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

• ChemBase ID: 163913
• Molecular Formular: C16H15N5O7S2
• Molecular Mass: 453.4496
• Monoisotopic Mass: 453.04128985
• SMILES: S1[C@H]2N(C(=C(C1)C=C)C(=O)O)C(=O)[C@@H]2NC(=O)/C(=N\OCC(=O)O)/c1csc(n1)N
• Canonical SMILES: Nc1nc(cs1)/C(=N/OCC(=O)O)/C(=O)N[C@@H]1[C@H]2SCC(=C(N2C1=O)C(=O)O)C=C
• InChI: InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14+/m0/s1
• InChIKey: OKBVVJOGVLARMR-WVIRHPHLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 108691-83-4
• PubChem SID: 162258048
• PubChem CID: 71314611

CALCULATED PROPERTIES

• Acid pKa: 3.4486887
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -4.517875
• LogD (pH = 7.4): -7.089293
• Log P: -1.5863124
• Molar Refractivity: 104.9118 cm^3
• Polarizability: 39.59456 Å^3
• Polar Surface Area: 184.51 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C242815

7-epi-Cefixime is an epimeric impurity of the third generation cephalosporin antibiotic, Cefixime (C242800).

REFERENCES

• Namiki, Y. et al.: J. Pharmac. Sci., 76, 208 (1987)