sodium (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 155656
• Molecular Formular: C10H11N4NaO5S
• Molecular Mass: 322.27291
• Monoisotopic Mass: 322.03478475
• SMILES: C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)[O-])Cn1ccnn1.[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)[C@@]1(C)Cn1ccnn1.[Na+]
• InChI: InChI=1S/C10H12N4O5S.Na/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19;/h2-3,7-8H,4-5H2,1H3,(H,16,17);/q;+1/p-1/t7-,8+,10+;/m1./s1
• InChIKey: RFMIKMMOLPNEDG-QVUDESDKSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4λ^6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1,2,3-triazol-1-ylmethyl)-4λ^6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: CL-298741; YTR-830H; [2S-(2α, 3β, 5α)]-3-Methyl-7-oxo-3(1H,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide; Tazobactam sodium salt; (2S,3S,5R)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid 4,4-dioxide Sodium Salt; YTR-830; CL-307579; Tazobactam Sodium Salt

Database IDs

• CAS Number: 89785-84-2
• MDL Number: MFCD00917472
• PubChem SID: 162249794
• PubChem CID: 23663400

CALCULATED PROPERTIES

• Acid pKa: 2.8620825
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): -3.9903479
• LogD (pH = 7.4): -4.8887963
• Log P: -1.3995085
• Molar Refractivity: 85.6524 cm^3
• Polarizability: 25.66645 Å^3
• Polar Surface Area: 125.29 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless; Methanol; Water
• Apperance: White Solid
• Melting Point: >150°C dec.

Safety Information

• Storage Condition: Refrigerator
• RTECS: XI0191500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C10H11N4NaO5S

DETAILS

Sigma Aldrich - T2820

Biochem/physiol Actions
Tazobactam is a β -Lactamase inhibitor. When used with β-lactam antibiotics I, it enhances their effect.
Application
Tazobactam is an antibacterial penicillin derivative which inhibits the action of bacterial β-lactamases. It is used in combination with piperacillin and other β-lactam antibiotics to broaden their spectrum and enhance their effect1,2. It is used for bacterial β-lactamase and penicillinase inhibition studies.

Toronto Research Chemicals - T010100

β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.

REFERENCES

• Gould, I.M., et al.: Drugs Exp. Clin. Res., 17, 187 (1991)
• Roland, R.K., et al.: J. Infect. Dis., 4, 226 (1991)
• Bonomo, R.A., et al.: Biochim. Biophys. Acta, 1547, 196 (1991)