(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

• ChemBase ID: 163941
• Molecular Formular: C19H17N5O7S3
• Molecular Mass: 523.56258
• Monoisotopic Mass: 523.02901091
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSC(=O)c1occc1)NC(=O)/C(=N\OC)/c1nc(sc1)N
• 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
• 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
• InChIKey: ZBHXIWJRIFEVQY-IHMPYVIRSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: ceftiofur
• Synonyms: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(2-furanylcarbonyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; CM 31916; Excede; CeftiofurSee C244700; [6R-[6α,7β(Z)]]-7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(2-furanylcarbonyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

Database IDs

• CAS Number: 80370-57-6
• PubChem SID: 162258076
• PubChem CID: 6328657

CALCULATED PROPERTIES

• Acid pKa: 2.8336952
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.4857522
• LogD (pH = 7.4): -2.4443562
• Log P: -0.42835948
• 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

DETAILS

Toronto Research Chemicals - C244695

A third generation cephalosporin antibiotic for used in veterinary medicine. It is resistant to antibiotic resistance enzyme beta-lactamase.

REFERENCES

• Donaldson, S.C. et al.: Appl. Environ. Microbiol., 72, 3940 (2006)
• Yancey, R.J. et al.: Am. J. Vet. Res., 48, 1050 (2006)