(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 1383
• Molecular Formular: C10H12N4O5S
• Molecular Mass: 300.29108
• Monoisotopic Mass: 300.0528405
• SMILES: S1(=O)(=O)[C@]([C@@H](N2[C@H]1CC2=O)C(=O)O)(Cn1nncc1)C
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)C[C@H]2S(=O)(=O)[C@@]1(C)Cn1ccnn1
• InChI: InChI=1S/C10H12N4O5S/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)/t7-,8+,10+/m1/s1
• InChIKey: LPQZKKCYTLCDGQ-WEDXCCLWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: tazobactamum
• Synonyms: Tazobactam

Database IDs

• CAS Number: 89786-04-9
• PubChem SID: 160964843; 46508088
• PubChem CID: 123630

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.8620825
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -3.9903479
• LogD (pH = 7.4): -4.8887963
• Log P: -1.3995085
• Molar Refractivity: 74.8153 cm^3
• Polarizability: 25.784103 Å^3
• Polar Surface Area: 122.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.8
• LOG S: -1.5
• Solubility (Water): 9.59e+00 g/l

DETAILS

DrugBank - DB01606

• Drug Groups: approved
• Description: Tazobactam is a antibacterial penicillin derivative which inhibits the action of bacterial beta-lactamases.
• Indication: Used in combination with piperacillin to broaden the spectrum of piperacillin antibacterial action.
• Pharmacology: Tazobactam is a compound which inhibits the action of bacterial beta-lactamases. It is added to the extended spectrum beta-lactam antibiotic piperacillin.
• Affected Organisms: Enteric bacteria and other eubacteria
• External Links: Wikipedia