Ertapenem

Ertapenem

Clinical data
Trade names	Invanz
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B3 US: B (No risk in non-human studies)
Routes of administration	Intramuscular, intravenous
ATC code	J01DH03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	90% (intramuscular)
Protein binding	Inversely proportional to concentration; 85 to 95%
Metabolism	Minor hydrolysis of beta-lactam ring, not involved
Biological half-life	4 hours
Excretion	Renal (80%) and fecal (10%)
Identifiers
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
CAS Number	153832-46-3 Y
PubChem CID	150610
DrugBank	DB00303 Y
ChemSpider	132758 Y
UNII	G32F6EID2H
KEGG	D04049 N
ChEBI	CHEBI:404903 Y
ChEMBL	CHEMBL1359 Y
Chemical and physical data
Formula	C22H25N3O7S
Molar mass	475.516 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)c1cc(ccc1)NC(=O)[C@H]4NC[C@@H](S\C3=C(\N2C(=O)[C@H]([C@H](O)C)[C@H]2[C@H]3C)C(=O)O)C4
InChI InChI=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 Y Key:JUZNIMUFDBIJCM-ANEDZVCMSA-N Y
NY (what is this?)

Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz. It is structurally very similar to meropenem in that it possesses a 1-β-methyl group. Other members of the carbapenem group (imipenem, doripenem, and meropenem) are broadly active antibacterials that are used for infections caused by difficult to treat or multidrug-resistant bacteria (such as ESBL expressing Klebsiella pneumonia). They have very short serum half-lives and must be administered by intravenous infusion every 6 to 8 hours. Ertapenem differs from other carbapenems in having a somewhat less broad spectrum of activity (not against Pseudomonas aeruginosa), and in that its extended serum half-life allows it to be administered once every 24 hours.

Ertapenem has been designed to be effective against Gram-negative and Gram-positive bacteria. It is not active against MRSA, ampicillin-resistant enterococci, Pseudomonas aeruginosa, or Acinetobacter species. Ertapenem also has clinically useful activity against anaerobic bacteria.

Ertapenem has been shown to be active against most isolates of the following micro-organisms in vitro and in clinical infections.

Aerobic and facultative gram-positive microorganisms: Staphylococcus aureus (methicillin-susceptible isolates only), Streptococcus agalactiae, Streptococcus pneumoniae (penicillin-susceptible isolates only), Streptococcus pyogenes,

Note: Methicillin-resistant staphylococci and Enterococcus spp. are resistant to ertapenem.