Expert Opin Investig Drugs. 2002 Apr;11(4):529-44. [PubMed:11922861 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on January 03, 2014 11:57