Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Meropenem: Difference between pages

{{Short description|Broad-spectrum antibiotic}}

{{Use mdy dates|date=February 2024}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

| Watchedfields = changed

| verifiedrevid = 462248901

| image = Meropenem structure.svg

| alt =

| alt2 =

| tradename = Merrem, others

| DailyMedID = Meropenem

| pregnancy_AU = B2

| routes_of_administration = [[Intravenous]]

| ATC_prefix = J01

| ATC_suffix = DH02

| legal_AU = S4

| legal_CA = Rx-only

| legal_CA_comment = <ref>{{cite web | title=Regulatory Decision Summary for Meropenem for Injection USP and Sodium Chloride Injection USP | website=Drug and Health Products Portal | date=4 January 2024 | url=https://dhpp.hpfb-dgpsa.ca/review-documents/resource/RDS1708462789662 | access-date=2 April 2024}}</ref>

| protein_bound = Approximately 2%

| excretion = [[Kidney]]

| ChEBI_Ref = {{ebicite|correct|EBI}}

| PDB_ligand = MEM

| IUPAC_name = (4''R'',5''S'',6''S'')-3-(((3''S'',5''S'')-5-(Dimethylcarbamoyl)pyrrolidin-3-yl)thio)-6-((''R'')-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

| C=17 | H=25 | N=3 | O=5 | S=1

<!-- Definition and medical uses -->

'''Meropenem''', sold under the brand name '''Merrem''' among others, is an [[intravenous]] [[carbapenem]] [[antibiotic]] used to treat a variety of [[bacterial infection]]s.<ref name=AHFS2017/> Some of these include [[meningitis]], [[intra-abdominal infection]], [[pneumonia]], [[sepsis]], and [[anthrax]].<ref name=AHFS2017>{{cite web|title=Meropenem|url=https://www.drugs.com/monograph/meropenem.html|publisher=The American Society of Health-System Pharmacists|access-date=December 8, 2017|archive-date=January 20, 2011|archive-url=https://web.archive.org/web/20110120143956/https://www.drugs.com/monograph/meropenem.html|url-status=live}}</ref>

<!-- Side effects and mechanisms -->

Common side effects include nausea, diarrhea, constipation, headache, rash, and pain at the site of injection.<ref name=AHFS2017/> Serious side effects include [[Clostridioides difficile infection|''Clostridioides difficile'' infection]], [[seizures]], and [[allergic reactions]] including [[anaphylaxis]].<ref name=AHFS2017/> Those who are allergic to other [[β-lactam antibiotic]]s are more likely to be allergic to meropenem as well.<ref name=AHFS2017/> Use in pregnancy appears to be safe.<ref name=AHFS2017/> It is in the [[carbapenem]] family of medications.<ref name=AHFS2017/> Meropenem usually results in [[Bactericidal|bacterial death]] through blocking their ability to make a [[cell wall]].<ref name=AHFS2017/> It is more resistant to breakdown by [[β-lactamase]] producing bacteria.<ref name=AHFS2017/>

<!-- History and culture -->

Meropenem was patented in 1983.<ref>{{cite book|vauthors=Fischer J, Ganellin CR|title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=978-3-527-60749-5|page=497|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA497|language=en|access-date=September 20, 2020|archive-date=February 27, 2024|archive-url=https://web.archive.org/web/20240227031509/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA497#v=onepage&q&f=false|url-status=live}}</ref> It was approved for medical use in the United States in 1996.<ref name=AHFS2017/> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref><ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> The World Health Organization classifies meropenem as critically important for human medicine.<ref>{{cite book | vauthors=((World Health Organization)) | year=2019 | title=Critically important antimicrobials for human medicine | edition=6th revision | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl=10665/312266 | isbn=978-92-4-151552-8 | hdl-access=free }}</ref>

