Panipenem

Base Information

• Chemical Name: Panipenem
• CAS No.: 87726-17-8
• Deprecated CAS: 98167-70-5
• Molecular Formula: C15H21N3O4S
• Molecular Weight: 339.415
• European Community (EC) Number: 841-739-6
• UNII: W9769W09JF
• DSSTox Substance ID: DTXSID20868982
• Nikkaji Number: J431.985K
• Wikipedia: Panipenem
• Wikidata: Q7131192
• NCI Thesaurus Code: C66303
• ChEMBL ID: CHEMBL339323
• Mol file: 87726-17-8.mol

Synonyms:6-(1-hydroxyethyl)-2-(1--acetimidoylpyrrolidin-3-ylthio)-1-carbapen-2-em-3-carboxylic acid;carbapenem RS 533;carbapenem RS-533;CS 533;CS-533;panipenem

Chemical Property of Panipenem

Chemical Property:

• Vapor Pressure: 1.18E-14mmHg at 25°C
• Melting Point: 198-200° (dec)
• Refractive Index: 1.745
• Boiling Point: 555.5 °C at 760 mmHg
• Flash Point: 289.7 °C
• PSA: 130.23000
• Density: 1.62 g/cm³
• LogP: 0.67430
• Storage Temp.: Amber Vial, Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Very Slightly), Water (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 339.12527733
• Heavy Atom Count: 23
• Complexity: 606

Purity/Quality:

99% ^*data from raw suppliers

Panipenem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2CC(=C(N2C1=O)C(=O)O)SC3CCN(C3)C(=N)C)O
• Isomeric SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)S[C@H]3CCN(C3)C(=N)C)O
• Uses: Panipenem is a broad spectrum carbapenem antibacterial and antimicrobial agent working against Gram-negative and Gram-positive organisms.

Technology Process of Panipenem

There total 2 articles about Panipenem 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: 89.4%

2-oxo-2H-azepine + ethyl acetimidate hydrochloride (2208-07-3) + 4-nitrobenzyl 2-diazo-3-oxo-butanoate (82551-63-1) + 3-(S)-acetylthio-1-p-nitrobenzyloxycarbonylpyrrolidine (91319-84-5) → panipenem (87726-17-8)

Guidance literature:

2-oxo-2H-azepine; 4-nitrobenzyl 2-diazo-3-oxo-butanoate; With triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; In toluene; at 40 - 50 ℃; Inert atmosphere;

With methanesulfonic acid; zinc dibromide; In methanol; toluene;

ethyl acetimidate hydrochloride; 3-(S)-acetylthio-1-p-nitrobenzyloxycarbonylpyrrolidine; Further stages;

Reference yield:

(E)-(+)-(5R,6S)-3-[(1S)-1-(acetimidoylpyrrolidin-3-yl)thio]-6-[(R)-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid → (Z)-(+)-(5R,6S)-3-[(1S)-1-(acetimidoylpyrrolidin-3-yl)thio]-6-[(R)-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (87726-17-8)

Guidance literature:

With MES buffer; at 10 ℃; pH=5.0; Further Variations:; Temperatures; pH-values; Kinetics; Equilibrium constant;

DOI:10.1248/cpb.53.537

upstream raw materials:

ethyl acetimidate hydrochloride

4-nitrobenzyl 2-diazo-3-oxo-butanoate

3-(S)-acetylthio-1-p-nitrobenzyloxycarbonylpyrrolidine

Refernces

• 1、 -. "Preparation process of antibiotic drug panipenem". Paragraph 0024-0035. . Retrieved 2021/06/21.