Ceftazidime

CAS# 72558-82-8

Ceftazidime

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Chemical structure

Ceftazidime

3D structure

Chemical Properties of Ceftazidime

Cas No. 72558-82-8 SDF Download SDF
PubChem ID 5481173 Appearance Powder
Formula C22H22N6O7S2 M.Wt 546.58
Type of Compound N/A Storage Desiccate at -20°C
Synonyms GR20263
Solubility DMSO : ≥ 46 mg/mL (84.16 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
SMILES CC(C)(O/N=C(C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C([O-])=O)C[n+]3ccccc3)/c4csc(N)n4)C(O)=O
Standard InChIKey ORFOPKXBNMVMKC-DWVKKRMSSA-N
Standard InChI InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Ceftazidime Dilution Calculator

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Ceftazidime Molarity Calculator

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Preparing Stock Solutions of Ceftazidime

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8296 mL 9.1478 mL 18.2956 mL 36.5912 mL 45.739 mL
5 mM 0.3659 mL 1.8296 mL 3.6591 mL 7.3182 mL 9.1478 mL
10 mM 0.183 mL 0.9148 mL 1.8296 mL 3.6591 mL 4.5739 mL
50 mM 0.0366 mL 0.183 mL 0.3659 mL 0.7318 mL 0.9148 mL
100 mM 0.0183 mL 0.0915 mL 0.183 mL 0.3659 mL 0.4574 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Ceftazidime

Ceftazidime(GR20263) is an antibiotic useful for the treatment of a number of bacterial infections. Target: Antibacterial Ceftazidime is an antibiotic useful for the treatment of a number of bacterial infections. It is a third-generation cephalosporin. As with all antibiotics, ceftazidime is not used to treat viral infections. Cephalosporins have activity against Gram-positive and Gram-negative bacteria. The balance of activity tips toward Gram-positive organisms for earlier generations; later generations of cephalosporins have more Gram-negative coverage. Ceftazidime is one of the few in this class with activity against Pseudomonas. It is not active against Methicillin-resistant Staphylococcus aureus. From Wikipedia.

References:
[1]. http://en.wikipedia.org/wiki/Ceftazidime

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References on Ceftazidime

Molecular beta-Lactamase Characterization of Aerobic Gram-Negative Pathogens Recovered from Patients Enrolled in the Ceftazidime-Avibactam Phase 3 Trials for Complicated Intra-abdominal Infections, with Efficacies Analyzed against Susceptible and Resistant Subsets.[Pubmed:28348155]

Antimicrob Agents Chemother. 2017 May 24;61(6). pii: AAC.02447-16.

The correlation of the clinical efficacy of Ceftazidime-avibactam (plus metronidazole) with that of meropenem was evaluated in subjects infected with Gram-negative isolates having characterized beta-lactam resistance mechanisms from the complicated intra-abdominal infection (cIAI) phase 3 clinical trials. Enterobacteriaceae isolates displaying ceftriaxone and/or Ceftazidime MIC values of >/=2 mug/ml and Pseudomonas aeruginosa isolates with Ceftazidime MIC values of >/=16 mug/ml were characterized for extended-spectrum-beta-lactamase (ESBL) content. Enterobacteriaceae and P. aeruginosa isolates with imipenem and meropenem MIC values of >/=2 and >/=8 mug/ml, respectively, were tested for carbapenemase genes. The primary efficacy endpoint was clinical cure at test of cure (TOC) among the members of the microbiologically modified intention-to-treat (mMITT) population. A total of 14.5% (56/387) and 18.8% (74/394) of patients in the Ceftazidime-avibactam and meropenem arms had isolates that met the MIC screening criteria at the baseline visit, respectively. CTX-M variants alone (29.7%; 41/138) or in combination with OXA-1/30 (35.5%; 49/138), most commonly, blaCTX-M group 1 variants (79/90; 87.8%), represented the beta-lactamases most frequently observed among Enterobacteriaceae isolates. Among the patients infected with pathogens that did not meet the screening criteria, 82.2% showed clinical cure in the Ceftazidime-avibactam group versus 85.9% in the meropenem group. Among patients infected with any pathogens that met the MIC screening criteria, clinical cure rates at TOC were 87.5% and 86.5% for the Ceftazidime-avibactam and meropenem groups, respectively. Ceftazidime-avibactam had clinical cure rates of 92.5% to 90.5% among patients infected with ESBL- and/or carbapenemase-producing Enterobacteriaceae strains at the baseline visit, while meropenem showed rates of 84.9% to 85.4%. The Ceftazidime-avibactam and meropenem groups had cure rates of 75.0% and 86.7%, respectively, among patients having any pathogens producing AmpC enzymes. The efficacy of Ceftazidime-avibactam was similar to that of meropenem for treatment of cIAI caused by ESBL-producing organisms. (This study has been registered at ClinicalTrials.gov under registration no. NCT01499290 and NCT01500239.).