== Medical uses ==

The spectrum of action includes many [[Gram-positive]] and [[Gram-negative]] bacteria (including ''[[Pseudomonas]]'') and [[Anaerobic organism|anaerobic]] bacteria. The overall spectrum is similar to that of imipenem, although meropenem is more active against [[Enterobacteriaceae]] and less active against Gram-positive bacteria. It works against extended-spectrum β-lactamases, but may be more susceptible to metallo-β-lactamases.<ref name=AHFS>{{ cite book | title= AHFS Drug Information | publisher= American Society of Health-System Pharmacists | year= 2006 | edition= 2006 }}</ref> 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 suppress [[bone marrow]] formation. It is approved for complicated skin and skin structure infections, complicated intra-abdominal infections and [[Meningitis|bacterial meningitis]].<ref name="auto">{{cite journal | url=https://doi.org/10.1086/590065 | doi=10.1086/590065 | title=Update on the Efficacy and Tolerability of Meropenem in the Treatment of Serious Bacterial Infections | date=2008 | journal=Clinical Infectious Diseases | volume=47 | pages=S41–S51 | pmid=18713049 | vauthors=Mohr Iii JF | access-date=February 23, 2024 | archive-date=February 27, 2024 | archive-url=https://web.archive.org/web/20240227031509/https://academic.oup.com/cid/article/47/Supplement_1/S41/305563 | url-status=live }}</ref><ref>{{Cite web |date=September 16, 2016 |title=Meropenem |url=https://medlineplus.gov/druginfo/meds/a696038.html |access-date=March 19, 2023 |website=MedlinePlus.gov |archive-date=March 19, 2023 |archive-url=https://web.archive.org/web/20230319204623/https://medlineplus.gov/druginfo/meds/a696038.html |url-status=live }}</ref><ref>{{Cite web | title = Merrem® IV (meropenem for injection) | work = Pediatric Postmarketing Pharmacovigilance Review | date = November 17, 2017 |url=https://www.fda.gov/media/110518/download | publisher = [[Food and Drug Administration]] |access-date=February 23, 2024|archive-date=March 5, 2021|archive-url=https://web.archive.org/web/20210305114129/https://www.fda.gov/media/110518/download|url-status=live}}</ref><ref>{{Cite web|url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/050706Orig1s034.pdf|title= Approval package for meropenem for injection |access-date=February 23, 2024|archive-date=April 12, 2021|archive-url=https://web.archive.org/web/20210412122257/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/050706Orig1s034.pdf|url-status=live}}</ref>

In 2017, the U.S. [[Food and Drug Administration]] (FDA) granted approval for the combination of [[meropenem/vaborbactam|meropenem and vaborbactam]] to treat adults with complicated [[urinary tract infections]].<ref>{{cite press release|title=FDA approves new antibacterial drug|url=https://www.fda.gov/news-events/press-announcements/fda-approves-new-antibacterial-drug|website=U.S. [[Food and Drug Administration]] (FDA)|date=March 24, 2020|access-date=March 5, 2022|archive-date=April 23, 2019|archive-url=https://web.archive.org/web/20190423191933/https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm573955.htm|url-status=live}} {{PD-notice}}</ref>

