Ceftiofur hydrochlorideProduct ingredient for Ceftiofur

Name
Ceftiofur hydrochloride
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
DBSALT001643
Structure
Synonyms
Ceftiofur HCl
UNII
6822A07436
CAS Number
103980-44-5
Weight
Average: 560.01
Monoisotopic: 559.0056892
Chemical Formula
C19H18ClN5O7S3
InChI Key
KEQFDTJEEQKVLM-JUODUXDSSA-N
InChI
InChI=1S/C19H17N5O7S3.ClH/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);1H/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 hydrochloride
SMILES
Cl.[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
KEGG Drug
D03430
ChemSpider
8113312
ChEMBL
CHEMBL2106486
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