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Ceftazidim

Biotum

HCID 73415817
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
72558-82-8
Standard-SMILES
CC(C)(O/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[n+]3ccccc3)CS[C@H]12)c1csc(N)n1)C(=O)[O-].[H+]
InChIKey
ORFOPKXBNMVMKC-DWVKKRMSSA-N
Summenformel
C22H22N6O7S2
Durchschnittliche Molmasse
546,6 g/mol
Monoisotopische Masse
546,09913941

Überblick

Bacteria possess a cell wall comprising a glycopeptide polymer commonly known as peptidoglycan, which is synthesized and remodelled through the action of a family of enzymes known as "penicillin-binding proteins" (PBPs). β-lactam antibiotics, including cephalosporins, are PBP inhibitors that, through inhibition of essential PBPs, result in impaired cell wall homeostasis, loss of cell integrity, and ultimately bacterial cell death. Ceftazidime is a third-generation cephalosporin with broad-spectrum antibacterial activity, including against some treatment-resistant bacteria such as Pseudomonas aeruginosa. Ceftazidime was approved by the FDA on July 19, 1985, and is currently available either alone or in combination with the non-β-lactam β-lactamase inhibitor [avibactam] to treat a variety of bacterial infections.

Namen und Bezeichner

Bevorzugter Name
Biotum
IUPAC
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxylatopropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydron
Lokaler Name
Ceftazidim
Englischer Name
CeftazidiMe
Summenformel
C22H22N6O7S2
Molmasse
546.57

Namen und Synonyme

ModacinbiotumTizimeZidimUNII-DZR1ENT301EINECS 276-715-9SN 401NSC 759260BRN 4344904Pyridinium, 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)-, hydroxide, inner salt, (6R-(6-alpha,7-beta-(Z)))-hyCeftazidiMe with SodiuM Carbonate
Weitere Namen anzeigen
CEFTAZIDINECEFTAZIDIME HYDRATEcazTazidimeFortazCeptazCeftazidime CRSpyridinium,1-((7-(((2-amino-4-thiazolyl)((1-carboxy-1-methylethoxy)imino)acety

Datenbank-Bezeichner

CAS
72558-82-8、78439-06-2

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
248 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
12
Frei drehbare Bindungen
7
Schwere Atome
37
Formalladung
0
Komplexität
1.020

Experimentelle und physikochemische Eigenschaften

LogP-1.60
Solubility5.73e-03 g/L
Melting Point103-113
Physical DescriptionSolid

Physikochemische Eigenschaften

storage temp.
2 · under inert gas (nitrogen or Argon) at 2–8 °C
Löslichkeit
21.25 mg/mL · ≥21.25 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O
Aggregatzustand
powder to crystal
Farbe
White to Orange to Green
Merck
14 · 14,1946
Stabilität
Stable, but keep refrigerated. Incompatible with strong oxidizing agents, nitric acid, permanganates, peroxides.
InChIKey
ORFOPKXBNMVMKC-VNOLCAKANA-N
SMILES
C(C1=C(CS[C@]2([H])[C@H](NC(=O)/C(/C3N=C(N)SC=3)=N\OC(C)(C)C(=O)O)C(=O)N12)C[N+]1=CC=CC=C1)(=O)[O-] |&1:5,7,r|

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheitsdaten

hs_code
29419000
RTECS-Nr.
UU2225000
risk_code
20/21/22-36/37/38
hazard_code
Xn
safety_code
26-36

Chemie und Industrie

Pharmakologische Informationen

Protein BindingCeftazidime plasma protein binding ranges from 5-22.8% (typically less than 10%) and is independent of concentration. Ceftazidime has been shown to bind human serum albumin.
Pharmacodynamics · 1 Eintrag

Ceftazidime is a semisynthetic, broad-spectrum, third-generation cephalosporin antibiotic that is bactericidal through inhibition of enzymes responsible for cell-wall synthesis, primarily penicillin-binding protein 3 (PBP3). Among cephalosporins, ceftazidime is notable for its resistance to numerous β-lactamases and its broad spectrum of activity against Gram-negative bacteria, including _Pseudomonas aeruginosa_. However, it is less active than first- and second-generation cephalosporins against _Staphylococcus aureus_ and other Gram-positive bacteria and also has low activity against anaerobes. Ceftazidime has confirmed activity against clinically relevant Gram-negative bacteria including _Citrobacter_ spp., _Enterobacter_ spp., _Klebsiella_ spp., _Proteus_ spp., _Serratia spp., _Escherichia coli_, _Haemophilus influenzae_, _Neisseria meningitidis_, _Pseudomonas aeruginosa_, and some Gram-positive bacteria including _Staphylococcus_ spp. and _Streptococcus_ spp. There are also _in vitro_ data for ceftazidime efficacy against a wide variety of other bacteria, such as _Acinetobacter baumannii_ and _Neisseria gonorrhoeae_, but no clear clinical studies to support the use of ceftazidime for infections caused by these bacteria. Although β-lactam antibiotics like ceftazidime are generally well tolerated, there remains a risk of serious acute hypersensitivity reactions, which is higher in patients with a known allergy to ceftazidime or any other β-lactam antibiotic. As with all antibiotics, ceftazidime may result in the overgrowth of non-susceptible organisms and potentially serious effects including _Clostridium difficile_-associated diarrhea (CDAD); CDAD should be considered in patients who develop diarrhea and, in confirmed cases, supportive care initiated immediately. Ceftazidime is primarily renally excreted such that high and prolonged serum concentrations can occur in patients with renal insufficiency, leading to seizures, nonconvulsive status epilepticus (NCSE), encephalopathy, coma, asterixis, neuromuscular excitability, and myoclonia. Treatment may lead to the development or induction of resistance with a risk of treatment failure. Periodic susceptibility testing should be considered, and monotherapy failure may necessitate the addition of another antibiotic such as an aminoglycoside. Cephalosporin use may decrease prothrombin activity, which may be improved by exogenous vitamin K. Inadvertent intra-arterial administration of ceftazidime may result in distal necrosis.

