1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl}pyridin-1-ium

• ChemBase ID: 163934
• Molecular Formular: C22H22N6O7S2
• Molecular Mass: 546.57608
• Monoisotopic Mass: 546.09913907
• SMILES: [C@@H]12N(C(C(=CS1)C[n+]1ccccc1)C(=O)[O-])C(=O)[C@H]2NC(=O)/C(=N\OC(C)(C)C(=O)O)/c1nc(sc1)N
• Canonical SMILES: [O-]C(=O)C1C(=CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N\OC(C(=O)O)(C)C)/c1csc(n1)N)C[n+]1ccccc1
• InChI: InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,9-10,14-15,18H,8H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,15?,18-/m1/s1
• InChIKey: LRKHKETXQNDOKF-YTAHGSIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl}pyridin-1-ium
• IUPAC Traditional name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl}pyridin-1-ium
• Synonyms: 1-[[(2R,6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl]pyridinium; Δ2-Ceftazidime

Database IDs

• CAS Number: 217796-42-4
• PubChem SID: 162258069
• PubChem CID: 23659635

CALCULATED PROPERTIES

• Acid pKa: 2.5048652
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -5.6234317
• LogD (pH = 7.4): -7.0349703
• Log P: -4.718341
• Molar Refractivity: 142.5973 cm^3
• Polarizability: 50.384262 Å^3
• Polar Surface Area: 191.22 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C244110

A Ceftazidime isomer, an impurity of Ceftazidime (C244100).

REFERENCES

• Vilanova, B., et al.: Helv. Chim. Acta, 76, 2789 (1993)
• Zhou, M., et al.: J. Pharm. Sci., 84, 534 (1993)
• Baertschi, S., et al.: Chemother. 8, 353 (1993)
• Porra, R., et al.: J. Pharm. Biomed. Anal., 18, 241 (1993)