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ایمی‌پنم

Structure via PubChem · Public domain (PubChem)

EntityQ425152· pop 23· linked from 235 articles

ایمی‌پنم

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Also 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

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
First approval
1985
Admin. routes
parenteral

via ChEMBL · EBI

Wikidata facts

Mass
299.093977
Has use
medication
Show 7 more facts
chemical formula
C₁₂H₁₇N₃O₄S
medical condition treated
staphylococcal infection
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
found in taxon
Nostoc
subject has role
bactericide
Sources (3)

via Wikidata · CC0