[(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate

• ChemBase ID: 178008
• Molecular Formular: C14H21NO7S
• Molecular Mass: 347.38404
• Monoisotopic Mass: 347.10387302
• SMILES: C1C(=O)N2[C@@H]1S(=O)(=O)C([C@@H]2C(=O)OCOC(=O)C(C)(C)C)(C)C
• Canonical SMILES: O=C([C@@H]1N2C(=O)C[C@H]2S(=O)(=O)C1(C)C)OCOC(=O)C(C)(C)C
• InChI: InChI=1S/C14H21NO7S/c1-13(2,3)12(18)22-7-21-11(17)10-14(4,5)23(19,20)9-6-8(16)15(9)10/h9-10H,6-7H2,1-5H3/t9-,10+/m1/s1
• InChIKey: OHPVYKXTRACOSQ-ZJUUUORDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ^6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: sulbactam pivoxil
• Synonyms: (2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (2,2-Dimethyl-1-oxopropoxy)methyl Ester 4,4-Dioxide; (Pivaloyloxy)methyl Penicillanate S,S-Dioxide; CP 47904; (2S-cis)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (2,2-dimethyl-1-oxopropoxy)methyl Ester 4,4-Dioxide; Sulbactam Pivoxil

Database IDs

• CAS Number: 69388-79-0
• PubChem SID: 164233918
• PubChem CID: 9997821

CALCULATED PROPERTIES

• Acid pKa: 18.590843
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.9151492
• LogD (pH = 7.4): 0.9151492
• Log P: 0.9151492
• Molar Refractivity: 76.9393 cm^3
• Polarizability: 32.209435 Å^3
• Polar Surface Area: 107.05 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S699190

Sulbactam Pivoxil is a prodrug of the semi-synthetic β-lactamase inhibitor Sulbactam (S699195).

REFERENCES

• Foulds, G. et al.: Curr. Chemother. Infect. Dis., Proc. Int. Congr. Chemother., 11, 353 (1980)
• Pei, Q. et al.: J. Chrom. B Anal. Technol. Biomed. Life Sci., 879, 2000 (1980)