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

• ChemBase ID: 119446
• Molecular Formular: C8H11NO5S
• Molecular Mass: 233.24164
• Monoisotopic Mass: 233.03579346
• SMILES: S1(=O)(=O)C([C@@H](N2[C@H]1CC2=O)C(=O)O)(C)C
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)C1(C)C
• InChI: InChI=1S/C8H11NO5S/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)/t5-,6+/m1/s1
• InChIKey: FKENQMMABCRJMK-RITPCOANSA-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-carboxylic acid
• IUPAC Traditional name: sulbactam; (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ^6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: Sulbactam; (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide; Betamaze; CP 45899; CP-45,899; Penicillanic acid 1,1-dioxide; Penicillanic acid S,S-dioxide; Penicillanic acid dioxide; Penicillanic acid sulfone; Sulbactam; (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide; (2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4,4-Dioxide Sodium Salt; CP 45899-2; Penicillanic Acid 1,1-Dioxide Sodium Salt; Sodium 1,1-Dioxypenicillanate; Sodium Penicillanate 1,1-Dioxide; Sodium Sulbactam; Sulbactam Sodium; Sulbactam Sodium Salt; Unasyn IM; Sulbactam Sodium Salt; 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide; Antibiotic CP 45899

Database IDs

• CAS Number: 68373-14-8; 69388-84-7
• EC Number: 269-878-2
• MDL Number: MFCD00867005
• PubChem SID: 162107598
• PubChem CID: 130313

CALCULATED PROPERTIES

• Acid pKa: 3.0900245
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -3.271277
• LogD (pH = 7.4): -4.3542833
• Log P: -0.8914056
• Molar Refractivity: 48.2145 cm^3
• Polarizability: 20.178257 Å^3
• Polar Surface Area: 91.75 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥18 mg/mL; Methanol (Sparingly); Water
• Apperance: White Solid; white to tan powder
• Melting Point: >230°C (dec.)
• Optical Rotation: [α]/D ≥+225°, c = 1 in H2O
• Hydrophobicity(logP): 0.314

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others
• Mechanism of Action: Beta-Lactamase inhibitor; Inhibits beta-lactamases of the Richmond-Sykes types I; II; III; IV; V

Product Information

• Purity: ≥98% (HPLC); 95%
• Salt Data: Free Base
• Application(s): Antibiotic; Has only weak antibacterial activity except against Neisseria gonorrhoeae; Neisseria meningitidis
• Empirical Formula (Hill Notation): C8H11NO5S

DETAILS

Toronto Research Chemicals - S699185

A semi-synthetic β-lactamase inhibitor. It is used in combination with β-lactam antibiotics as antibacterial.

REFERENCES

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