(6R,7R)-7-[(2E)-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

• ChemBase ID: 73093
• Molecular Formular: C19H18ClN5O7S3
• Molecular Mass: 560.02352
• Monoisotopic Mass: 559.00568862
• SMILES: N12[C@H](SCC(=C1C(=O)O)CSC(=O)c1occc1)[C@@H](C2=O)NC(=O)/C(=N/OC)/c1nc(sc1)N.Cl
• Canonical SMILES: CO/N=C(\c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSC(=O)c1ccco1.Cl
• 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
• InChIKey: KEQFDTJEEQKVLM-BIDYTWAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2E)-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
• IUPAC Traditional name: (6R,7R)-7-[(2E)-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
• Synonyms: Ceftiofur hydrochloride

Database IDs

• CAS Number: 103980-44-5
• PubChem SID: 162038013
• PubChem CID: 9915819

CALCULATED PROPERTIES

• Acid pKa: 2.6681464
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.4816617
• LogD (pH = 7.4): -2.44558
• Log P: 0.22351335
• Molar Refractivity: 124.5146 cm^3
• Polarizability: 47.04454 Å^3
• Polar Surface Area: 177.42 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: hydrochloride

DETAILS

Selleck Chemicals - S2543

Research Area: Infection
Biological Activity:
Ceftiofur hydrochloride is a hydrochloride of ceftiofur that is a broad spectrum cephalosporin. Ceftiofur hydrochloride is resistant to the antibiotic resistance enzyme beta-lactamase. Ceftiofur hydrochloride has activity against Gram-positive and Gram-negative bacteria. E. coli strains resistant to ceftiofur have been reported. Ceftiofur was more active than was ampicillin against all strains tested including beta-lactamase-producing organisms. In mice with systemic infections, ceftiofur was more active than or equivalent to ampicillin, cephalothin, cefamandole, cloxacillin, cefoperazone, or pirlimycin. These protection tests included infections with Escherichia coli, Haemophilus pleuropneumoniae, H somnus, Pasteurella haemolytica, P multocida, Salmonella typhimurium, or Staphylococcus aureus. In infant mice with E coli-induced lethal diarrhea and in mice with S aureus and E coli-induced mastitis, ceftiofur was comparable or more active than was ampicillin. [1][2][3]

REFERENCES

• Yancey RJ Jr et al. Am J Vet Res. 1987 Jul; 48(7):1050-3.