1-[(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carbonyloxy]ethyl acetate

• ChemBase ID: 163951
• Molecular Formular: C20H22N4O10S
• Molecular Mass: 510.47448
• Monoisotopic Mass: 510.10566392
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC=C(C2C(=O)OC(C)OC(=O)C)COC(=O)N)NC(=O)/C(=N\OC)/c1ccco1
• Canonical SMILES: CO/N=C(/c1ccco1)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SC=C(C2C(=O)OC(OC(=O)C)C)COC(=O)N
• InChI: InChI=1S/C20H22N4O10S/c1-9(25)33-10(2)34-19(28)15-11(7-32-20(21)29)8-35-18-14(17(27)24(15)18)22-16(26)13(23-30-3)12-5-4-6-31-12/h4-6,8,10,14-15,18H,7H2,1-3H3,(H2,21,29)(H,22,26)/b23-13-/t10?,14-,15?,18-/m1/s1
• InChIKey: AQVGUOHUYICCIZ-WDVFJNCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carbonyloxy]ethyl acetate
• IUPAC Traditional name: 1-[(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carbonyloxy]ethyl acetate
• Synonyms: (6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic Acid 1-(Acetyloxy)ethyl Ester; Δ2-Cefuroxime Axetil

Database IDs

• CAS Number: 123458-61-7
• PubChem SID: 162258086
• PubChem CID: 71314630

CALCULATED PROPERTIES

• Acid pKa: 10.948226
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.7586381
• LogD (pH = 7.4): -0.7587455
• Log P: -0.75863665
• Molar Refractivity: 115.7469 cm^3
• Polarizability: 45.71708 Å^3
• Polar Surface Area: 189.06 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C248070

It is an oral prodrug of Cefuroxime (C248060), an injectable second generation cephalosporin with an excellent antibacterial activity. This ester is applied in therapy as a mixture of the R and S diastereoisomers.

REFERENCES

• Nguyen, N., et al.: Pharm. Res., 8, 893 (1991)
• Stoeckel, K., et al.: Antimicrob. Agents Chemother., 42, 2602 (1991)
• Scott, L., et al.: Drugs, 61, 1455 (1991)