Chemical Properties Discovery Broad-spectrum antibiotic
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Imipenem

Chemical Properties Discovery Broad-spectrum antibiotic
Product Name
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
Formula Weight
317.36
MOL File
74431-23-5.mol
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Imipenem Property

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)
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Safety

WGK Germany 
3
HS Code 
2941906000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
I0160
Product name
Imipenem monohydrate
Purity
≥98% (HPLC)
Packaging
5mg
Price
$137.6
Updated
2024/03/01
Sigma-Aldrich
Product number
I0160
Product name
Imipenem monohydrate
Purity
≥98% (HPLC)
Packaging
25mg
Price
$682
Updated
2024/03/01
Sigma-Aldrich
Product number
I0090000
Product name
Imipenem
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
I0090000
Price
$153
Updated
2024/03/01
Alfa Aesar
Product number
J66749
Product name
Imipenem monohydrate, 95%
Packaging
5mg
Price
$97.65
Updated
2024/03/01
Alfa Aesar
Product number
J66749
Product name
Imipenem monohydrate, 95%
Packaging
25mg
Price
$247
Updated
2024/03/01
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Imipenem Chemical Properties,Usage,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

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 Preparation Products And Raw materials

Raw materials

Silica glass 6-Aminopenicillanic acid INSTANT BUFFER S70, PH7.0 (ACC. TO SOERENSEN)(50PACKS) Trimethacrylate Benzyl ester N,N-Dimethylformamide Sodium bisulfite water solution MERCURIC ACETATE Sodium nitrite Tetrahydrofuran Ammonium chloride VINYLACETIC ACID Acetic acid Ammonium acetate Iodomethane

Preparation Products

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View Lastest Price from Imipenem manufacturers

Apeloa production Co.,Limited
Product
Imipenem 74431-23-5
Price
US $1.00/g
Min. Order
1g
Purity
0.98
Supply Ability
1000
Release date
2024-05-29
Shaanxi Dideu Medichem Co. Ltd
Product
Imipenem 74431-23-5
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-07
Hebei Yanxi Chemical Co., Ltd.
Product
Imipenem 74431-23-5
Price
US $40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-09-06

74431-23-5, ImipenemRelated Search:

(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

  • 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
  • Tienam monohydrate
  • Imipenem monohydrate, >=98%
  • Imipenem Monohydrate, Antibiotic for Culture Media Use Only
  • Imipenem n-Hydrate
  • CS-342
  • (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
  • EOS-61603
  • IMIPEMIDE MONOHYDRATE
  • [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
  • 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)
  • bacteria,Inhibitor,N-Formimidoyl thienamycin,P. aeruginosa,ntibiotic,MK0787,Imipenem monohydrate,MK 0787,MK-0787,infection,inhibit,Bacterial,Antibiotic,thienamycin
  • Imipenem（b）
  • lmipenem monohydrate
  • 74431-23-5
  • C12H17N3O4SH2O
  • ROXIT
  • Intermediates & Fine Chemicals
  • Pharmaceuticals