===Administration===

Meropenem is administered [[intravenous]]ly as an aqueous solution. Meropenem is stored in vials as white crystalline powder (containing meropenem as the trihydrate blended with anhydrous sodium carbonate).<ref>{{cite journal | url=https://doi.org/10.2165/00003495-200868060-00006 | doi=10.2165/00003495-200868060-00006 | title=Meropenem | date=2008 | journal=Drugs | volume=68 | issue=6 | pages=803–838 | pmid=18416587 | vauthors=Baldwin CM, Lyseng-Williamson KA, Keam SJ | access-date=February 23, 2024 | archive-date=February 27, 2024 | archive-url=https://web.archive.org/web/20240227031454/https://link.springer.com/article/10.2165/00003495-200868060-00006 | url-status=live }}</ref> For intravenous administration, the powder is dissolved in 5% [[Monopotassium phosphate|monobasic potassium phosphate]] solution, since meropenem is soluble in 5% monobasic potassium phosphate solution and only sparingly soluble in water ({{Value|5.63|u=mg/mL}}).<ref name="fda2008">{{Cite web|url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050706s022lbl.pdf|title=NDA 50-706/S-022 MERREM I.V.|access-date=February 21, 2024|archive-date=February 21, 2024|archive-url=https://web.archive.org/web/20240221102312/https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050706s022lbl.pdf|url-status=live}}</ref><ref>{{cite web | url=https://go.drugbank.com/salts/DBSALT002823 | title=Meropenem trihydrate {{pipe}} DrugBank Online | access-date=February 23, 2024 | archive-date=February 23, 2024 | archive-url=https://web.archive.org/web/20240223111434/https://go.drugbank.com/salts/DBSALT002823 | url-status=live }}</ref><ref>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Meropenem#section=Solubility | title=Meropenem | access-date=February 23, 2024 | archive-date=February 23, 2024 | archive-url=https://web.archive.org/web/20240223111434/https://pubchem.ncbi.nlm.nih.gov/compound/Meropenem#section=Solubility | url-status=live }}</ref> For intravenous bolus administration, injection vials are reconstituted with sterile water for injection.<ref name="fda2008"/>

Reconstituted (dissolved) meropenem degrades over time.<ref name="emc"/><ref name="pmid31205331">{{cite journal | url=https://doi.org/10.1177/0018578718779009 | doi=10.1177/0018578718779009 | title=Stability of Meropenem After Reconstitution for Administration by Prolonged Infusion | date=2019 | journal=Hospital Pharmacy | volume=54 | issue=3 | pages=190–196 | pmid=31205331 | pmc=6535930 | vauthors=Fawaz S, Barton S, Whitney L, Swinden J, Nabhani-Gebara S | access-date=February 22, 2024 | archive-date=February 27, 2024 | archive-url=https://web.archive.org/web/20240227031516/https://journals.sagepub.com/doi/10.1177/0018578718779009 | url-status=live }}</ref> The degradation may be associated with color change of the solution, typical for a hydrolysis of the [[amide bond]] of the β-lactam ring as seen with most β-lactam antibiotics,<ref name="pmid23163348">{{cite journal |vauthors=Palzkill T |title=Metallo-β-lactamase structure and function |journal=Ann N Y Acad Sci |volume=1277 |issue= 1|pages=91–104 |date=January 2013 |pmid=23163348 |pmc=3970115 |doi=10.1111/j.1749-6632.2012.06796.x|bibcode=2013NYASA1277...91P }}</ref> while particularly for merapenem the color is changing from colorless or pale yellow to vivid yellowish.<ref name="pmid26448659"/> Upon reconstitution, the merapenem infusion solution, prepared with 0.9% sodium chloride, exhibits both chemical and physical stability for a duration of 3 hours at a temperature up to {{Value|25}}°C. If refrigerated ({{Value|2|-|8}}°C), the stability extends to 24 hours. However, when the product is reconstituted in a 5% dextrose solution, it is used immediately to ensure its efficacy.<ref name="emc">{{cite web | url=https://www.medicines.org.uk/emc/product/9074/smpc#about-medicine | title=Meropenem 1g powder for solution for injection/Infusion - Summary of Product Characteristics (SMPC) - (Emc) | access-date=February 22, 2024 | archive-date=February 22, 2024 | archive-url=https://web.archive.org/web/20240222192556/https://www.medicines.org.uk/emc/product/9074/smpc#about-medicine | url-status=live }}</ref> The degradation of meropenem in a water-based solution is affected by factors such as pH, temperature, initial concentration, and the specific type of infusion solution used.<ref name="pmid26448659">{{cite journal |vauthors=Tomasello C, Leggieri A, Cavalli R, Di Perri G, D'Avolio A |title=In Vitro Stabilifighty Evaluation of Different Pharmaceutical Products Containing Meropenem |journal=Hosp Pharm |volume=50 |issue=4 |pages=296–303 |date=April 2015 |pmid=26448659 |pmc=4589882 |doi=10.1310/hpj5004-296}}</ref> Meropenem solutions should not be frozen.<ref name="drugs-meropenem">{{cite web | url=https://www.drugs.com/pro/meropenem.html | title=Meropenem: Package Insert | access-date=February 23, 2024 | archive-date=February 23, 2024 | archive-url=https://web.archive.org/web/20240223014439/https://www.drugs.com/pro/meropenem.html | url-status=live }}</ref><ref name="pmid31447546">{{cite journal |vauthors=Foy F, Luna G, Martinez J, Nizich Z, Seet J, Lie K, Sunderland B, Czarniak P |title=An investigation of the stability of meropenem in elastomeric infusion devices |journal=Drug Des Devel Ther |volume=13 |issue= |pages=2655–2665 |date=2019 |pmid=31447546 |pmc=6682764 |doi=10.2147/DDDT.S212052|doi-access=free }}</ref>

