(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(2-ethoxy-2-oxoethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 163914
• Molecular Formular: C18H19N5O7S2
• Molecular Mass: 481.50276
• Monoisotopic Mass: 481.07258997
• SMILES: S1[C@H]2N(C(=C(C1)C=C)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\OCC(=O)OCC)/c1csc(n1)N
• Canonical SMILES: CCOC(=O)CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)C=C
• InChI: InChI=1S/C18H19N5O7S2/c1-3-8-6-31-16-12(15(26)23(16)13(8)17(27)28)21-14(25)11(9-7-32-18(19)20-9)22-30-5-10(24)29-4-2/h3,7,12,16H,1,4-6H2,2H3,(H2,19,20)(H,21,25)(H,27,28)/b22-11-/t12-,16-/m1/s1
• InChIKey: QVMFLNUARRRNPY-WGHMCSAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(2-ethoxy-2-oxoethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(2-ethoxy-2-oxoethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: Cefixime Ethyl Ester (Cefixime EP Impurity F); (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-[(2-ethoxy-2-oxoethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; [6R-[6α,7β(Z)]]-7-[[(2-Amino-4-thiazolyl)[(2-ethoxy-2-oxoethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

Database IDs

• CAS Number: 79368-95-9
• PubChem SID: 162258049
• PubChem CID: 14634186

CALCULATED PROPERTIES

• Acid pKa: 3.21517
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.966753
• LogD (pH = 7.4): -3.1952455
• Log P: -0.8653012
• Molar Refractivity: 114.4295 cm^3
• Polarizability: 43.450176 Å^3
• Polar Surface Area: 173.51 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C242830

Cefixime Ethyl Ester is an ester impurity of the third generation cephalosporin antibiotic, Cefixime (C242800).

REFERENCES

• Bian, L. et al.: Yao. Fen. Zaz., 30, 872 (2010)