Structure via PubChem · Public domain (PubChem)
ertapenem
Sign in to saveAlso known as (4R,5S,6S)-3-((3S,5S)-5-((3-Carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid, (1R,5S,6S,8R,2'S,4's)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid
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.
Key facts
- Drug.H
- 25
- Drug.N
- 3
- Drug.O
- 7
- Drug.S
- 1
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 461095141
- Drug.image
- Ertapenem skeletal structure.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Ertapenem ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Invanz
- Drug.MedlinePlus
- a614001
- Drug.DailyMedID
- Ertapenem
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- Intramuscular, intravenous
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- DH03
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C22H25N3O7S
- Molecular weight
- 475.5 g/mol
- IUPAC name
- (4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
- SMILES
- C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)[C@@H](C)O
- InChIKey
- JUZNIMUFDBIJCM-ANEDZVCMSA-N
- XLogP
- -1.5
- Polar surface area
- 182 Ų
- H-bond donors
- 5
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Research
2,591 papers- Cefazolin and Ertapenem Salvage Therapy Rapidly Clears Persistent Methicillin-Susceptible Staphylococcus aureus Bacteremia.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2020
- Ertapenem in the Context of Hypoalbuminemia: Implications for Critically Ill Patients.Journal of clinical pharmacology · 2025
- Ertapenem.Kathmandu University medical journal (KUMJ) · 2009
- Ertapenem.Expert opinion on pharmacotherapy · 2010
- [Ertapenem].Revista espanola de quimioterapia : publicacion oficial de la Sociedad Espanola de Quimioterapia · 2007
via PubMed
Wikidata facts
- Subclass of
- carbapenem antibiotic
- Mass
- 475.141321
- Manufacturer
- Pfizer
- Has use
- medication
Show 9 more facts
- medical condition treated
- pyelonephritis
- chemical formula
- C₂₂H₂₅N₃O₇S
- isomeric SMILES
- C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)[C@@H](C)O
- canonical SMILES
- CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)NC4=CC=CC(=C4)C(=O)O)C(=O)O)C(C)O
- World Health Organisation international non-proprietary name
- ertapenem
- defined daily dose
- 1
- subject has role
- bactericide
- stylized name
- INVanz
- Commons category
- Ertapenem
Sources (7)
via Wikidata · CC0
~8 min read
Encyclopedic overview
13 sectionsContents
- Medical uses
- Contraindications
- Side effects
- Overdose
- Interactions
- Pharmacology
- Mechanism of action
- Susceptible bacteria
- Resistance
- Pharmacokinetics
- Comparison with other antibiotics
- History
- References
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.
Excerpted from Wikipedia’s “ertapenem” article, available under the CC BY-SA 4.0 licence.