sodium (2S,5R)-3-(2H3)methyl-3-methyl-4,4,7-trioxo(6,6-2H2)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 178007
• Molecular Formular: C8H10NNaO5S
• Molecular Mass: 255.22347
• Monoisotopic Mass: 255.01773771
• SMILES: C1C(=O)N2[C@@H]1S(=O)(=O)C([C@@H]2C(=O)[O-])(C)C.[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)C1(C)C.[Na+]
• InChI: InChI=1S/C8H11NO5S.Na/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14;/h5-6H,3H2,1-2H3,(H,11,12);/q;+1/p-1/t5-,6+;/m1./s1
• InChIKey: NKZMPZCWBSWAOX-IBTYICNHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R)-3-(^2H₃)methyl-3-methyl-4,4,7-trioxo(6,6-^2H₂)-4λ^6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium (2S,5R)-3-(^2H₃)methyl-3-methyl-4,4,7-trioxo(6,6-^2H₂)-4λ^6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: (2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid-d5 4,4-Dioxide Sodium Salt; CP 45899-2-d5; Penicillanic Acid-d5 1,1-Dioxide Sodium Salt; Sodium 1,1-Dioxypenicillanate-d5; Sodium Penicillanate-d5 1,1-Dioxide; Sodium Sulbactam-d5; Sulbactam-d5 Sodium; Sulbactam-d5 Sodium Salt; Unasyn IM-d5; Sulbactam-d5 Sodium Salt (Major)

Database IDs

• PubChem SID: 164233917
• PubChem CID: 71752295

CALCULATED PROPERTIES

• Acid pKa: 3.0900245
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -3.271277
• LogD (pH = 7.4): -4.3542833
• Log P: -0.8914056
• Molar Refractivity: 59.0516 cm^3
• Polarizability: 20.060627 Å^3
• Polar Surface Area: 94.58 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S699187

Labelled Sulbactam (S699185). A semi-synthetic β-lactamase inhibitor. It is used in combination with β-lactam antibiotics as antibacterial.

REFERENCES

• English, A.R., et al.: Antimicrob. Agents Chemother., 14, 414 (1978)
• Stromberg, B.V., Surg. Gynecol. Obstet., 162, 575 (1978)
• Mehtar, S., et al.: J. Antimicrob. Chemother., 17, 389 (1978)
• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1978)