Identification

Name
Ceftizoxime
Accession Number
DB01332
Description

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Approved, Withdrawn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
Thumb
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.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1B
inhibitor
Escherichia coli (strain K12)
UPeptidoglycan transpeptidase
binder
UD-alanyl-D-alanine carboxypeptidase DacC
binder
Escherichia 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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Toxicity
Not Available
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.
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.
DrugInteraction
AbacavirCeftizoxime may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Ceftizoxime.
AcarboseCeftizoxime may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacCeftizoxime may decrease the excretion rate of Aceclofenac which could result in a higher serum level.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Ceftizoxime is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Ceftizoxime is combined with Acenocoumarol.
AcetaminophenCeftizoxime may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideThe excretion of Ceftizoxime can be decreased when combined with Acetazolamide.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Ceftizoxime.
AclidiniumCeftizoxime may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ceftizoxime sodium26337D5X8868401-82-1ADLFUPFRVXCDMO-LIGXYSTNSA-M
International/Other Brands
Epocelin (Choseido Pharmaceutical)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CefizoxSolution2 g/50mLIntravenousAstellas Pharma Inc2006-01-04Not applicableUS flag
CefizoxPowder, for solution2 gIntramuscular; IntravenousGlaxosmithkline Inc1988-12-312005-10-19Canada flag
CefizoxInjection, powder, lyophilized, for solution1 g/1Intramuscular; IntravenousFujisawa Healthcare, Inc.2007-08-04Not applicableUS flag
CefizoxInjection, powder, lyophilized, for solution1 g/1IntravenousFujisawa Healthcare, Inc.2006-06-08Not applicableUS flag
CefizoxInjection, powder, lyophilized, for solution500 mg/1Intramuscular; IntravenousFujisawa Healthcare, Inc.2007-08-04Not applicableUS flag
CefizoxSolution1 g/50mLIntravenousAstellas Pharma Inc2006-01-04Not applicableUS flag
CefizoxPowder, for solution1 gIntramuscular; IntravenousGlaxosmithkline Inc1988-12-312005-10-19Canada flag
CefizoxInjection, powder, lyophilized, for solution2 g/1Intramuscular; IntravenousFujisawa Healthcare, Inc.2007-08-04Not applicableUS flag
CefizoxInjection, powder, lyophilized, for solution2 g/1IntravenousFujisawa Healthcare, Inc.2006-06-08Not applicableUS flag
CefizoxInjection, powder, lyophilized, for solution2 g/1Intramuscular; IntravenousFujisawa Healthcare, Inc.2007-08-04Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
J01DD07 — Ceftizoxime
Drug Categories
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)

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][[email protected]]12SCC=C(N1C(=O)[[email protected]]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
  1. 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. [PubMed:3888599]
Human Metabolome Database
HMDB0015427
KEGG Compound
C06890
PubChem Compound
6533629
PubChem Substance
46505647
ChemSpider
5018818
BindingDB
237182
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedPreventionCaesarean1
0Unknown StatusTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Baxter International Inc.
  • GlaxoSmithKline Inc.
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous2 g/1
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous500 mg/1
Injection, powder, lyophilized, for solutionIntravenous1 g/1
Injection, powder, lyophilized, for solutionIntravenous2 g/1
Powder, for solutionIntramuscular; Intravenous1 g
Powder, for solutionIntramuscular; Intravenous2 g
SolutionIntravenous1 g/50mL
SolutionIntravenous2 g/50mL
Injection, solutionIntramuscular1 g
Injection, solutionIntramuscular; Intravenous1 g
Injection, solution1 g
Injection, solution500 mg
Injection, solutionIntramuscular500 mg
InjectionIntramuscular; Intravenous500 mg
Injection, solutionIntramuscular1000 mg
Injection, powder, for solution
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA1321580No1993-08-242010-08-24Canada flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)277Takaya, T., Masugi, T., Takasugi, H. and Kochi, H.;U.S. Patent 4,166,115; assigned to Fuji- sawa Pharmaceutical & ., Ltd.
Predicted Properties
PropertyValueSource
Water Solubility0.229 mg/mLALOGPS
logP0.4ALOGPS
logP-0.85ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area147.21 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.9 m3·mol-1ChemAxon
Polarizability35.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7379
Blood Brain Barrier-0.9823
Caco-2 permeable-0.7273
P-glycoprotein substrateSubstrate0.5819
P-glycoprotein inhibitor INon-inhibitor0.9194
P-glycoprotein inhibitor IINon-inhibitor0.8007
Renal organic cation transporterNon-inhibitor0.8794
CYP450 2C9 substrateNon-substrate0.804
CYP450 2D6 substrateNon-substrate0.8281
CYP450 3A4 substrateNon-substrate0.5393
CYP450 1A2 substrateNon-inhibitor0.749
CYP450 2C9 inhibitorNon-inhibitor0.8202
CYP450 2D6 inhibitorNon-inhibitor0.9005
CYP450 2C19 inhibitorNon-inhibitor0.7881
CYP450 3A4 inhibitorNon-inhibitor0.7951
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9449
Ames testNon AMES toxic0.7835
CarcinogenicityNon-carcinogens0.8563
BiodegradationNot ready biodegradable0.9906
Rat acute toxicity1.8332 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9903
hERG inhibition (predictor II)Non-inhibitor0.918
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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
  1. 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. [PubMed:7018389]
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
  1. 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. [PubMed:7018389]
3. Peptidoglycan transpeptidase
Kind
Group
Organism
Not Available
Pharmacological action
Unknown
Actions
Binder
The enzyme peptidoglycan transpeptidase, which catalyzes cell wall cross-linking of bacteria.
References
  1. 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. [PubMed:3888599]
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
  1. 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. [PubMed:3888599]

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
  1. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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. [PubMed:19953504]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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. [PubMed:19953504]

Drug created on June 30, 2007 12:05 / Updated on June 12, 2020 11:41

Ddi 3