Basic information Chemical Properties Discovery Broad-spectrum antibiotic Safety Related Supplier
ChemicalBook >  Product Catalog >  API >  Antibiotics >  β-Lactamase inhibitors >  Imipenem

Imipenem

Basic information Chemical Properties Discovery Broad-spectrum antibiotic Safety Related Supplier
Imipenem Basic information
Imipenem Chemical Properties
  • Melting point:193-198°C
  • Boiling point:567℃
  • RTECS CL5446516
  • Flash point:>110°(230°F)
  • storage temp. -20°C Freezer
  • solubility H2O: >5mg/mL
  • pkapKa 3.2/9.9(H2O,t = 25) (Uncertain)
  • form powder
  • color white to beige
  • Water Solubility Soluble in water at 5mg/ml
  • CAS DataBase Reference74431-23-5(CAS DataBase Reference)
Safety Information
  • WGK Germany 3
  • HS Code 2941906000
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).
  • Chemical PropertiesOff-White Solid
  • Usesantiulcer
  • Usesantidiabetic
  • UsesImipenem 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.
  • UsesAn extremely broad-spectrum semi-synthetic antibiotic
  • Chemical SynthesisImipenem, [5R-[5α,6α(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.


    Unlike penicillins and cephalosporins, which have a side aminoacyl group joined to the betalactam ring, imipenem has a α-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.
Imipenem Preparation Products And Raw materials
Imipenem(74431-23-5)Related Product Information
ImipenemSupplierMore
  • Company Name:Jinan Yaoyan Pharmaceutical Co., Ltd. Gold
  • Tel:
  • Email:jnyaoyan@163.com
  •  
  • Company Name:ShangHai Biochempartner Co.,Ltd Gold
  • Tel:15971444841 159-71444841-
  • Email:amber@biochempartner.com
  •  
  • Company Name:SHANDONG OCTAGON CHEMICALS LIMITED Gold
  • Tel:15589503653
  • Email:sales@octagonchem.com;ella@octagonchem.com
  •  
  • Company Name:Wuhan Topule Gold
  • Tel:19945035818 027-8721-5551
  • Email:2936752263@qq.com;2838271459@qq.com
  •  
  • Company Name:J & K SCIENTIFIC LTD.
  • Tel:400-666-7788 010-82848833-
  • Email:jkinfo@jkchemical.com;market6@jkchemical.com
  •  
Related articles