(6R,7R)-7-[(2Z)-2-[2-amino(2-13C,3-15N)-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: 163910
• Molecular Formular: C16H15N5O7S2
• Molecular Mass: 456.42907263
• Monoisotopic Mass: 456.03871447
• SMILES: S1[C@H]2N(C(=C(C1)C=C)C(=O)O)C(=O)[C@H]2NC(=O)/C(=N\OCC(=O)O)/c1cs[13c]([15n]1)[15NH2]
• Canonical SMILES: [15NH2][13c]1[15n]c(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-/m1/s1/i16+1,17+1,18+1
• InChIKey: OKBVVJOGVLARMR-KNYKSROZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2Z)-2-[2-amino(2-^1^3C,3-^1^5N)-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,7R)-7-[(2Z)-2-[2-amino(2-^1^3C,3-^1^5N)-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: FK-027-13C,15N2; FR- 17027-13C,15N2; CL-284635-13C,15N2; Cefixoral-13C,15N2; Cefspan-13C,15N2; Cephoral-13C,15N2; Unixime-13C,15N2; Cefixime-13C,15N2; (6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl-13C,15N2)-2-[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

Database IDs

• PubChem SID: 162258045
• PubChem CID: 71314608

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 - C242802

Labelled Cefixime (C242800). Orally active, third generation cephalosporin antibiotic.

REFERENCES

• Kamimura, T., et al.: Antimicrob. Agents Chemother., 25, 98 (1984)
• Yamanaka, H., et al.: J. Antibiot., 38, 1738 (1984)
• Guay, D.R.P., et al.: Antimicrob. Agents Chemother., 30, 485 (1984)