Meropenem is administered every 8 hours.<ref name="fda2008"/>

Dosing must be adjusted for altered kidney function and for [[haemofiltration]].<ref name="pmid20479205">{{cite journal | vauthors = Bilgrami I, Roberts JA, Wallis SC, Thomas J, Davis J, Fowler S, Goldrick PB, Lipman J | title = Meropenem dosing in critically ill patients with sepsis receiving high-volume continuous venovenous hemofiltration | journal = Antimicrobial Agents and Chemotherapy | volume = 54 | issue = 7 | pages = 2974–2978 | date = July 2010 | pmid = 20479205 | pmc = 2897321 | doi = 10.1128/AAC.01582-09 }}</ref>

Studies recomment application of meropenem therapeutic drug monitoring for optimal application.<ref name="pmid33533509">{{cite journal |vauthors=Steffens NA, Zimmermann ES, Nichelle SM, Brucker N |title=Meropenem use and therapeutic drug monitoring in clinical practice: a literature review |journal=J Clin Pharm Ther |volume=46 |issue=3 |pages=610–621 |date=June 2021 |pmid=33533509 |doi=10.1111/jcpt.13369 |url=|doi-access=free }}</ref>

As with other β-lactams antibiotics, the effectiveness of treatment depends on the amount of time during the dosing interval that the meropenem concentration is above the minimum inhibitory concentration for the bacteria causing the infection.<ref name=Yu2018>{{cite journal | vauthors = Yu Z, Pang X, Wu X, Shan C, Jiang S | title = Clinical outcomes of prolonged infusion (extended infusion or continuous infusion) versus intermittent bolus of meropenem in severe infection: A meta-analysis | journal = PLOS ONE | volume = 13 | issue = 7 | pages = e0201667 | date = 2018 | pmid = 30059536 | pmc = 6066326 | doi = 10.1371/journal.pone.0201667 | doi-access = free | bibcode = 2018PLoSO..1301667Y }}</ref> For β-lactams, including meropenem, prolonged intravenous administration is associated with lower mortality than bolus intravenous infusion in persons with whose infections are severe, or caused by bacteria that are less sensitive to meropenem, such as ''[[Pseudomonas aeruginosa]]''.<ref name=Yu2018/><ref>{{cite journal | vauthors = Vardakas KZ, Voulgaris GL, Maliaros A, Samonis G, Falagas ME | title = Prolonged versus short-term intravenous infusion of antipseudomonal β-lactams for patients with sepsis: a systematic review and meta-analysis of randomised trials | journal = The Lancet. Infectious Diseases | volume = 18 | issue = 1 | pages = 108–120 | date = January 2018 | pmid = 29102324 | doi = 10.1016/S1473-3099(17)30615-1 }}</ref>

