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Imipenem

HCID 104838
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
64221-86-9
Standard-SMILES
C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(SCCN=CN)C[C@H]12
InChIKey
ZSKVGTPCRGIANV-ZXFLCMHBSA-N
Summenformel
C12H17N3O4S
Durchschnittliche Molmasse
299,35 g/mol
Monoisotopische Masse
299,09397721

Überblick

Imipenem is a broad-spectrum, intravenous beta-lactam antibiotic of the carbapenem subgroup. It has a role as an antibacterial drug. It is a member of carbapenems and a beta-lactam antibiotic allergen. It is a tautomer of an imipenem zwitterion.

Namen und Bezeichner

Bevorzugter Name
Imipenem
IUPAC
(5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Lokaler Name
Imipenem
Englischer Name
Imipenem
Summenformel
C12H17N3O4S
Molmasse
299.35

Namen und Synonyme

imipenem64221-86-9ImipemideImipenem anhydrousN-FormimidoylthienamycinImipenemumN-formimidoyl thienamycinAnhydrous Imipenem(5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidMK 0787DTXSID2023143CHEBI:471744
Weitere Namen anzeigen
imipenamImipenenLMipeneMImipenem CRS(5R)-6β-[(R)-1-Hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid(5R,6S)-3-({2-[(E)-(aMinoMethylidene)aMino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidmk-787EOS-62374
Imipenem, AnhydrousMK-0787Q20IM7HE75(5R,6S)-6-((R)-1-Hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure(5R,6S)-3-((2-(Formimidoylamino)ethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acidDTXCID903143Imipenem monohydrate (h2o)RECARBRIO COMPONENT IMIPENEM

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,7
Polarare Oberfläche (TPSA)
142 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
6
Schwere Atome
20
Formalladung
0
Komplexität
491

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics

Solubility7.76e-01 g/L
Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid
Dissociation Constants3.2
Collision Cross Section169.26 Ų [M+H]+

Physikochemische Eigenschaften

Schmelzpunkt
106 · 106-111 C
Siedepunkt
530.2 · 530.2±60.0 °C(Predicted)
Dichte
1.62 · 1.62±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Exposure RoutesImipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally.
Toxicity Summary · 1 Eintrag

Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria. This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to pencillin binding proteins (PBPs). In E. coli and selected strains of P. aeruginosa, imipenem has shown to have the highest affinity to PBP-2, PBP-1a, and PBP-1b. This preferential binding to PBP-2 and PBP-1b results in the direct conversion of the individual cell to a spheroblast, which leads to rapid cell lysis and death without filament formation.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Imipenem

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Sicherheitsdaten

wgk
WGK 3
hs_code
29419000
risk_code
36/37/38
hazard_code
Xi
safety_code
26-27-36/37/39
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

ATC CodeJ01DH51
Protein BindingImipenem is 20% bound to plasma proteins.
Pharmacodynamics · 1 Eintrag

Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. Imipenem is active against aerobic and anaerobic Gram positive as well as Gram negative bacteria including <i>Pseudomonas aeruginosa</i> and the <i>Enterococcus</i>. It exerts a bactericidal effects by disrupting cell wall synthesis.

Mechanism of Action · 1 Eintrag

Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria. This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to penicillin-binding proteins (PBPs). In E. coli and selected strains of P. aeruginosa, imipenem has shown to have the highest affinity to PBP-2, PBP-1a, and PBP-1b. This inhibition of PBPs prevents the bacterial cell from adding to the peptidoglycan polymer which forms the bacterial cell wall eventually leading to cell death.

Biological Half-LifeWhen given via IV injection imipenem has a half-life of 1 h. The apparent half-life of the IM injection ranges from 1.3-5.1 h, likely due to slower absorption form the injection site.
Metabolism/Metabolites · 2 Einträge

Imipenem is metabolized by renal dehydropeptidase.

Renal. Half Life: 1 hour

FDA Pharmacological Classification · 5 Einträge

Q20IM7HE75

IMIPENEM ANHYDROUS

Chemical Structure [CS] - Carbapenems

Established Pharmacologic Class [EPC] - Penem Antibacterial

Imipenem anhydrous is a Penem Antibacterial.

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.

Zugehörige Reaktionen

2
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 224412
HRID 224412als Produktuspto-grants-1980_11
Reaktionsgleichung von HRID 1156231
HRID 1156231als Produktuspto-grants-1982_06

Notizen zur Verbindung

Wird geladen…

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Datenbank-Bezeichner

CAS
64221-86-9、74431-23-5
PubChem CID
104838
DTXSID
DTXSID2023143
ChEMBL
CHEMBL148、CHEMBL43708
ChEBI
CHEBI:471744
UNII
Q20IM7HE75
EC Number
264-734-5
Nikkaji
J32.525B
Löslichkeit
Sparingly soluble in water, slightly soluble in methanol.
Aggregatzustand
Solid
pka
4.29 · 4.29±0.40(Predicted)
Farbe
Off-white to yellow
Major Application
pharmaceutical (small molecule)
InChI
InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
InChIKey
ZSKVGTPCRGIANV-ZXFLCMHBSA-N
SMILES
N12[C@@]([H])([C@@H]([C@H](O)C)C1=O)CC(SCCNC=N)=C2C(O)=O
CAS Datenbank
64221 · 64221-86-9(CAS DataBase Reference)
EPA chemische Informationen
Imipenem (64221-86-9)
Absorption, Distribution and Excretion · 4 Einträge

Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally. The bioavailability of the IM injection is 89%.

Approximately 70% of imipenem is excreted in the urine as the parent drug.

The reported volume of distribution for imipenem ranges from 0.23-0.31 L/kg.

The total clearance of imipenem is 0.2 L/h/kg. When used alone, the renal clearance is 0.05 L/h/kg. In combination with cilastatin the renal clearance of imipenem is 0.15 L/h/kg, likely due to the increased concentration of the parent drug.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 2 Einträge

Use (kg) in Switzerland (2009): >100

For the treatment of bacterial infections caused by susceptible bacteria.

Anwendungen · 2 Einträge

BeschreibungImipenem is a chemically stable thienamycin derivative with an antibacterial activity that is broader in spectrum and of greater potency than most of the third generation cephalosporins. Combination with cilastatin, an inhibitor of renal brush-border dehydropeptidase-I, increases both urinary and plasma levels of imipenem.

VerwendenCarbapenem antibacterial.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Thienamycin

Anbieter100 Anbieter

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