Ertapenem

Ertapenem
Clinical data
Trade names	Invanz
AHFS/Drugs.com	Monograph
MedlinePlus	a614001
License data	EU EMA: by INN; US DailyMed: Ertapenem;
Pregnancy; category	AU: B3;
Routes of; administration	Intramuscular, intravenous
ATC code	J01DH03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	90% (intramuscular)
Protein binding	Inversely proportional to concentration; 85 to 95%
Metabolism	Hydrolysis of beta-lactam ring, CYP not involved
Elimination half-life	4 hours
Excretion	Kidney (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 ;
PubChem CID	150610;
DrugBank	DB00303 ;
ChemSpider	132758 ;
UNII	G32F6EID2H;
KEGG	D04049 ;
ChEBI	CHEBI:404903 ;
ChEMBL	ChEMBL1359 ;
CompTox Dashboard (EPA)	DTXSID50165456 ;
Chemical and physical data
Formula	C22H25N3O7S
Molar mass	475.52 g·mol−1
3D model (JSmol)	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 ; Key:JUZNIMUFDBIJCM-ANEDZVCMSA-N ;
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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 (feeling sick), 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.

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