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HomeProduct name listImipenem

Imipenem

Synonym(s):(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 monohydrate;Imipenem monohydrate;Primaxin monohydrate;Tienam monohydrate

  • CAS NO.:74431-23-5
  • Empirical Formula: C12H19N3O5S
  • Molecular Weight: 317.36
  • MDL number: MFCD00864955
  • EINECS: 680-398-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 21:04:56
Imipenem Structural

What is Imipenem?

Chemical properties

Off-White Solid

The Uses of Imipenem

Imipenem has a broad spectrum of antimicrobial action, which includes most clinically significant microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is resistant with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria. It is used for bacterial infections of the lower respiratory tract, infections of the urinary and sexual tracts, infections of bones, joints, skin, soft tissues, intraabdominal and gynecological infections, bacterial septicemia, and endocarditis.
Imipenem undergoes enzymatic inactivation in the kidneys. In order to avoid this problem, it is used in a 1:1 ratio in combination with cilastatin—the sodium salt of [R-[R,S-(Z)]]-7-[(2- amino-2-carboxyethyl)thio]-2-[[(2,2-dimethylcyclopropyl)aminocarbonyl-2-heptenoic acid (32.1.3.6), which inhibits metabolisms of imipenem in the kidneys. This combination of two compounds is also used in medicine under the name primaxin.

The Uses of Imipenem

An extremely broad-spectrum semi-synthetic antibiotic

The Uses of Imipenem

antiulcer

The Uses of Imipenem

antidiabetic

Definition

ChEBI: Imipenem hydrate is a member of carbapenems. It contains an imipenem.

General Description

Chemical structure: ?-lactam

Biochem/physiol Actions

Imipenem is found effective against gram positive and negative aerobes and anaerobes. Imipenem is often combined with cilastatin, to inhibit its metabolism in kidney.

Synthesis

Imipenem, [5R-[5|á,6|á(R)]]-6-(1-hydroxyethyl)-3-[[2-[(iminomethyl)amino] ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-2-carboxylic acid (32.1.3.1), is the only carbapenem presently used in clinics. It is synthesized from thienamycin isolated from Streptomyces cattleya by reacting it with the methyl formimidate.

Synthesis_74431-23-5


Unlike penicillins and cephalosporins, which have a side aminoacyl group joined to the betalactam ring, imipenem has a |á-hydroxyethyl side chain. Significant resistance to hydrolysis by beta-lactamases is observed in this compound, evidently thanks to the trans-configuration of the side chain, while the side chain of penicillins and cephalosporins have a cis configuration.

Properties of Imipenem

Melting point: 193-198°C
Boiling point: 567℃
RTECS  CL5446516
Flash point: >110°(230°F)
storage temp.  Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility  H2O: >5mg/mL
form  powder
pka pKa 3.2/9.9(H2O,t = 25) (Uncertain)
color  white to beige
Water Solubility  Soluble in water at 5mg/ml
CAS DataBase Reference 74431-23-5(CAS DataBase Reference)

Safety information for Imipenem

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for Imipenem

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