Meropenem exhibit poor permeability across the gut and low oral bioavailability because of its hydrophilic properties, which inhibit its passive diffusion across the intestinal epithelium.<ref name="pmid33197621">{{cite journal |vauthors=Raza A, Ngieng SC, Sime FB, Cabot PJ, Roberts JA, Popat A, Kumeria T, Falconer JR |title=Oral meropenem for superbugs: challenges and opportunities |journal=Drug Discov Today |volume=26 |issue=2 |pages=551–560 |date=February 2021 |pmid=33197621 |doi=10.1016/j.drudis.2020.11.004 |s2cid=226988098 |url=}}</ref> The challenges related to research of oral delivery of meropenem are related to high susceptibility of meropenem to degradation through hydrolysis of the amide bond in the β-lactam ring, even at relatively low temperatures and humidity.<ref name="pmid33197621"/> This instability can result in the loss of meropenem's antibacterial activity. Besides that, neropenem is unstable in the acidic environment of the stomach, leading to extensive degradation and loss of the drug after oral administration.<ref name="pmid33197621"/> In addition, intestinal efflux (secretory) transport can pump the drug back into the gut: efflux transporters, particularly P-glycoprotein (P-gp), present in the gastrointestinal tract can actively pump meropenem back into the gut lumen, limiting its absorption and reducing oral bioavailability; in the attempts of oral administration bacteria can develop resistance to meropenem by enhancing the active efflux of the antibiotic through efflux transporters, such as the MexAB-OprM tripartite efflux system in Pseudomonas aeruginosa.<ref name="pmid33197621"/> That's why meropenem is administered intravenously.<ref name="pmid33197621"/>

There is insufficient data regarding the administration of meropenem during breastfeeding. However, it has been observed that, in general, the concentration of this beta-lactam antibiotic in breast milk is relatively low, therefore, beta-lactam antibiotics are not anticipated to induce detrimental effects in infants who are breastfed. Nonetheless, there have been sporadic reports of disturbances in the gastrointestinal flora of the infant, manifesting as diarrhea or oral candidiasis (thrush), associated with the use of beta-lactam antibiotics, however, these potential side effects have not been thoroughly investigated specifically in the context of meropenem use, therefore, the safety profile of meropenem in breastfeeding mothers and their infants is unknown.<ref>{{cite web | url=https://pubmed.ncbi.nlm.nih.gov/30000076/ | pmid=30000076 | date=2006 | title=Meropenem | publisher=National Institute of Child Health and Human Development | access-date=February 21, 2024 | archive-date=February 21, 2024 | archive-url=https://web.archive.org/web/20240221104937/https://pubmed.ncbi.nlm.nih.gov/30000076/ | url-status=live }}</ref>

Although merapenem is not approved for intramuscular or subcutaneous routes of administration in humans, there were studies that evaluated the drug bioavailability in cats and reported biovailablity of 99.69% for intramuscular route and 96.52 % for subcutaneous route of administration; these studies also compared elimination half-lives for intravenous, intramuscular or subcutaneous routes of administration in cats and reported duration of 1.35, 2.10 and 2.26 hours, respectively.<ref name="pmid8815553">{{cite journal |vauthors=Tallarigo C, Comunale L, Baldassarre R, Poletti G |title=[Multicenter comparative study of meropenem vs. imipenem in the intramuscular treatment of hospital infections of the urinary tract] |language=it |journal=Minerva Urol Nefrol |volume=47 |issue=3 |pages=147–56 |date=September 1995 |pmid=8815553 |doi= |url=}}</ref> There was also a small study on local tolerance of meropenem intramuscrular administration in humans, and it was reported as generally good.<ref name="pmid8815553"/><ref name="pmid25751198">{{cite journal |vauthors=Meaney-Delman D, Bartlett LA, Gravett MG, Jamieson DJ |title=Oral and intramuscular treatment options for early postpartum endometritis in low-resource settings: a systematic review |journal=Obstet Gynecol |volume=125 |issue=4 |pages=789–800 |date=April 2015 |pmid=25751198 |doi=10.1097/AOG.0000000000000732 |url=}}</ref><ref name="pmid9410074">{{cite journal |vauthors=Lizasoaín M, Noriega AR |title=[Tolerance and safety of carbapenems: the use of meropenem] |language=es-ES |journal=Enferm Infecc Microbiol Clin |volume=15 |issue= Suppl 1|pages=73–7 |date=September 1997 |pmid=9410074 |doi= |url=}}</ref>

