Ertapenem

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Antibiotic medication

title: "Ertapenem" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["carbapenem-antibiotics", "benzoic-acids", "anilides", "drugs-developed-by-merck-&-co.", "pyrrolidines"] description: "Antibiotic medication" topic_path: "general/carbapenem-antibiotics" source: "https://en.wikipedia.org/wiki/Ertapenem" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Antibiotic medication ::

::data[format=table title="Infobox drug"]

FieldValue
Verifiedfieldschanged
verifiedrevid461095141
imageErtapenem skeletal structure.svg
image_classskin-invert-image
image2Ertapenem ball-and-stick model.png
image_class2bg-transparent
tradenameInvanz
Drugs.com
MedlinePlusa614001
DailyMedIDErtapenem
pregnancy_AUB3
pregnancy_AU_comment
routes_of_administrationIntramuscular, intravenous
ATC_prefixJ01
ATC_suffixDH03
legal_AUS4
legal_AU_comment
legal_BR
legal_CA
legal_DE
legal_NZ
legal_UKPOM
legal_UK_comment
legal_USRx-only
legal_US_comment
legal_EURx-only
legal_EU_comment
legal_UN
legal_status
bioavailability90% (intramuscular)
protein_boundInversely proportional to concentration; 85 to 95%
metabolismHydrolysis of beta-lactam ring, CYP not involved
elimination_half-life4 hours
excretionKidney (80%) and fecal (10%)
CAS_number_Ref
CAS_number153832-46-3
PubChem150610
DrugBank_Ref
DrugBankDB00303
ChemSpiderID_Ref
ChemSpiderID132758
UNII_Ref
UNIIG32F6EID2H
KEGG_Ref
KEGGD04049
ChEBI_Ref
ChEBI404903
ChEMBL_Ref
ChEMBL1359
IUPAC_name(4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
C22
SMILESO=C(O)c1cc(ccc1)NC(=O)[C@H]4NCC@@HC4
StdInChI_Ref
StdInChI1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1
StdInChIKey_Ref
StdInChIKeyJUZNIMUFDBIJCM-ANEDZVCMSA-N
::

| Verifiedfields = changed | verifiedrevid = 461095141 | image = Ertapenem skeletal structure.svg | image_class = skin-invert-image | width = | alt = | caption = | image2 = Ertapenem ball-and-stick model.png | image_class2 = bg-transparent

| pronounce = | tradename = Invanz | Drugs.com = | MedlinePlus = a614001 | DailyMedID = Ertapenem | pregnancy_AU = B3 | pregnancy_AU_comment = | pregnancy_category= | routes_of_administration = Intramuscular, intravenous | class = | ATC_prefix = J01 | ATC_suffix = DH03 | ATC_supplemental =

| legal_AU = S4 | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =

| bioavailability = 90% (intramuscular) | protein_bound = Inversely proportional to concentration; 85 to 95% | metabolism = Hydrolysis of beta-lactam ring, CYP not involved | metabolites = | onset = | elimination_half-life = 4 hours | duration_of_action = | excretion = Kidney (80%) and fecal (10%)

| CAS_number_Ref = | CAS_number = 153832-46-3 | PubChem = 150610 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = DB00303 | ChemSpiderID_Ref = | ChemSpiderID = 132758 | UNII_Ref = | UNII = G32F6EID2H | KEGG_Ref = | KEGG = D04049 | ChEBI_Ref = | ChEBI = 404903 | ChEMBL_Ref = | ChEMBL = 1359 | NIAID_ChemDB = | PDB_ligand = | synonyms =

| IUPAC_name = (4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid | C=22 | H=25 | N=3 | O=7 | S=1 | SMILES = O=C(O)c1cc(ccc1)NC(=O)[C@H]4NCC@@HC4 | StdInChI_Ref = | StdInChI = 1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1 | StdInChI_comment = | StdInChIKey_Ref = | StdInChIKey = JUZNIMUFDBIJCM-ANEDZVCMSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation =

Ertapenem, sold under the brand name Invanz, is a carbapenem antibiotic medication used for the treatment of infections of the abdomen, the lungs, the upper part of the female reproductive system, and the diabetic foot.

The most common side effects include diarrhoea, nausea, headache, and problems around the area where the medicine is infused. It can significantly reduce the concentrations of valproic acid, an anti-seizure medication, in the blood to the point where it loses its effectiveness.

