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Imipenem

CAS No.
74431-23-5
Chemical Name:
Imipenem
Synonyms
Imipenem Monohydrate≥ 96% (HPLC);CS-342;MK-0787;Imipenem;lmipemide;EOS-61603;Imipenem(b);Imipenem hydrate;Tienam monohydrate;Imipenem n-Hydrate
CBNumber:
CB8695769
Molecular Formula:
C12H19N3O5S
Molecular Weight:
317.36
MDL Number:
MFCD00864955
MOL File:
74431-23-5.mol
Last updated:2023-09-06 17:45:48

Imipenem 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)
NCI Dictionary of Cancer Terms imipenem
FDA UNII 71OTZ9ZE0A
NCI Drug Dictionary imipenem

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
WGK Germany  3
HS Code  2941906000

Imipenem price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich I0160 Imipenem monohydrate ≥98% (HPLC) 74431-23-5 5mg $137.6 2024-03-01 Buy
Sigma-Aldrich I0160 Imipenem monohydrate ≥98% (HPLC) 74431-23-5 25mg $682 2024-03-01 Buy
Sigma-Aldrich I0090000 Imipenem European Pharmacopoeia (EP) Reference Standard 74431-23-5 I0090000 $153 2024-03-01 Buy
Alfa Aesar J66749 Imipenem monohydrate, 95% 74431-23-5 5mg $97.65 2024-03-01 Buy
Alfa Aesar J66749 Imipenem monohydrate, 95% 74431-23-5 25mg $247 2024-03-01 Buy
Product number Packaging Price Buy
I0160 5mg $137.6 Buy
I0160 25mg $682 Buy
I0090000 I0090000 $153 Buy
J66749 5mg $97.65 Buy
J66749 25mg $247 Buy

Imipenem Chemical Properties,Uses,Production

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 Properties

Off-White Solid

Uses

antidiabetic

Uses

antiulcer

Uses

An extremely broad-spectrum semi-synthetic antibiotic

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.

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.

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Related articles

  • What is Imipenem?
  • Imipenem (N-formimidoylthienamycin monohydrate) is a crystalline derivative of thienamycin, which is produced by Streptomyces ....
  • Feb 19,2020

View Lastest Price from Imipenem manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
imipenem hydrate pictures 2024-03-20 imipenem hydrate
74431-23-5
US $10.00 / g 1g 98%+ 20KG Wuhan Topule Biopharmaceutical Co., Ltd
Imipenem pictures 2023-09-06 Imipenem
74431-23-5
US $40.00-40.00 / kg 1kg 0.99 10 tons Hebei Yanxi Chemical Co., Ltd.
Imipenem pictures 2023-03-29 Imipenem
74431-23-5
US $60.00-50.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biotechnology Co., Ltd.
  • imipenem hydrate pictures
  • imipenem hydrate
    74431-23-5
  • US $10.00 / g
  • 98%+
  • Wuhan Topule Biopharmaceutical Co., Ltd
  • Imipenem pictures
  • Imipenem
    74431-23-5
  • US $40.00-40.00 / kg
  • 0.99
  • Hebei Yanxi Chemical Co., Ltd.
  • Imipenem pictures
  • Imipenem
    74431-23-5
  • US $60.00-50.00 / KG
  • 99%
  • Hebei Lingding Biotechnology Co., Ltd.

Imipenem Spectrum

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 Tienam monohydrate Imipenem monohydrate, >=98% Imipenem Monohydrate, Antibiotic for Culture Media Use Only (6 R,7 R)-7-AMIMO-8-OXO-3-(1-PROPENYL)-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID 5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID, 7-AMINO-8-OXO-3-(1-PROPENYL)-, (6R,7R)- (6 R ,7 R ) - 7-AMIMO-8-OXO-3-(1-PROPENYL)-5-THIA-1-AZABICYLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID (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 lmipemide MK-0787 (5R,6S)-3-((2-Formimidamidoethyl)thio)-6-((R)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.]hept-2-ene-2-carboxylic acid hydrate [5R-[5α,6α(R^<*>^)]]-6-(1-hydroxyethyl)-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate Imipenem n-Hydrate CS-342 EOS-61603 IMIPEMIDE MONOHYDRATE N-Formimidoyl thienamycin monohydrate Imipenem USP/EP/BP Imipenem monohydrate (High purity) Imipenem 1-hydrate ?mipenem monohydrate Crude (6R,7R)-7-AMIMO-8-OXO-3-(1-PROPENYL)-5-THIA-1-azabicyclo[4.2... Imipenem MonohydrateQ: What is Imipenem Monohydrate Q: What is the CAS Number of Imipenem Monohydrate Q: What is the storage condition of Imipenem Monohydrate Imipenem crude(monohydrate non sterile) Imipenem crude(monohydrate non sterile) Imipenem Monohydrate (1337809) Imipenem Monohydrate≥ 96% (HPLC) bacteria,Inhibitor,N-Formimidoyl thienamycin,P. aeruginosa,ntibiotic,MK0787,Imipenem monohydrate,MK 0787,MK-0787,infection,inhibit,Bacterial,Antibiotic,thienamycin Imipenem(b) 74431-23-5 C12H17N3O4SH2O ROXIT Intermediates & Fine Chemicals Pharmaceuticals