1-[(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-[(2H3)methoxyimino]acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]ethyl acetate

• ChemBase ID: 163950
• Molecular Formular: C20H22N4O10S
• Molecular Mass: 510.47448
• Monoisotopic Mass: 510.10566392
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=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]1SCC(=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/h4-6,10,14,18H,7-8H2,1-3H3,(H2,21,29)(H,22,26)/b23-13-/t10?,14-,18-/m1/s1
• InChIKey: KEJCWVGMRLCZQQ-YJBYXUATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-[(^2H₃)methoxyimino]acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]ethyl acetate
• IUPAC Traditional name: 1-[(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-[(^2H₃)methoxyimino]acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]ethyl acetate
• Synonyms: (6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxy-d3-imino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid 1-(Acetyloxy)ethyl Ester; Altacef-d3; Bioracef-d3; CCI 15641-d3; Cefaks-d3; Cefazine-d3; Ceftin-d3; Cefurax-d3; Cefuroxime-d3 1-Acetoxyethyl Ester; Elobact-d3; Forcef-d3; Oraxim-d3; Zinat-d3; Zinnat-d3; Cefuroxime Axetil-d3

Database IDs

• PubChem SID: 162258085
• PubChem CID: 71314629

CALCULATED PROPERTIES

• Acid pKa: 10.924807
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.43309042
• LogD (pH = 7.4): -0.43320468
• Log P: -0.43308887
• Molar Refractivity: 117.0305 cm^3
• Polarizability: 45.711346 Å^3
• Polar Surface Area: 189.06 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C248067

Labelled Cefuroxime Axetil (C248065). It is the 1-(acetyloxy) ethyl ester of Cefuroxime (C248060), an injectable second generation cephalosporin with an excellent antibacterial activity. This ester has a broader spectrum of activity than cephalexin (first

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)
• Bulitta, J. B., et al.: Antimicrob. Agents Chemother., 53, 3462 (1991)