Ertapenem was approved for medical use in the United States in November 2001, and in the European Union in April 2002. It is marketed by Merck.

Medical uses

Ertapenem is indicated for the treatment of intra-abdominal infections, community-acquired pneumonia, pelvic infections, and diabetic foot infections, with bacteria that are susceptible to this drug, or expected to be so. It can also be used to prevent infections after colorectal surgery. In the United States it is also indicated for the treatment of complicated urinary tract infections including pyelonephritis. It is a potential effective alternative treatment for ceftriaxone-resistant gonorrhoea.

It is given as an intravenous infusion or intramuscular injection. The drug is not approved for children under three months of age.

Contraindications

The drug is contraindicated in people with known hypersensitivity to ertapenem or other carbapenem type antibiotics, or with severe hypersensitivity reactions (such as anaphylaxis or severe skin reactions) to other beta-lactam antibiotics in the past.

Side effects

Common side effects are diarrhoea (in 5% of people receiving ertapenem), nausea (in 3%) and vomiting, reactions at the injection site (5%, including pain and inflammation of the vein), and headache. Uncommon but possibly serious side effects include candida infections, seizures, skin reactions such as rashes (including nappy rash in children), and anaphylaxis. Hypersensitivity cross-reactions with penicillins are rare.

Ertapenem also can have an effect on some blood tests such as liver enzymes and platelet count.

Overdose

Overdosing is unlikely. In adults receiving the threefold therapeutic dose over eight days, no significant toxicity was observed.

Interactions

Ertapenem can reduce the concentrations of valproic acid, an epilepsy medication, by 70% and perhaps up to 95% within 24 hours; this can result in inadequate control of seizures. The effect is described for other carbapenem antibiotics as well, but seems to be most pronounced for ertapenem and meropenem. This is likely caused by several mechanisms: carbapenems inhibit transport of valproic acid from the gut into the body; they may increase metabolization of valproic acid to its glucuronide; they may reduce enterohepatic circulation and recycling of valproic acid glucuronide by acting against gut bacteria; and they may block transporter proteins that pump valproic acid out of red blood cells into the blood plasma. The effect is also seen in reverse: in cases where ertapenem has been withdrawn blood concentrations of valproate have been reported to rise.

Drug interactions via the cytochrome P450 enzyme system or the P-glycoprotein transporter are considered unlikely, as these proteins are not involved in the metabolism of ertapenem.

Pharmacology

Mechanism of action

Main article: β-lactam antibiotic#Mechanism of action

Like all beta-lactam antibiotics, ertapenem is bactericidal. It inhibits cross-linking of the peptidoglycan layer of bacterial cell walls by blocking a type of enzymes called penicillin-binding proteins (PBPs). When a bacterial cell tries to synthesize new cell wall in order to grow and divide, the attempt fails, rendering the cell vulnerable to osmotic disruption. Additionally, the surplus of peptidoglycan precursors triggers autolytic enzymes of the bacterium, which disintegrate the existing wall.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/e/e3/Penicillin_spheroplast_generation_horizontal.svg" caption="hdl = 10059/2129 }}"] ::

Susceptible bacteria

Bacteria that are normally susceptible to ertapenem treatment (at least in Europe) include:

Resistance

Bacteria that show no clinically relevant response to ertapenem include methicillin-resistant Staphylococcus species (including MRSA) as well as Acinetobacter, Aeromonas, Enterococcus, and Pseudomonas.

Microorganisms can become resistant to ertapenem by producing carbapenemases, enzymes that inactivate the drug by opening the beta-lactam ring. Other mechanisms of resistance against carbapenems are development of efflux pumps that transport the antibiotics out of the bacterial cells, mutations of PBPs, and mutations of Gram-negative bacteria's porins which are necessary for carbapenems to enter the bacteria.

Pharmacokinetics

::figure[src="https://upload.wikimedia.org/wikipedia/commons/c/c4/Ertapenem_open-ring_metabolite.svg" caption="id = CID 45105276 }}"] ::

The route of administration has only a slight effect on the drug's concentrations in the bloodstream: when given as an intramuscular injection, its bioavailability is 90% (as compared to the 100% availability when given directly into a vein), and its highest concentrations in the blood plasma are reached after about 2.3 hours. In the blood, 85–95% of ertapenem are bound to plasma proteins, mostly albumin. Plasma protein binding is higher for lower concentrations, and vice versa. The drug is only partially metabolized, with 94% circulating in form of the parent substance and 6% as metabolites. The main metabolite is the inactive hydrolysis product with the ring opened.

