Ceftiofur sodiumProduct ingredient for Ceftiofur

Name
Ceftiofur sodium
Drug Entry
Ceftiofur

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.

Accession Number
DBSALT001644
Structure
Thumb
Synonyms
Not Available
UNII
NHI34IS56E
CAS Number
104010-37-9
Weight
Average: 545.53
Monoisotopic: 545.01095568
Chemical Formula
C19H16N5NaO7S3
InChI Key
RFLHUYUQCKHUKS-JUODUXDSSA-M
InChI
InChI=1S/C19H17N5O7S3.Na/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);/q;+1/p-1/b23-11-;/t12-,16-;/m1./s1
IUPAC Name
sodium (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-carboxylate
SMILES
[Na+].[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
External Links
KEGG Drug
D01682
KEGG Compound
C13143
ChemSpider
7845539
ChEBI
31383
ChEMBL
CHEMBL2105998
Predicted Properties
PropertyValueSource
Water Solubility0.145 mg/mLALOGPS
logP1.63ALOGPS
logP-0.43ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)4.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area180.25 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity135.35 m3·mol-1ChemAxon
Polarizability49.3 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon