Identification
- Summary
Ceftizoxime is a third-generation cephalosporin antibiotic used in the treatment of various bacterial infections, including lower respiratory tract infection, urinary tract infection, and gonorrhea.
- Brand Names
- Cefizox
- Generic Name
- Ceftizoxime
- DrugBank Accession Number
- DB01332
- Background
A semisynthetic cephalosporin antibiotic which can be administered intravenously or by suppository. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. It has few side effects and is reported to be safe and effective in aged patients and in patients with hematologic disorders.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Ceftizoxime (DB01332)
- Weight
- Average: 383.403
Monoisotopic: 383.035809931 - Chemical Formula
- C13H13N5O5S2
- Synonyms
- 7-[2-(2-Amino-thiazol-4-yl)-2-methoxyimino-acetylamino]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Ceftizoxima
- Ceftizoxime
- Ceftizoximum
- syn-7-(2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylic acid
- External IDs
- FK 749
- FR 13749
Pharmacology
- Indication
Cetizoxime was previously indicated for the treatment of infections due to susceptible strains of bacteria.
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- Contraindications & Blackbox Warnings
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Ceftizoxime is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. It has few side effects and is reported to be safe and effective in aged patients and in patients with hematologic disorders.
- Mechanism of action
Ceftizoxime is an aminothiazolyl cephalosporin with an extended spectrum of activity against many gram-negative, nosocomially acquired pathogens. It has excellent beta-lactamase stability, with good in vitro activity against Haemophilus influenzae, Neisseria gonorrhoeae and Klebsiella pneumoniae. Ceftizoxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that ceftizoxime interferes with an autolysin inhibitor.
Target Actions Organism APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) UPeptidoglycan transpeptidase binderUD-alanyl-D-alanine carboxypeptidase DacC binderEscherichia coli (strain K12) - Absorption
Not Available
- Volume of distribution
The mean apparent volume of distribution ranges between 15 - 28L.1
- Protein binding
30% protein-bound across the standard concentration range.1
- Metabolism
Ceftizoxime is not metabolized and is excreted virtually unchanged by the kidneys in 24 hours.
- Route of elimination
Excreted virtually unchanged by the kidneys in 24 hours.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir 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. Acenocoumarol The risk or severity of bleeding can be increased when Ceftizoxime is combined with Acenocoumarol. Acetaminophen Ceftizoxime may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide The excretion of Ceftizoxime can be decreased when combined with Acetazolamide. Acetylsalicylic acid The excretion of Ceftizoxime can be decreased when combined with Acetylsalicylic acid. Aclidinium Ceftizoxime may decrease the excretion rate of Aclidinium which could result in a higher serum level. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Ceftizoxime sodium 26337D5X88 68401-82-1 ADLFUPFRVXCDMO-LIGXYSTNSA-M - International/Other Brands
- Epocelin (Choseido Pharmaceutical)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefizox Solution 1 g/50mL Intravenous Astellas Pharma Inc 2006-01-04 Not applicable US 
Cefizox Powder, for solution 1 g / vial Intramuscular; Intravenous Glaxosmithkline Inc 1988-12-31 2005-10-19 Canada 
Cefizox Injection, powder, lyophilized, for solution 2 g/1 Intramuscular; Intravenous Fujisawa Healthcare, Inc. 2007-08-04 Not applicable US Cefizox Injection, powder, lyophilized, for solution 2 g/1 Intramuscular; Intravenous Fujisawa Healthcare, Inc. 2007-08-04 Not applicable US Cefizox Injection, powder, lyophilized, for solution 2 g/1 Intravenous Fujisawa Healthcare, Inc. 2006-06-08 Not applicable US Cefizox Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous Fujisawa Healthcare, Inc. 2007-08-04 Not applicable US Cefizox Powder, for solution 2 g Intramuscular; Intravenous Glaxosmithkline Inc 1988-12-31 2005-10-19 Canada Cefizox Solution 2 g/50mL Intravenous Astellas Pharma Inc 2006-01-04 Not applicable US Cefizox Injection, powder, lyophilized, for solution 1 g/1 Intramuscular; Intravenous Fujisawa Healthcare, Inc. 2007-08-04 Not applicable US Cefizox Injection, powder, lyophilized, for solution 1 g/1 Intravenous Fujisawa Healthcare, Inc. 2006-06-08 Not applicable US
Categories
- ATC Codes
- J01DD07 — Ceftizoxime
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephacetrile
- 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives show 9 more
- Substituents
- 1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Azole show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:553473)
- Affected organisms
- Pseudomonas aeruginosa
- Streptococcus pyogenes
- Streptococcus pneumoniae
- Streptococcus agalactiae
- Neisseria meningitidis
- Haemophilus influenzae
- Neisseria gonorrhoeae
- Escherichia coli
- Staphylococcus aureus
- Moraxella catarrhalis
- Staphylococcus epidermidis
- Serratia marcescens
- Proteus vulgaris
- Enterobacter
- Proteus mirabilis
- Providencia stuartii
- Providencia rettgeri
- Morganella morganii
- Bacteroides
- Peptostreptococcus
- Klebsiella pneumoniae
- Aeromonas hydrophila
- Citrobacter spp.
- Peptococcus spp.