Ceftazidime-avibactam: novel antimicrobial combination for the treatment of complicated urinary tract infections.[Pubmed:28338347]

Future Microbiol. 2017 Jun;12:655-670.

Ceftazidime-avibactam is a combination of a third-generation cephalosporin and a novel non-beta-lactam beta-lactamase inhibitor. This combination was recently recommended for the treatment of complicated urinary tract infections, including acute pyelonephritis, in adults with limited or no alternative treatment options. The current review is aimed to determine activity, efficacy and safety of Ceftazidime-avibactam in the treatment of patients with complicated urinary tract infections.

A randomised, double-blind, phase 3 study comparing the efficacy and safety of ceftazidime/avibactam plus metronidazole versus meropenem for complicated intra-abdominal infections in hospitalised adults in Asia.[Pubmed:28363526]

Int J Antimicrob Agents. 2017 May;49(5):579-588.

Ceftazidime/avibactam comprises the broad-spectrum cephalosporin Ceftazidime and the non-beta-lactam beta-lactamase inhibitor avibactam. This phase 3, randomised, double-blind study (NCT01726023) assessed the efficacy and safety of Ceftazidime/avibactam plus metronidazole compared with meropenem in patients with complicated intra-abdominal infection (cIAI) in Asian countries. Subjects aged 18-90 years and hospitalised with cIAI requiring surgical intervention were randomised 1:1 to receive every 8 h either: Ceftazidime/avibactam (2000/500 mg, 2-h infusion) followed by metronidazole (500 mg, 60-min infusion); or meropenem (1000 mg, 30-min infusion). Non-inferiority of Ceftazidime/avibactam plus metronidazole to meropenem was concluded if the lower limit of the 95% confidence interval (CI) for the between-group difference in clinical cure rate was greater than -12.5% at the test-of-cure (TOC) visit (28-35 days after randomisation) in the clinically evaluable (CE) population. Safety was also evaluated. Of 441 subjects randomised, 432 received at least one dose of study medication (Ceftazidime/avibactam plus metronidazole, n = 215; meropenem, n = 217). In the CE population at the TOC visit, non-inferiority of Ceftazidime/avibactam plus metronidazole to meropenem was demonstrated, with clinical cure reported for 93.8% (166/177) and 94.0% (173/184) of subjects, respectively (between-group difference, -0.2, 95% CI -5.53 to 4.97). The clinical cure rate with Ceftazidime/avibactam plus metronidazole was comparable in subjects with Ceftazidime-non-susceptible and Ceftazidime-susceptible isolates (95.7% vs. 92.1%, respectively). Adverse events were similar between the study groups. Ceftazidime/avibactam plus metronidazole was non-inferior to meropenem in the treatment of cIAIs in Asian populations and was effective against Ceftazidime-non-susceptible pathogens. No new safety concerns were identified.

Antimicrobial Effects of beta-Lactams on Imipenem-Resistant Ceftazidime-Susceptible Pseudomonas aeruginosa.[Pubmed:28373200]

Antimicrob Agents Chemother. 2017 May 24;61(6). pii: AAC.00054-17.

We studied the resistance mechanism and antimicrobial effects of beta-lactams on imipenem-resistant Pseudomonas aeruginosa isolates that were susceptible to Ceftazidime as detected by time-kill curve methods. Among 215 P. aeruginosa isolates from hospitalized patients in eight hospitals in the Republic of Korea, 18 isolates (23.4% of 77 imipenem-resistant isolates) were imipenem resistant and Ceftazidime susceptible. Multilocus sequence typing revealed diverse genotypes, which indicated independent emergence. These 18 isolates were negative for carbapenemase genes. All 18 imipenem-resistant Ceftazidime-susceptible isolates showed decreased mRNA expression of oprD, and overexpression of mexB was observed in 13 isolates. In contrast, overexpression of ampC, mexD, mexF, or mexY was rarely found. Time-kill curve methods were applied to three selected imipenem-resistant Ceftazidime-susceptible isolates at a standard inoculum (5 x 10(5) CFU/ml) or at a high inoculum (5 x 10(7) CFU/ml) to evaluate the antimicrobial effects of beta-lactams. Inoculum effects were detected for all three beta-lactam antibiotics, Ceftazidime, cefepime, and piperacillin-tazobactam, against all three isolates. The antibiotics had significant killing effects in the standard inoculum, but no effects in the high inoculum were observed. Our results suggest that beta-lactam antibiotics should be used with caution in patients with imipenem-resistant Ceftazidime-susceptible P. aeruginosa infection, especially in high-inoculum infections such as endocarditis and osteomyelitis.

Description

Ceftazidime (GR20263) is a third generation cephalosporin administered intravenously or intramuscularly. Ceftazidime has a broad spectrum of in vitro activity against Gram-positive and Gram-negative aerobic bacteria. Ceftazidime is particularly active against Enterobacteriaceae (including beta-lactamase-positive strains) and is resistant to hydrolysis by most beta-lactamases.

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