Meropenem

Meropenem

Systematic (IUPAC) name
3-[5-(dimethylcarbamoyl) pyrrolidin-2-yl] sulfanyl-6- (1-hydroxyethyl)-4-methyl-7-oxo- 1-azabicyclo[3.2.0] hept-2-ene-2-carboxylic acid
Clinical data
Trade names	Merrem
AHFS/Drugs.com	monograph
Pregnancy cat.	B(US)
Legal status	POM (UK) ℞-only (US)
Routes	IV
Pharmacokinetic data
Bioavailability	100%
Protein binding	Approximately 2%.
Half-life	1 hour
Excretion	Renal
Identifiers
CAS number	119478-56-7 Y
ATC code	J01DH02
PubChem	CID 441130
DrugBank	APRD01097
ChemSpider	389924 Y
UNII	FV9J3JU8B1 Y
KEGG	D02222 Y
ChEBI	CHEBI:43968 N
ChEMBL	CHEMBL127 Y
Chemical data
Formula	C17H25N3O5S
Mol. mass	383.464 g/mol
SMILES	eMolecules & PubChem
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 Y Key:DMJNNHOOLUXYBV-PQTSNVLCSA-N Y
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Meropenem is an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections, including meningitis and pneumonia. It is a beta-lactam and belongs to the subgroup of carbapenem, similar to imipenem and ertapenem. Meropenem was originally developed by Sumitomo Pharmaceuticals. It is marketed outside Japan by AstraZeneca with the brand names Merrem and Meronem. It gained US FDA approval in July 1996. It penetrates well into many tissues and body fluids including the cerebrospinal fluid, bile, heart valves, lung, and peritoneal fluid.^[1]

Mechanism of action

Meropenem is bactericidal except against Listeria monocytogenes where it is bacteriostatic. It inhibits bacterial wall synthesis like other beta-lactam antibiotics. In contrast to other beta-lactams, it is highly resistant to degradation by beta-lactamases or cephalosporinases. Resistance generally arises due to mutations in penicillin binding proteins, production of metallo-beta-lactamases, or resistance to diffusion across the bacterial outer membrane.^[2] Unlike imipenem, it is stable to dehydropeptidase-1 and can therefore be given without cilastatin.

Indications

The spectrum of action includes many gram-positive and gram-negative bacteria (including Pseudomonas) and anaerobic bacteria. The overall spectrum is similar to imipenem although meropenem is more active against Enterobacteriaceae and less active against gram-positive bacteria. It is also very resistant to extended-spectrum beta lactamases but may be more susceptible to metallo-beta-lactamases.^[1] Meropenem is frequently given in the treatment of febrile neutropenia. This condition frequently occurs in patients with hematological malignancies and cancer patients receiving anticancer drugs that cause bone marrow suppression..

Administration

Meropenem must be administered intravenously. It is supplied as a white crystalline powder to be dissolved in 5% monobasic potassium phosphate solution. Dosing must be adjusted for kidney function and for haemofiltration.^[3]

Common adverse effects

The most common adverse effects are diarrhea (4.8%), nausea and vomiting (3.6%), injection-site inflammation (2.4%), headache (2.3%), rash (1.9%), and thrombophlebitis (0.9%).^[2] Many of these adverse effects were observed in the setting of severely ill individuals who were already taking many medications. Meropenem also has a reduced potential for causing seizures in comparison with imipenem. Several cases of severe hypokalemia have been reported.^[4][5]

Trade names

Other trade names include Zwipen, Carbonem and Neomed (India), Mepem (Taiwan), Meropen (Japan, Korea) and Neopenem. [Merocon (Continental), Carnem (Laderly Biotech), PENRO (Bosch), Meronem (ICI) {Pakistan}]

References

1. ^ ^{a b} AHFS DRUG INFORMATION 2006 (2006 ed ed.). American Society of Health-System Pharmacists. 2006. 
2. ^ ^{a b} Mosby's Drug Consult 2006 (16 ed ed.). Mosby, Inc.. 2006. 
3. ^ Bilgrami, I.; Roberts, J. A.; Wallis, S. C.; Thomas, J.; Davis, J.; Fowler, S.; Goldrick, P. B.; Lipman, J. (2010). "Meropenem Dosing in Critically Ill Patients with Sepsis Receiving High Volume Continuous Veno-Venous Hemofiltration". Antimicrobial Agents and Chemotherapy 54 (7): 2974. doi:10.1128/AAC.01582-09. PMC 2897321. PMID 20479205. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2897321.  edit
4. ^ Margolin L. Impaired rehabilitation secondary to muscle weakness induced by meropenem. Clin. Drug Invest. 2004; 24(1):61-2.
5. ^ R Bharti, S Gombar, AK Khanna. Meropenem in critical care - uncovering the truths behind weaning failure. J Anaesth Clin Pharmacol 2010; 26(1): 99-101

External links

• MERREM I.V. (meropenem for injection) Official Site by AstraZeneca