Imipenem CAS NO.74431-23-5

Product Name:    Imipenem
Synonyms:    Imipenem Monohydrate≥ 96% (HPLC);Imipenem hydrate;Imipenem Monohydrate (100 mg);Crude Grade of Imipenem;(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, Primaxin monohydrate, Tienam monohydrate;(6 R,7 R)-7-AMIMO-8-OXO-3-(1-PROPENYL)-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID Monohydrate;(5R,6S)-3-((2-Formimidamidoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate;Primaxin monohydrate
CAS:    74431-23-5
MF:    C12H19N3O5S
MW:    317.36
EINECS:    680-398-6
Product Categories:    ROXIT;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:    74431-23-5.mol
 

Melting point     193-198°C
Boiling point     567℃
RTECS     CL5446516
Fp     >110°(230°F)
storage temp.     Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility     H2O: >5mg/mL
pka    pKa 3.2/9.9(H2O,t = 25) (Uncertain)
form     powder
color     white to beige
Water Solubility     Soluble in water at 5mg/ml
CAS DataBase Reference    74431-23-5(CAS DataBase Reference)
Safety Information
WGK Germany     3
HS Code     2941906000
MSDS Information
Imipenem Usage And Synthesis
Chemical Properties    
Imipenem (N-formimidoylthienamycin monohydrate) is a crystalline derivative of thienamycin, which is produced by Streptomyces cattleya. Its chemical name is (5 R,6S)-3-[[2-(formimidoylamino)ethyl]thio]-6-[( R)-1-hydroxyethyl ]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate. It is an off-white, nonhygroscopic crystalline compound with a molecular weight of 317.37. It is sparingly soluble in water and slightly soluble in methanol.

Discovery    
Imipenem is an intravenous β-lactam antibiotic discovered by Merck scientists Burton Christensen, William Leanza, and Kenneth Wildonger in the mid-1970s. Imipenem was patented in 1975 and approved for medical use in 1985.
Imipenem has a broad spectrum of activity against aerobic and anaerobic, Gram-positive and Gram-negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. It is not active against MRSA, however.
Broad-spectrum antibiotic    
Imipenem is a semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains.It is stable to many beta-lactamases. Similar compounds include meropenem, known for having greater activity against Gram negative bacteria, and the newer ertapenem which exhibits a longer half-life due to increased binding to plasma proteins.
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).