Structure via PubChem · Public domain (PubChem)
imipen
Sign in to saveAlso known as IMP, (5R,6S)-3-(2-Formimidoylamino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid, N-formimidoylthienamycin, Imipenem anhydrous, (5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure, Imipemide, Imipenem, n-formimidoyl thienamycin, (5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
Imipenem, sold under the brand name Primaxin among others, is a synthetic β-lactam antibiotic belonging to the carbapenems chemical class. developed by Merck scientists Burton Christensen, William Leanza, and Kenneth Wildonger in the mid-1970s. Carbapenems are highly resistant to the β-lactamase enzymes produced by many multiple drug-resistant Gram-negative bacteria, thus playing a key role in the treatment of infections not readily treated with other antibiotics. It is usually administered through intravenous injection.
Chemical data
- Formula
- C12H17N3O4S
- Molecular weight
- 299.35 g/mol
- IUPAC name
- (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
- SMILES
- C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
- InChIKey
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N
- XLogP
- -0.7
- Polar surface area
- 142 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 299.093977
Show 4 more facts
- chemical formula
- C₁₂H₁₇N₃O₄S
- isomeric SMILES
- C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
- canonical SMILES
- CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
- Commons category
- Imipenem
via Wikidata · CC0
~4 min read
Article
6 sectionsContents
- Medical uses
- Spectrum of bacterial susceptibility and resistance
- Coadministration with cilastatin
- Adverse effects
- References
- Further reading
{{Drugbox | verifiedrevid = 443870020 | IUPAC_name = (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-({2-[(iminomethyl)amino]ethyl}thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid | image = Imipenem.svg | image_class = skin-invert-image | image2 = Imipenem ball-and-stick model from xtal 2020.png | image_class2 = bg-transparent
| tradename = Primaxin, others | Drugs.com = | MedlinePlus = a686013 | DailyMedID = Imipenem | pregnancy_AU = B3 | legal_AU = S4 | legal_CA = Rx-only | legal_UK = POM | legal_US = Rx-only | routes_of_administration = Intramuscular, intravenous | ATC_prefix = J01 | ATC_suffix = DH51