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

• ChemBase ID: 163936
• Molecular Formular: C23H24N6O7S2
• Molecular Mass: 560.60266
• Monoisotopic Mass: 560.11478914
• SMILES: [C@@H]12N(C(=C(CS1)C[n+]1ccccc1)C(=O)[O-])C(=O)[C@H]2NC(=O)/C(=N\OC(C(=O)OC)(C)C)/c1nc(sc1)N
• Canonical SMILES: COC(=O)C(O/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[n+]1ccccc1)(C)C
• InChI: InChI=1S/C23H24N6O7S2/c1-23(2,21(34)35-3)36-27-14(13-11-38-22(24)25-13)17(30)26-15-18(31)29-16(20(32)33)12(10-37-19(15)29)9-28-7-5-4-6-8-28/h4-8,11,15,19H,9-10H2,1-3H3,(H3-,24,25,26,30,32,33)/b27-14-/t15-,19-/m1/s1
• InChIKey: SQQLCFFMLJEMPT-CDOVDWRASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(1-methoxy-2-methyl-1-oxopropan-2-yl)oxy]imino}acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-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-methoxy-2-methyl-1-oxopropan-2-yl)oxy]imino}acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium
• Synonyms: 1-[[(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-[[2-(methoxy)-1,1-dimethyl-2-oxoethoxy]imino]acetyl]amino]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium Inner Salt; Ceftazidime Methyl Ester

Database IDs

• PubChem SID: 162258071
• PubChem CID: 71314621

CALCULATED PROPERTIES

• Acid pKa: 2.9061513
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -3.4566865
• LogD (pH = 7.4): -3.4443963
• Log P: -4.3318205
• Molar Refractivity: 148.65 cm^3
• Polarizability: 52.434628 Å^3
• Polar Surface Area: 180.22 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C244120

Ceftazidime Methyl ester is an impurity of Ceftazidime (C244100). Ceftazidime impurity G.

REFERENCES

• Miyake, A., et al.: Antimicrob. Agents Chemother., 486, 182 (1989)
• Seibert, G., et al.: Arzneim.-Forsch., 33, 1084 (1989)