Ertapenem is mainly eliminated via the kidneys and urine (80%) and to a minor extent via the faeces (10%). Of the 80% found in the urine, 38% is excreted as the parent drug and 37% as the ring-opened metabolite. The biological half-life is about 3.5 hours in women, 4.2 hours in men and 2.5 hours in children up to 12 years of age.

Comparison with other antibiotics

Like all carbapenem antibiotics, ertapenem has a broader spectrum of activity than other beta-lactams like penicillins and cephalosporins. Similar to doripenem, meropenem and biapenem, ertapenem has slightly better activity against many Gram-negative bacteria than other carbapenems such as imipenem. In contrast to imipenem, doripenem and meropenem, it is not active against Enterococcus, Pseudomonas and Acinetobacter species.

For diabetic foot infections, ertapenem as a single treatment or in combination with vancomycin has been found to be more effective and have fewer side effects than tigecycline, but in severe cases it is less effective than piperacillin/tazobactam.

Regarding pharmacokinetics, imipenem, doripenem and meropenem have lower plasma protein bindings (up to 25%) and shorter half-lives (about one hour) than ertapenem.

History

Ertapenem is marketed by Merck. It was approved for use by the US Food and Drug Administration in November 2001, and by the European Medicines Agency in April 2002.

References

References

  1. (24 January 2020). "Ertapenem (Invanz) Use During Pregnancy".
  2. (12 August 2022). "INVANZ ertapenem (as sodium) 1g powder for injection vial (81449)".
  3. "TGA eBS - Product and Consumer Medicine Information Licence".
  4. "Invanz 1g powder for concentrate for solution for infusion - Summary of Product Characteristics (SmPC)".
  5. (November 2011). "Carbapenems: past, present, and future". Antimicrobial Agents and Chemotherapy.
  6. (May 2022). "Efficacy of ertapenem, gentamicin, fosfomycin, and ceftriaxone for the treatment of anogenital gonorrhoea (NABOGO): a randomised, non-inferiority trial". The Lancet. Infectious Diseases.
  7. (20 January 2022). "Antibiotic Ertapenem is alternative drug in treatment of gonorrhea".
  8. (13 February 2020). "Invanz- ertapenem sodium injection, powder, lyophilized, for solution".
  9. (29 June 2020). "Ertapenem Sodium Monograph for Professionals". The American Society of Health-System Pharmacists.
  10. (19 November 2019). "Invanz: EPAR – Product Information". [[European Medicines Agency]].
  11. "Ertapenem". mediQ.
  12. (October 2016). "The Effect of Different Carbapenem Antibiotics (Ertapenem, Imipenem/Cilastatin, and Meropenem) on Serum Valproic Acid Concentrations". Therapeutic Drug Monitoring.
  13. (December 2009). "The effect of carbapenem antibiotics on plasma concentrations of valproic acid". The Annals of Pharmacotherapy.
  14. (2019). "Arzneimittel-Interaktionen". Österreichischer Apothekerverlag.
  15. (31 December 2012). "Side Effects of Drugs Annual 34: A worldwide yearly survey of new data in adverse drug reactions". Newnes.
  16. (August 2010). "Decrease in serum valproic acid levels during treatment with ertapenem". American Journal of Health-System Pharmacy.
  17. (June 2023). "StatPearls [Internet].". StatPearls Publishing.
  18. (December 2016). "Morphological and ultrastructural changes in bacterial cells as an indicator of antibacterial mechanism of action". Cellular and Molecular Life Sciences.
  19. (2013). "Arzneimittelwirkungen". Wissenschaftliche Verlagsgesellschaft.
  20. "Ertapenem Ring Open Impurity". U.S. National Library of Medicine.
  21. (September 2015). "Systemic antibiotics for treating diabetic foot infections". The Cochrane Database of Systematic Reviews.
  22. (September 2018). "Antibiotic therapy of diabetic foot infections: A systematic review of randomized controlled trials". Wound Repair and Regeneration.
  23. (20 November 2001). "Drug Approval Package: Invanz I.V. or I.M. (Ertapenem Sodium) NDA #21-337".
  24. (17 September 2018). "Invanz EPAR".
  25. (2 December 2016). "Invanz: EPAR – Summary for the public". [[European Medicines Agency]].

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carbapenem-antibioticsbenzoic-acidsanilidesdrugs-developed-by-merck-&-co.pyrrolidines