Imipenem Chemical Properties

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

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

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

Broad-spectrum antibiotic

Chemical Properties

Off-White Solid

Uses

antiulcer

Uses

antidiabetic

Uses

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.

Uses

An extremely broad-spectrum semi-synthetic antibiotic

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.

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.

Imipenem(74431-23-5)Related Product Information

• (5R,6S)-3-[(Diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
• Ethylparaben
• Ethylbenzene
• 2-(METHYLSULFONYL)ETHANOL
• Ethyl propionate
• Ethyl formate
• Ethyl acetate
• EC 2.6.1.2
• INTERMEDIANTE FOR IMIPENEM
• Ethyl acrylate
• Acetaminophen
• Sulfamic acid
• IMIPEMIDE IMIPENEM IMIPENEN N-FORMIMIDOYLTHIENAMYCIN TIENAMYCIN,Imipenem
• Glucosamine
• Ethanol
• Imipenem Impurity 3
• Imipenem Impurity 4
• Imipenem EP Impurity B