==Side 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%).<ref name=Mosby/> Many of these adverse effects were observed in severely ill individuals already taking many medications including [[vancomycin]].<ref>{{cite journal|vauthors=Erden M, Gulcan E, Bilen A, Bilen Y, Uyanik A, Keles M|title=Pancytopenýa and Sepsýs due to Meropenem: A Case Report|journal=Tropical Journal of Pharmaceutical Research|date=March 7, 2013|volume=12|issue=1|doi=10.4314/tjpr.v12i1.21|url=http://www.tjpr.org/vol12_no1/2013_12_1_21.pdf|doi-access=free|access-date=April 20, 2013|archive-date=November 13, 2013|archive-url=https://web.archive.org/web/20131113075104/http://www.tjpr.org/vol12_no1/2013_12_1_21.pdf|url-status=live}}</ref><ref>{{cite web|url=http://www.ehealthme.com/meropenem/meropenem-side-effects|title=Meropenem side effects - from FDA reports|publisher=eHealthMe|access-date=April 20, 2013|archive-date=November 5, 2013|archive-url=https://web.archive.org/web/20131105190936/http://www.ehealthme.com/meropenem/meropenem-side-effects|url-status=dead}}</ref> Meropenem has a reduced potential for seizures in comparison with [[imipenem]]. Several cases of severe [[hypokalemia]] have been reported.<ref name="pmid17516692">{{cite journal | vauthors = Margolin L | title = Impaired rehabilitation secondary to muscle weakness induced by meropenem | journal = Clinical Drug Investigation | volume = 24 | issue = 1 | pages = 61–62 | year = 2004 | pmid = 17516692 | doi = 10.2165/00044011-200424010-00008 | s2cid = 44484294 }}</ref><ref>{{cite journal|vauthors=Bharti R, Gombar S, Khanna AK|title=Meropenem in critical care - uncovering the truths behind weaning failure|journal=Journal of Anaesthesiology Clinical Pharmacology|year=2010|volume=26|issue=1|pages=99–101|doi=10.4103/0970-9185.75131|s2cid=54127805|url=http://www.joacp.org/article.asp?issn=0970-9185;year=2010;volume=26;issue=1;spage=99;epage=101;aulast=Bharti;type=0|doi-access=free|access-date=December 15, 2013|archive-date=February 21, 2015|archive-url=https://web.archive.org/web/20150221143859/http://www.joacp.org/article.asp?issn=0970-9185;year=2010;volume=26;issue=1;spage=99;epage=101;aulast=Bharti;type=0|url-status=live}}</ref>

== Interactions ==

Meropenem rapidly reduces serum concentrations of [[valproic acid]]. As a result, people who use valproic acid for [[epilepsy]] are at increased risk of [[seizures]] during treatment with meropenem. In situations where the use of meropenem cannot be avoided, prescription of an additional [[anticonvulsant]] should be considered.<ref>{{cite journal | vauthors = Al-Quteimat O, Laila A | title = Valproate Interaction With Carbapenems: Review and Recommendations | journal = Hospital Pharmacy | volume = 55 | issue = 3 | pages = 181–187 | date = June 2020 | pmid = 32508355 | pmc = 7243600 | doi = 10.1177/0018578719831974 }}</ref>

==Pharmacology==

===Mechanism of action===

Meropenem is [[bactericidal]] except against ''[[Listeria monocytogenes]]'', where it is [[Bacteriostatic agent|bacteriostatic]]. It inhibits bacterial cell wall synthesis like other β-lactam antibiotics. In contrast to other beta-lactams, it is highly resistant to degradation by [[Beta-lactamase|β-lactamase]]s or cephalosporinases. In general, resistance arises due to mutations in [[penicillin-binding proteins]], production of metallo-β-lactamases, or resistance to diffusion across the bacterial outer membrane.<ref name=Mosby>{{ cite book | title=Mosby's Drug Consult 2006 | publisher= Mosby, Inc. | year= 2006 | edition= 16}}</ref> Unlike [[imipenem]], it is stable to [[dehydropeptidase]]-1, so can be given without [[cilastatin]].

