Cefoperazone

Base Information

• Chemical Name: Cefoperazone
• CAS No.: 62893-19-0
• Deprecated CAS: 72448-63-6
• Molecular Formula: C₂₅H₂₇N₉O₈S₂
• Molecular Weight: 645.677
• Hs Code.: 29419000
• European Community (EC) Number: 263-749-4,263-751-5,663-513-4
• UNII: 7U75I1278D
• DSSTox Substance ID: DTXSID2022759
• Nikkaji Number: J19.295C
• Wikipedia: Cefoperazone
• Wikidata: Q2325775
• NCI Thesaurus Code: C61663
• Pharos Ligand ID: 97K8CKBA4QBX
• Metabolomics Workbench ID: 144825
• ChEMBL ID: CHEMBL507674
• Mol file: 62893-19-0.mol

Synonyms:Céfobis;Cefobid;Cefoperazon;Cefoperazone;Cefoperazone Sodium;Cefoperazone Sodium Salt;Salt, Cefoperazone Sodium;Sodium Salt, Cefoperazone;Sodium, Cefoperazone;T 1551;T-1551;T1551

Chemical Property of Cefoperazone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 169-171oC
• Refractive Index: 1.819
• PKA: pKa 2.6 (Uncertain)
• PSA: 270.86000
• Density: 1.77 g/cm³
• LogP: -0.51650
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 9
• Exact Mass: 645.14240120
• Heavy Atom Count: 44
• Complexity: 1250

Purity/Quality:

99% ^*data from raw suppliers

CefoperazoneAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=C(C=C2)O)C(=O)NC3C4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
• Isomeric SMILES: CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@H]3[C@@H]4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
• Recent ClinicalTrials: Multi-center Clinical Study of Early Antibios of Severe Acute Pancreatitis
• Description: Cefoperazone has a C-7 side chain reminiscent of piperacillin's and also possesses the C-3 side chain (MTT ) that often is associated with the bleeding and alcohol intolerance problems among patients taking cephalosporins. Its useful activity against pseudomonads partly compensates for this, although it is not potent enough to be used as a single agent against this difficult pathogen. The C-7 side chain does not convey sufficient resistance to many β-lactamases, although the addition of clavulanic acid or sulbactam would presumably help.
• Uses: Antibacterial. Cefoperazone also has a broad spectrum of antimicrobial action, including most clinically significant microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is stable with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria. Cefoperazone is used for bacterial infections of the lower respiratory tract, urinary and sexual tracts, bones, joints, skin, soft tissues, abdominal, and gynecological infections. Synonyms of this drug are cefazon, cefobid, cefobis, and many others. Cefoperazone acid is an antimicrobial β-lactamase inhibitor.
• Therapeutic Function: Antibiotic

Technology Process of Cefoperazone

There total 9 articles about Cefoperazone 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: 76.2%

C13H20N6O3S2Si*ClH + (R)-<<(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl>amino>(4-hydroxyphenyl)acetic acid (62893-24-7,79868-75-0) → cefoperazone (62893-19-0,68779-10-2)

Guidance literature:

With benzotriazol-1-yl diethyl phosphate; triethylamine; In N,N-dimethyl-formamide; at 28 ℃; for 2h;

Reference yield: 42.0%

C18H19N7O5S2 + 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride (59703-00-3) → cefoperazone (62893-19-0,68779-10-2)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; at 20 ℃;

Reference yield:

D-(-)-2-[(4-ethyl-2,3-dioxo-1-piperazinyl)amido]- 2-(4-hydroxyphenyl)acetic acid chloride (74769-12-3) + C10H14N6O3S2 → cefoperazone (62893-19-0,68779-10-2)

Guidance literature:

D-(-)-2-[(4-ethyl-2,3-dioxo-1-piperazinyl)amido]- 2-(4-hydroxyphenyl)acetic acid chloride; C₁₀H₁₄N₆O₃S₂; at -30 ℃; for 2h;

With sodium hydrogencarbonate; In water; for 0.166667h;

upstream raw materials:

4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride

D-(-)-2-[(4-ethyl-2,3-dioxo-1-piperazinyl)amido]- 2-(4-hydroxyphenyl)acetic acid chloride

7-Aminocephalosporanic acid

(R)-<<(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl>amino>(4-hydroxyphenyl)acetic acid

Downstream raw materials:

2-methylthiazol-4-carbonitrile

pyrrolidine-3-carboxylic acid

2,3-dimethylpentan-2-ol

1-Methoxy-2-methylpropan-2-ol

Refernces

• 1、 -. "Preparation method of cefoperazone acid". Paragraph 0029; 0030; 0031; 0032; 0033. . Retrieved 2019/01/06.
• 2、 -. "Process for the preparation of keto acid [...]". . . Retrieved 2017/03/14.