Ertapenem
Systematic (IUPAC) name
3-[5-[(3-carboxyphenyl) carbamoyl]pyrrolidin-3-yl] sulfanyl-7-(1-hydroxyethyl)- 2-methyl- 6-oxo-5-azabicyclo[3.2.0] hept-3-ene-4-carboxylic acid
Identifiers
CAS number	153832-46-3
ATC code	J01DH03
PubChem	150610
DrugBank	APRD00952
Chemical data
Formula	C22H25N3O7S
Mol. mass	475.516 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	? Image File history File links This is a lossless scalable vector image. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article or section does not cite any references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Standard atomic weight 32. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Legal status
Routes	?

Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz®. It is structurally very similar to meropenem in that it possess a 1-β-methyl group. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Carbapenems are a class of beta-lactam antibiotics. ... Staphylococcus aureus - Antibiotics test plate. ... It has been suggested that Rosetta Biosoftware be merged into this article or section. ... Meropenem is an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections, including meningitis and pneumonia. ...

Indications

Ertapenem has been designed to be effective against Gram negative bacteria. It is not active against MRSA, ampicillin-resistant enterococci, Pseudomonas aeruginosa or Acinetobacter species. Ertapenem also has clinically useful activity against anaerobic bacteria. Gram-negative bacteria are those that retain crystal violet dye in the Gram staining protocol. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... MRSA, or methicillin-resistant Staphylococcus aureus, is a bacterium that has developed antibiotic resistance, first to penicillin in 1947, and later to methicillin. ... Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. ... Species E. faecalis etc. ... Binomial name Pseudomonas aeruginosa (Schroeter 1872) Migula 1900 Synonyms Bacterium aeruginosum Schroeter 1872 Bacterium aeruginosum Cohn 1872 Micrococcus pyocyaneus Zopf 1884 Bacillus aeruginosus (Schroeter 1872) Trevisan 1885 Bacillus pyocyaneus (Zopf 1884) Flügge 1886 Pseudomonas pyocyanea (Zopf 1884) Migula 1895 Bacterium pyocyaneum (Zopf 1884) Lehmann and Neumann 1896 Pseudomonas polycolor... Species A. baumannii A. lwoffii etc. ... An anaerobic organism or anaerobe is any organism that does not require oxygen. ...

Ertapenem is marketed by Merck as a first-line treatment for community-acquired infections. It should not be used as empirical treatment for hospital-acquired infections because of its lack of activity against Pseudomonas aeruginosa. In practice, it is reserved primarily for use against ESBL-producing and high level AmpC-producing Gram-negative bacteria. Beta-lactamase is a type of enzyme (EC 3. ...

Dosage

Ertapenem is dosed as 1g given by intravenous injection over 30 minutes, or 1g diluted with 3.2ml of 1% lidocaine given intramuscularly. There is no oral preparation of ertapenem available. Ertapenem cannot be mixed with glucose. An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Lidocaine (INN) (IPA: ) or lignocaine (former BAN) (IPA: ) is a common local anesthetic and antiarrhythmic drug. ... Intramuscular injection is an injection of a substance directly into a muscle. ...

The marketing slogan for ertapenem is "The Power of One", because the dose is one gram, once a day. Look up slogan in Wiktionary, the free dictionary. ... BIC pen cap, about 1 gram. ...

Pharmacology

Unlike imipenem and meropenem, ertapenem is highly protein bound, which explains its long half life (4 hours). Imipenem is an intravenous beta-lactam antibiotic developed in 1985. ... Meropenem is an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections, including meningitis and pneumonia. ...

Ertapenem is excreted primarily (80%) by the kidneys. Metabolism by the liver is not clinically important and does not affect dosing. Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ...

Patients on haemodialysis should be given ertapenem at least 6 hours before dialysis. If it is given less than six hours before dialysis, then the patient should be given an additional dose of 150mg IV after dialysis. Ideally, patients on haemodialysis should be given ertapenem immediately following dialysis. In medicine, dialysis is a method for removing waste such as urea from the blood when the kidneys are incapable of this, i. ...

Resistance

Acquired resistance to ertapenem is usually mediated by up-regulation of efflux mechanisms and by the selection of porin-deficient mutants. Organisms that produce a metallo-β-lactamase are innately immune to ertapenem (as well as all carbapenems) (Reference needed). Beta-lactamase is a type of enzyme (EC 3. ... Carbapenems are a class of beta-lactam antibiotics. ...

Side effects

There are few adverse effects of ertapenem. The only absolute contra-indication is a previous anaphylactic reaction to ertapenem or other β-lactam antibiotic. There are no studies done in pregnant women, so the manufacturers cannot comment on its safety in pregnancy. In 2006, Ertapenem is now approved for pediatric use in certain infections. Ertapenem is not recommended for children under 3 months of age and children with meningitis. An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Anaphylaxis is an acute systemic (multi-system) and severe Type I Hypersensitivity allergic reaction. ...

Use of all antibiotics is associated with increased rates of resistance (although carbapenem resistance is currently rare). There is particular worry that although ertapenem has no clinically useful activity against Pseudomonas aeruginosa, widespread use of ertapenem could still lead to increased carbapenem resistance in Pseudomonas (Livermore et al. 2005). Antibiotic resistance is the ability of a micro-organism to withstand the effects of an antibiotic. ... Binomial name Pseudomonas aeruginosa (Schroeter 1872) Migula 1900 Synonyms Bacterium aeruginosum Schroeter 1872 Bacterium aeruginosum Cohn 1872 Micrococcus pyocyaneus Zopf 1884 Bacillus aeruginosus (Schroeter 1872) Trevisan 1885 Bacillus pyocyaneus (Zopf 1884) Flügge 1886 Pseudomonas pyocyanea (Zopf 1884) Migula 1895 Bacterium pyocyaneum (Zopf 1884) Lehmann and Neumann 1896 Pseudomonas polycolor...

Like many antibiotics, Clostridium difficile colitis has been associated with its use. Binomial name Clostridium difficile Hall & OToole, 1935 Clostridium difficile or CDF/cdf (Template:Audo, alternatively ) (also referred to as C. diff or C-diff) is a species of bacteria of the genus Clostridium which are gram-positive, anaerobic, spore-forming rods (bacillus). ... Pseudomembranous colitis is an infection of the colon often, but not always, caused by the bacterium Clostridium difficile. ...

References

• Livermore DM, Mushtaq S, Warner M (2005). "Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems". J Antimicrob Chemother 55 (3): 306–311.