Ceftazidimum

Base Information

• Chemical Name: Ceftazidimum
• CAS No.: 72558-82-8
• Molecular Formula: C₂₂H₂₂N₆O₇S₂
• Molecular Weight: 546.585
• Hs Code.: 29419000
• European Community (EC) Number: 276-715-9,616-626-8
• Wikipedia: Ceftazidime
• NCI Thesaurus Code: C66868,C90827
• RXCUI: 2191,1545984
• Mol file: 72558-82-8.mol

Synonyms:Ceftazidime;Ceftazidime Anhydrous;Ceftazidime Pentahydrate;Fortaz;Fortum;GR 20263;GR-20263;GR20263;LY 139381;LY-139381;LY139381;Pyridinium, 1-((7-(((2-amino-4-thiazolyl)((1-carboxy-1-methylethoxy)imino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-, inner salt, pentahydrate, (6R-(6alpha,7beta(Z)))-;Tazidime

Chemical Property of Ceftazidimum

Chemical Property:

• Appearance/Colour: solid
• PSA: 244.76000
• LogP: -0.38920
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: ≥21.25 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 546.09913941
• Heavy Atom Count: 37
• Complexity: 1020

Purity/Quality:

99% ^*data from raw suppliers

Ceftazidime (contains ca. 10% Na2CO3) ^*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

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Canonical SMILES: CC(C)(C(=O)O)ON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC=C4)C(=O)[O-]
• Recent ClinicalTrials: Is Cefazolin, Ceftazidime and Ciprofloxacin Dosing Optimal in Hemodialysis Patients?
• Recent EU Clinical Trials: Intrapulmonary penetration of ceftolozane / tazobactam and ceftazidime / avibactam administered in continuous infusion in critically ill patients with nosocomial pneumonia
• Recent NIPH Clinical Trials: None
• Description: In ceftazidime the oxime moiety is more complex, containing two methyl groups and a carboxylic acid. This assemblage conveys even more pronounced β-lactamase stability, greater anti–Pseudomonas aerugi nosa, and increased activity against Gram-positive organisms. The C-3 side chain has been replaced by a charged pyridinium moiety. The latter considerably enhances water solubility and also highly activates the β-lactam bond toward cleavage. The drug must be protected against heat and light and may darken without significant loss of potency. It is not stable under some conditions. such as the presence of aminoglycosides and vancomycin. It also is attacked readily in sodium bicarbonate solutions. Resistance is mediated by chromosomally mediated β-lactamases and by lack of penetration into target bacteria. Otherwise, it has a very broad antibacterial spectrum.
• Uses: 5-HT agonist, anti-migrane pyrimidine synthesis inhibitor disease-modifying antirheumatic drug Like most of the third-generation cephalosporin antibiotics described above, ceftazidime has a broad spectrum of antimicrobial action, including the most clinically important microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is resistant to most beta-lactamases of Gram-positive and Gram-negative bacteria. It is used for treating most serious bacterial infections. Synonyms of this drug are fortum, ceftim, stacef, and tazicef. Third generation cephalosporin antibiotic. Antibacterial
• Therapeutic Function: Antibiotic
• Clinical Use: Antibacterial agent
• Drug interactions: Potentially hazardous interactions with other drugsAnticoagulants: effects of coumarins may be enhanced.Ciclosporin: may cause increased ciclosporin levels.

Technology Process of Ceftazidimum

There total 12 articles about Ceftazidimum 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: 98.9%

pyridine (110-86-1) + (Z)-(2-carboxyprop-2-oxyimino)-2-(2-aminothiazole-4-yl)-acetylchloride monohydrochloride (354808-44-9) + 7-Aminocephalosporanic acid (957-68-6) → ceftazidime (72558-82-8,97148-38-4,238093-13-5)

Guidance literature:

at -16 ℃; for 2h; Concentration; Temperature; Sonication; Industrial scale;

Reference yield: 64.0%

ceftazidime HI salt (139975-09-0) → ceftazidime (72558-82-8,97148-38-4,238093-13-5)

Guidance literature:

With Amberlite LA-1; 4-methyl-2-pentanone; In water; for 0.333333h;

DOI:10.1021/jo00011a034

Reference yield:

(Z)-7-(2-(2-aminothiazol-4-yl)-2-(((1-(tertbutoxy)-2-methyl-1-oxopropan-2-yl)oxy)amino)acetamido)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylate (102772-66-7) → ceftazidime (72558-82-8,97148-38-4,238093-13-5)

Guidance literature:

(Z)-7-(2-(2-aminothiazol-4-yl)-2-(((1-(tertbutoxy)-2-methyl-1-oxopropan-2-yl)oxy)amino)acetamido)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylate; With hydrogenchloride; formic acid; In water; at 25 ℃; for 2h;

With Amberlite resin; In water; pH=4.0;

upstream raw materials:

ceftazidime HI salt

1-[(6R,7R)-7-{2-[(Z)-1-tert-Butoxycarbonyl-1-methyl-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-2-(4-methoxy-benzyloxycarbonyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-pyridinium; iodide

diethyl ether

glyoxylic acid aldoxime

Downstream raw materials:

(6R,7R)-7-[2-(2-amino-4-thiazolyl)-2-(Z)-(2,2-dimethylacetoxyimino)acetamido]-3-[(pyridinium)methyl]-2-cephem-4-carboxylate

pyridine

C₂₂H₂₂N₆O₇S₂

Refernces

• 1、 -. "One-pot method of preparing Ceftazidime". . . Retrieved 2017/09/01.
• 2、 -. "IMPROVED PROCESS FOR THE PREPARATION OF CEPHALOSPORIN ANTIBIOTICS". Page/Page column 12-13. . Retrieved 2008/06/13.