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PubChem CID
73415817
Mechanism of Action · 1 Eintrag

The bacterial cell wall, which is located at the periphery of Gram-positive bacteria and within the periplasm of Gram-negative bacteria, comprises a glycopeptide polymer synthesized through cross-linking of glycans to peptide stems on alternating saccharides, which is known commonly as peptidoglycan. Cell wall formation, recycling, and remodelling require numerous enzymes, including a family of enzymes with similar active site character despite distinct and sometimes overlapping roles as carboxypeptidases, endopeptidases, transpeptidases, and transglycosylases, known as "penicillin-binding proteins" (PBPs). The number of PBPs differs between bacteria, in which some are considered essential and others redundant. In general, inhibition of one or more essential PBPs results in impaired cell wall homeostasis, loss of cell integrity, and is ultimately bactericidal. Ceftazidime is a semisynthetic third-generation cephalosporin with broad activity against numerous Gram-negative and some Gram-positive bacteria. Like other β-lactam antibiotics, ceftazidime exhibits its bactericidal effect primarily through direct inhibition of specific PBPs in susceptible bacteria. _In vitro_ experiments in Gram-negative bacteria such as _Escherichia coli_, _Pseudomonas aeruginosa_, _Acinetobacter baumannii_, and _Klebsiella pneumoniae_ suggest that ceftazidime primarily binds to PBP3, with weaker binding to PBP1a/1b and PBP2 as well; although binding to other PBPs, such as PBP4, is detectable, the concentrations required are much greater than those achieved clinically. Similarly, ceftazidime showed binding to _Staphylococcus aureus_ PBP 1, 2, and 3 with a much lower affinity for PBP4. Recent data for _Mycobacterium abcessus_ suggest that ceftazidime can inhibit PonA1, PonA2, and PbpA at intermediate concentrations.

Biological Half-Life · 1 Eintrag

Ceftazidime has an elimination half-life of 1.5-2.8 hours in healthy subjects. As ceftazidime is primarily renally excreted, its half-life is significantly prolonged in patients with renal impairment. In patients with creatinine clearance < 12 mL/min, the half-life is prolonged to between 14 and 30 hours.

Metabolism/MetabolitesCeftazidime is not appreciably metabolized.
Absorption, Distribution and Excretion · 4 Einträge

Ceftazidime administered intravenously in healthy males produced mean Cmax values of between 42 and 170 μg/mL for doses between 500 mg and 2 g, and are reached immediately following the end of the infusion period. The Cmax for 1 g of ceftazidime administered intramuscularly is attained approximately one hour following injection and is between 37 and 43 mg/L. Following intramuscular administration of 500 mg and 1 g of ceftazidime, the serum concentration remained above 4 μg/mL for six and eight hours, respectively. Ceftazidime Cmax and AUC show linear proportionality to the dose over the therapeutic range. In individuals with normal renal function, ceftazidime given intravenously every eight hours for 10 days as either 1 or 2 g doses showed no accumulation.

Approximately 80% to 90% of an intramuscular or intravenous dose of ceftazidime is excreted unchanged by the kidneys over a 24-hour period. When administered intravenously, 50% of the dose appears in the urine within two hours, with another 32% of the dose appearing by eight hours post-administration.

Ceftazidime has a volume of distribution of 15-20 L.

The mean renal clearance of ceftazidime in healthy subjects ranges from 72 to 141 mL/min while the calculated plasma clearance is approximately 115 mL/min.

Cellular LocationsCytoplasm
Anwendungen · 2 Einträge

BeschreibungIn 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.

VerwendenLike 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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Formic acid1-HydroxybenzotriazolN,N-DimethylformamidNatriumchloridAnisolTrifluoressigsäurecolumn-layer chromatographic silica gelTriphenylstibinTert-butyl esterDiisopropyletherDicyclohexylcarbodiimidPyridinα,α-Dimethoxytoluol

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Ergänzende Hinweise

DefinitionChEBI: A cephalosporin bearing pyridinium-1-ylmethyl and {[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.