In 2016, a synthetic peptide-conjugated [[Morpholino|PMO]] (PPMO) was found to inhibit the expression of [[New Delhi metallo-beta-lactamase 1|New Delhi metallo-beta-lactamase]], an enzyme that many drug-resistant bacteria use to destroy carbapenems.<ref>{{Cite web|url=http://newatlas.com/molecule-weakens-superbugs-immunity-antibiotics/47483|title=New molecule knocks out superbugs' immunity to antibiotics|website=newatlas.com|date=January 20, 2017|access-date=January 25, 2017|archive-date=January 22, 2017|archive-url=https://web.archive.org/web/20170122155022/http://newatlas.com/molecule-weakens-superbugs-immunity-antibiotics/47483/|url-status=live}}</ref><ref>{{cite journal | vauthors = Sully EK, Geller BL, Li L, Moody CM, Bailey SM, Moore AL, Wong M, Nordmann P, Daly SM, Sturge CR, Greenberg DE | title = Peptide-conjugated phosphorodiamidate morpholino oligomer (PPMO) restores carbapenem susceptibility to NDM-1-positive pathogens in vitro and in vivo | journal = The Journal of Antimicrobial Chemotherapy | volume = 72 | issue = 3 | pages = 782–790 | date = March 2017 | pmid = 27999041 | pmc = 5890718 | doi = 10.1093/jac/dkw476 }}</ref>

While β-lactam ring in meropenem is more accessible to water molecules than in the other β-lactam antibiotics, that facilitates the hydrolysis process and faster degradation of meropenem's antibacterial properties in aqueous solutions, it is more resistant to degradation by β-lactamase enzymes produced by bacteria than the other β-lactam antibiotics.<ref>{{cite journal | url=https://doi.org/10.1093/jac/49.2.395 | doi=10.1093/jac/49.2.395 | title=Meropenem stability to beta-lactamase hydrolysis and comparative in vitro activity against several beta-lactamase-producing Gram-negative strains | date=2002 | journal=Journal of Antimicrobial Chemotherapy | volume=49 | issue=2 | pages=395–398 | pmid=11815587 | vauthors=Franceschini N, Segatore B, Perilli M, Vessillier S, Franchino L, Amicosante G | access-date=February 23, 2024 | archive-date=February 27, 2024 | archive-url=https://web.archive.org/web/20240227031503/https://academic.oup.com/jac/article/49/2/395/781461 | url-status=live }}</ref><ref name="auto"/>

==Research directions==

Nebulized meropenem (inhaled route) is researched, but is not approved, for prevention of bronchiectasis exacerbation.<ref>{{cite book | chapter-url=https://thorax.bmj.com/content/78/Suppl_4/A175.1 | doi=10.1136/thorax-2023-BTSabstracts.266 | chapter=P114 Nebulised meropenem for prevention of bronchiectasis exacerbation | title='It's not easy being green' – Suppurative lung diseases | date=2023 | vauthors = Nadeem I, Ingle T, Ur Rasool M, Mahdi N, Ul Munamm SA, Rabiei B, Vijayabarathy R, Grady D, Pai S, Grogono D | volume=78 | issue=Suppl 4 | pages=A175.1–A175 | access-date=February 21, 2024 | archive-date=February 21, 2024 | archive-url=https://web.archive.org/web/20240221102953/https://thorax.bmj.com/content/78/Suppl_4/A175.1 | url-status=live }}</ref>

