[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate

• ChemBase ID: 163906
• Molecular Formular: C20H25N5O7S2
• Molecular Mass: 511.5718
• Monoisotopic Mass: 511.11954017
• SMILES: S1[C@H]2N(C(=C(C1)C)C(=O)OCOC(=O)C(C)(C)C)C(=O)[C@H]2NC(=O)/C(=N\OC)/c1csc(n1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)OCOC(=O)C(C)(C)C)C
• InChI: InChI=1S/C20H25N5O7S2/c1-9-6-33-16-12(23-14(26)11(24-30-5)10-7-34-19(21)22-10)15(27)25(16)13(9)17(28)31-8-32-18(29)20(2,3)4/h7,12,16H,6,8H2,1-5H3,(H2,21,22)(H,23,26)/b24-11-/t12-,16-/m1/s1
• InChIKey: DASYMCLQENWCJG-XUKDPADISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• Synonyms: [2R-[2α,6α,7β(Z)]]-7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic Acid (2,2-Dimethyl-1-oxopropoxy)methyl Ester; Δ2-Cefetamet Pivoxil (Contain 20% Cefetamet Pivoxil)

Database IDs

• CAS Number: 126617-54-7
• PubChem SID: 162258041
• PubChem CID: 5486182

CALCULATED PROPERTIES

• Acid pKa: 10.942633
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 2.131545
• LogD (pH = 7.4): 2.14948
• Log P: 2.1498265
• Molar Refractivity: 122.9069 cm^3
• Polarizability: 47.570835 Å^3
• Polar Surface Area: 162.51 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C242775

Δ2-Isomer of Cefetamet Pivoxil (C242780) as a prodrug.

REFERENCES

• Miyauchi, M., et al.: Chem. Pharma. Bull., 37, 3272 (1989)