This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Ceftiofur
DrugBank Accession Number
DB11485
Background

Ceftiofur is a third generation cephalosporin antibiotic, first described in 1987, and now used in veterinary medicine. It is marketed by pharmaceutical company Zoetis as Excenel, and is the active ingredient in that company's Specramast LC (lactating cow formula) product. It is resistant to hydrolysis by beta-lactamase, and has activity against both Gram-positive and Gram-negative bacteria. E. coli strains resistant to ceftiofur have been reported. The metabolite desfurolyceftiofur also has antibiotic activity, consequently the two compounds are measured together to monitor for antibiotic activity in the milk.

Type
Small Molecule
Groups
Vet approved
Structure
Thumb
Weight
Average: 523.55
Monoisotopic: 523.029011429
Chemical Formula
C19H17N5O7S3
Synonyms
  • Ceftiofur
  • Ceftiofur crystalline free acid

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

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.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Ceftiofur is combined with Acenocoumarol.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Ceftiofur.
DicoumarolThe risk or severity of bleeding can be increased when Ceftiofur is combined with Dicoumarol.
EstetrolThe therapeutic efficacy of Estetrol can be decreased when used in combination with Ceftiofur.
FluindioneThe risk or severity of bleeding can be increased when Ceftiofur is combined with Fluindione.
LactuloseThe therapeutic efficacy of Lactulose can be decreased when used in combination with Ceftiofur.
PhenindioneThe risk or severity of bleeding can be increased when Ceftiofur is combined with Phenindione.
PhenprocoumonThe risk or severity of bleeding can be increased when Ceftiofur is combined with Phenprocoumon.
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Ceftiofur.
Typhoid vaccineThe therapeutic efficacy of Typhoid vaccine can be decreased when used in combination with Ceftiofur.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ceftiofur hydrochloride6822A07436103980-44-5KEQFDTJEEQKVLM-JUODUXDSSA-N
Ceftiofur sodiumNHI34IS56E104010-37-9RFLHUYUQCKHUKS-JUODUXDSSA-M

Categories

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 / Furoic acid and derivatives / 2,4-disubstituted thiazoles / 2-amino-1,3-thiazoles / 1,3-thiazines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azetidines / Thioesters / Amino acids
show 14 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 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
83JL932I1C
CAS number
80370-57-6
InChI Key
ZBHXIWJRIFEVQY-IHMPYVIRSA-N
InChI
InChI=1S/C19H17N5O7S3/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28)/b23-11-/t12-,16-/m1/s1
IUPAC Name
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(furan-2-carbonylsulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(CSC(=O)C3=CC=CO3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O

References

General References
Not Available
KEGG Drug
D07657
ChemSpider
4886668
BindingDB
50103524
RxNav
1311521
ChEMBL
CHEMBL222913
ZINC
ZINC000004215267
Wikipedia
Ceftiofur

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.105 mg/mLALOGPS
logP1.22ALOGPS
logP-0.43ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area177.42 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity124.51 m3·mol-1ChemAxon
Polarizability49.83 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0403-0790000000-30fbbe814039d05b57ba

Drug created at February 25, 2016 20:35 / Updated at February 21, 2021 18:53