Imipenem

Base Information

• Chemical Name: Imipenem
• CAS No.: 64221-86-9
• Deprecated CAS: 127644-14-8,75902-88-4,345631-68-7,345631-68-7
• Molecular Formula: C₁₂H₁₇N₃O₄S
• Molecular Weight: 299.351
• Hs Code.: 29419000
• European Community (EC) Number: 264-734-5,680-398-6
• NSC Number: 759901,717864
• UNII: Q20IM7HE75
• DSSTox Substance ID: DTXSID2023143
• Nikkaji Number: J32.525B
• Wikipedia: Imipenem
• Wikidata: Q425152
• NCI Thesaurus Code: C146984
• RXCUI: 1545986
• Metabolomics Workbench ID: 43585
• ChEMBL ID: CHEMBL148
• Mol file: 64221-86-9.mol

Synonyms:Anhydrous Imipenem;Anhydrous, Imipenem;Imipemide;Imipenem;Imipenem Anhydrous;Imipenem, Anhydrous;MK 0787;MK-0787;MK0787;N Formimidoylthienamycin;N-Formimidoylthienamycin

Chemical Property of Imipenem

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.11E-15mmHg at 25°C
• Melting Point: 106-111 °C
• Refractive Index: 1.721
• Boiling Point: 567.3 °C at 760 mmHg
• PKA: 4.29±0.40(Predicted)
• Flash Point: 296.9 °C
• PSA: 148.25000
• Density: 1.62 g/cm³
• LogP: 0.18820
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Solubility.: Sparingly soluble in water, slightly soluble in methanol.
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 299.09397721
• Heavy Atom Count: 20
• Complexity: 491

Purity/Quality:

99% ^*data from raw suppliers

Imipenem ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
• Isomeric SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
• Recent ClinicalTrials: Imipenem/Cilastatin/Relebactam (IMI/REL) in Treatment of CRE Infections
• Recent EU Clinical Trials: A Phase 3, Multi-Center, Randomized, Single-Blind Study to Assess the Efficacy and Safety of Cefepime/Nacubactam and Aztreonam/Nacubactam Versus Best Available Therapy in Adults With Complicated Urinary Tract Infection, Acute Uncomplicated Pyelonephritis, Hospital-Acquired Bacterial Pneumonia, Ventilator-Associated Bacterial Pneumonia, and Complicated Intra-Abdominal Infection due to Carbapenem-Resistant Enterobacterales
• Recent NIPH Clinical Trials: Embolization using Imipenem(TIENAM) for refractory ulcer which cause is micro AVM
• Description: Imipenem is a chemically stable thienamycin derivative with an antibacterial activity that is broader in spectrum and of greater potency than most of the third generation cephalosporins. Combination with cilastatin, an inhibitor of renal brush-border dehydropeptidase-I, increases both urinary and plasma levels of imipenem.
• Uses: Carbapenem antibacterial.
• Therapeutic Function: Antibiotic
• Clinical Use: Lower respiratory tract infections Urinary tract infections (complicated and uncomplicated) Intra-abdominal infections Gynecological infections Bacterial septicemia Bone and joint infections Skin and skin structure infections Endocarditis Polymicrobial infections

Technology Process of Imipenem

There total 4 articles about Imipenem which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

C22H30N4O6SSi (85737-71-9) → N-formimidoyl thienamycin (64221-86-9,103730-39-8)

Guidance literature:

With hydrogen;

DOI:10.1016/S0040-4039(00)85743-3

Reference yield:

p-nitrobenzyl 6-(1'-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate (74288-40-7,75363-99-4,77171-48-3,77448-91-0,77449-43-5,78184-67-5,111468-09-8,115938-32-4) → N-formimidoyl thienamycin (64221-86-9,103730-39-8)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-diisopropyl ethylamine

2: N,N-diisopropylethylamine or 4-dimethylaminopyridine

3: 63 percent / H₂

With hydrogen; N-ethyl-N,N-diisopropylamine;

DOI:10.1016/S0040-4039(00)85743-3

Reference yield:

(5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (75321-08-3,77171-49-4,77449-44-6) → N-formimidoyl thienamycin (64221-86-9,103730-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-diisopropylethylamine or 4-dimethylaminopyridine

2: 63 percent / H₂

With hydrogen; N-ethyl-N,N-diisopropylamine;

DOI:10.1016/S0040-4039(00)85743-3

upstream raw materials:

N-(N'-p-nitrobenzyloxycarbonyl) formimidoyl cysteamine

(5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

C₂₂H₃₀N₄O₆SSi

p-nitrobenzyl 6-(1'-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate

Refernces