==Society and culture==

[[File:Meropenem 1.jpg|thumb|right|Meropenem vial]]

===Trade names===

{| class="wikitable"

|+ Trade names

! Country !! Name !! Maker

|-

| India || UNOMERO || Scutonix Lifesciences, Bombay

|-

| India || Inzapenum || Dream India

|-

| || || Aurobindo Pharma

|-

| || Penmer || Biocon

|-

| || Meronir || Nirlife

|-

| || Merowin || Strides Acrolab

|-

| || Aktimer || Aktimas Biopharmaceuticals

|-

| || Neopenem || Neomed

|-

| || Mexopen || Samarth life sciences

|-

| || Meropenia || SYZA Health Sciences LLP

|-

| || Ivpenem || Medicorp Pharmaceuticals

|-

| || Merofit ||

|-

| || Lykapiper || Lyka Labs

|-

| || Winmero || Parabolic Drugs

|-

| Bangladesh

|-

| || '''Meroject''' || Eskayef Pharmaceuticals Ltd.

|-

| || '''Merocon''' || Beacon Pharmaceuticals

|-

| Indonesia || Merofen || Kalbe

|-

| Brazil || Zylpen || Aspen Pharma

|-

| Japan, Korea || Meropen ||

|-

| Australia || Merem ||

|-

| Taiwan || Mepem ||

|-

| Germany || Meronem ||

|-

| Nigeria || Zironem || Lyn-Edge Pharmaceuticals

|-

| Ukraine<ref>{{cite web |title=Меропенем (Meropenemum) |url=https://compendium.com.ua/uk/akt/77/739/meropenemum/ |website=compendium.com.ua |publisher=Compendium |access-date=May 21, 2022 |language=uk |archive-date=May 20, 2022 |archive-url=https://web.archive.org/web/20220520082943/https://compendium.com.ua/uk/akt/77/739/meropenemum/ |url-status=live }}</ref> || Meropenem || Lekhim-Kharkiv

|-

| || Panlaktam (Panlaktam) || "Darnytsia"

|-

| || Mepenam || Kyivmedpreparat

|-

| || Merobicide || Borshchahiv HFZ

|-

| US ||Meronem ||AstraZeneca

|-

| Indonesia || Merosan || Sanbe Farma

|-

| Indonesia || Merobat || Interbat

|-

| || Zwipen ||

|-

| || Carbonem ||

|-

| || Ronem ||Opsonin Pharma, BD

|-

| || Neopenem ||

|-

| || Merocon ||Continental

|-

| || Carnem || Laderly Biotech

|-

| || Penro || Bosch

|-

| ||Meroza || German Remedies

|-

| || Merotrol || Lupin)

|-

| || Meromer || Orchid Chemicals

|-

| || Mepenox || BioChimico

|-

| || Meromax || Eurofarma

|-

| || Ropen || Macter

|-

| || mirage || adwic

|-

| || Meropex || Apex Pharma Ltd.

|-

|

|Merostarkyl

|Hefny Pharma Group<ref>{{Cite web|url=http://hefnypharmagroup.info/en/therapeuticAreas/Hospital-line/99/Merostarkyl-500-mg|title=Hefny Pharma Group|website=hefnypharmagroup.info|access-date=May 22, 2018|archive-date=May 23, 2018|archive-url=https://web.archive.org/web/20180523101122/http://hefnypharmagroup.info/en/therapeuticAreas/Hospital-line/99/Merostarkyl-500-mg|url-status=live}}</ref>

|}

== References ==

{{reflist}}

{{CephalosporinAntiBiotics}}

{{Portal bar|Medicine}}

[[Category:Carbapenem antibiotics]]

[[Category:Enantiopure drugs]]

[[Category:Carboxamides]]

[[Category:Drugs developed by AstraZeneca]]

[[Category:Pyrrolidines]]

[[Category:Secondary alcohols]]

[[Category:World Health Organization essential medicines]]

[[Category:Wikipedia medicine articles ready to translate]]