Chemical Identifiers
- UNII
- C43C467DPE
- CAS number
- 68401-81-0
- InChI Key
- NNULBSISHYWZJU-LLKWHZGFSA-N
- InChI
- 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
- IUPAC Name
- (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
References
- Synthesis Reference
Norio Ohnishi, Rinta Ibuki, "Method for preparing stable crystals of salt of Ceftizoxime." U.S. Patent US4390694, issued October, 1981.
US4390694- General References
- Richards DM, Heel RC: Ceftizoxime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1985 Apr;29(4):281-329. doi: 10.2165/00003495-198529040-00001. [Article]
- External Links
- Human Metabolome Database
- HMDB0015427
- KEGG Compound
- C06890
- PubChem Compound
- 6533629
- PubChem Substance
- 46505647
- ChemSpider
- 5018818
- BindingDB
- 237182
- 2192
- ChEBI
- 553473
- ChEMBL
- CHEMBL528
- ZINC
- ZINC000003830477
- Therapeutic Targets Database
- DAP000453
- PharmGKB
- PA164748758
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ceftizoxime
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Caesarean 1 0 Terminated Treatment Osteomyelitis 1 Not Available Recruiting Not Available Augmented Renal Clearance (ARC) / Meningitis, Bacterial 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Baxter International Inc.
- GlaxoSmithKline Inc.
- Dosage Forms
Form Route Strength Injection, powder, lyophilized, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous 2 g/1 Injection, powder, lyophilized, for solution Intramuscular; Intravenous 500 mg/1 Injection, powder, lyophilized, for solution Intravenous 1 g/1 Injection, powder, lyophilized, for solution Intravenous 2 g/1 Powder, for solution Intramuscular; Intravenous 1 g / vial Powder, for solution Intramuscular; Intravenous 2 g Solution Intravenous 1 g/50mL Solution Intravenous 2 g/50mL Injection, solution Intramuscular 1 g Injection, solution Intramuscular; Intravenous 1 g Injection, solution 1 g Injection, solution 500 mg Injection, solution Intramuscular 500 mg Injection Intramuscular; Intravenous 500 mg Injection, solution Intramuscular 1000 mg Injection, powder, for solution Injection, powder, for solution Intramuscular Injection, powder, for solution Intravenous - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA1321580 No 1993-08-24 2010-08-24 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 277 Takaya, T., Masugi, T., Takasugi, H. and Kochi, H.;U.S. Patent 4,166,115; assigned to Fuji- sawa Pharmaceutical & ., Ltd. - Predicted Properties
Property Value Source Water Solubility 0.229 mg/mL ALOGPS logP 0.4 ALOGPS logP -0.94 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 2.66 Chemaxon pKa (Strongest Basic) 3.6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 147.21 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 89.9 m3·mol-1 Chemaxon Polarizability 35.38 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7379 Blood Brain Barrier - 0.9823 Caco-2 permeable - 0.7273 P-glycoprotein substrate Substrate 0.5819 P-glycoprotein inhibitor I Non-inhibitor 0.9194 P-glycoprotein inhibitor II Non-inhibitor 0.8007 Renal organic cation transporter Non-inhibitor 0.8794 CYP450 2C9 substrate Non-substrate 0.804 CYP450 2D6 substrate Non-substrate 0.8281 CYP450 3A4 substrate Non-substrate 0.5393 CYP450 1A2 substrate Non-inhibitor 0.749 CYP450 2C9 inhibitor Non-inhibitor 0.8202 CYP450 2D6 inhibitor Non-inhibitor 0.9005 CYP450 2C19 inhibitor Non-inhibitor 0.7881 CYP450 3A4 inhibitor Non-inhibitor 0.7951 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9449 Ames test Non AMES toxic 0.7835 Carcinogenicity Non-carcinogens 0.8563 Biodegradation Not ready biodegradable 0.9906 Rat acute toxicity 1.8332 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9903 hERG inhibition (predictor II) Non-inhibitor 0.918
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- mrcA
- Uniprot ID
- P02918
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 93635.545 Da
References
- Shigi Y, Kojo H, Wakasugi M, Nishida M: Differences between ceftizoxime and its stereoisomer in antibacterial activity and affinity for penicillin-binding proteins. Antimicrob Agents Chemother. 1981 Mar;19(3):393-6. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- mrcB
- Uniprot ID
- P02919
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 94291.875 Da
References
- Shigi Y, Kojo H, Wakasugi M, Nishida M: Differences between ceftizoxime and its stereoisomer in antibacterial activity and affinity for penicillin-binding proteins. Antimicrob Agents Chemother. 1981 Mar;19(3):393-6. [Article]
3. Peptidoglycan transpeptidase
Unknown
Binder
References
- Richards DM, Heel RC: Ceftizoxime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1985 Apr;29(4):281-329. doi: 10.2165/00003495-198529040-00001. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Gene Name
- dacC
- Uniprot ID
- P08506
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacC
- Molecular Weight
- 43608.595 Da
References
- Richards DM, Heel RC: Ceftizoxime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1985 Apr;29(4):281-329. doi: 10.2165/00003495-198529040-00001. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Substrate and inhibitor profile were studied in vitro using human OAT1 expressed on HEK293 cells.
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Substrate and inhibitor profile were studied in vitro using human OAT3 expressed on HEK293 cells.
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
Drug created at June 30, 2007 18:05 / Updated at March 03, 2023 17:50