Ceftizoxime
Ceftizoxime
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Ceftizoxime

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Catalog Number PR68401810
CAS 68401-81-0
Structure
Description Ceftizoxime is a parenteral third-generation cephalosporin, bearing a 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino group at the 7beta-position. It has a role as an antibacterial drug. It is a conjugate acid of a ceftizoxime(1-).
Synonyms Ceftizoxima; Ceftizoximum; Cefizox
IUPAC Name (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Weight 383.4
Molecular Formula C13H13N5O5S2
InChI NNULBSISHYWZJU-LLKWHZGFSA-N
InChI Key InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
Drug Categories Amides; Anti-Bacterial Agents; Anti-Infective Agents; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; beta-Lactams; Cephalosporins; Heterocyclic Compounds, Fused-Ring; Lactams; Nephrotoxic agents; OAT1/SLC22A6 inhibitors; OAT1/SLC22A6 Substrates; OAT3/SLC22A8 Inhibitors; OAT3/SLC22A8 Substrates; Sulfur Compounds; Thiazines; Third-Generation Cephalosporins
Drug Interactions Abacavir-Ceftizoxime may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab-The therapeutic efficacy of Abciximab can be decreased when used in combination with Ceftizoxime.
Acamprosate-The excretion of Acamprosate can be decreased when combined with Ceftizoxime.
Aceclofenac-The risk or severity of nephrotoxicity can be increased when Ceftizoxime is combined with Aceclofenac.
Acemetacin-The risk or severity of nephrotoxicity can be increased when Ceftizoxime is combined with Acemetacin.
Isomeric SMILES CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)O
Type Small Molecule
Pharmacology

Indications

Ceftizoxime was traditionally prescribed for managing infections caused by bacteria that are susceptible to its effects. This indicates that it was effective against specific bacterial strains, providing a targeted approach to treating such infections.

Pharmacodynamics

Ceftizoxime demonstrates significant resistance to a wide array of beta-lactamases, making it potent against a diverse range of both aerobic and anaerobic bacteria, including gram-positive and gram-negative organisms. This resistance enhances its efficacy in treating infections and contributes to its safety profile, which is favorable for elderly patients and those with hematologic disorders.

Metabolism

Ceftizoxime remains unchanged in the body and is primarily excreted by the kidneys over a 24-hour period. This lack of metabolic transformation highlights its direct elimination pathway, which is an important consideration for dosing and efficacy.

Mechanism of Action

Ceftizoxime is an aminothiazolyl cephalosporin known for its broad-spectrum efficacy against numerous gram-negative pathogens commonly associated with nosocomial infections. It exhibits remarkable stability against beta-lactamase enzymes and demonstrates substantial in vitro activity against organisms such as Haemophilus influenzae, Neisseria gonorrhoeae, and Klebsiella pneumoniae. As a beta-lactam antibiotic, ceftizoxime exerts its action by binding to specific penicillin-binding proteins (PBPs) within the bacterial cell wall. This interaction halts the third and final phase of cell wall synthesis, leading to cell lysis, which is facilitated by the autolytic enzymes within the bacterial cell. There is also a potential role of ceftizoxime in disrupting an autolysin inhibitor, further promoting bacterial cell wall degradation.

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