sodium (5R)-6-{5H,6H,8H-imidazo[2,1-c][1,4]oxazin-3-ylmethylidene}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

• ChemBase ID: 162450
• Molecular Formular: C13H10N3NaO4S
• Molecular Mass: 327.29097
• Monoisotopic Mass: 327.0289711
• SMILES: C1OCc2n(C1)c(cn2)/C=C/1\[C@@H]2N(C1=O)C(=CS2)C(=O)[O-].[Na+]
• Canonical SMILES: O=C1/C(=C/c2cnc3n2CCOC3)/[C@@H]2N1C(=CS2)C(=O)[O-].[Na+]
• InChI: InChI=1S/C13H11N3O4S.Na/c17-11-8(12-16(11)9(6-21-12)13(18)19)3-7-4-14-10-5-20-2-1-15(7)10;/h3-4,6,12H,1-2,5H2,(H,18,19);/q;+1/p-1/b8-3-;/t12-;/m1./s1
• InChIKey: KQYPOKARFSWFMK-ZDFSRXSCSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (5R)-6-{5H,6H,8H-imidazo[2,1-c][1,4]oxazin-3-ylmethylidene}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• IUPAC Traditional name: sodium (5R)-6-{5H,6H,8H-imidazo[2,1-c][1,4]oxazin-3-ylmethylidene}-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• Synonyms: (5R,6Z)-6-[(5,6-Dihydro-8H-imidazo[2,1-c][1,4]oxazin-2-yl)methylene]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid Sodium Salt Hydrate; BLI 489 Hydrate

Database IDs

• CAS Number: 623564-40-9
• PubChem SID: 162256585
• PubChem CID: 71314126

CALCULATED PROPERTIES

• Acid pKa: 3.7518432
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -2.2635782
• LogD (pH = 7.4): -3.758194
• Log P: -2.0656204
• Molar Refractivity: 86.8934 cm^3
• Polarizability: 28.39123 Å^3
• Polar Surface Area: 87.49 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B595825

BLI-489 is a penem β-lactamase inhibitor, which has shown activity against class A, C, and D β-lactamases. BLI-489 is being tested in combination therapy for drug-resistant bacteria.

REFERENCES

• Maiti, S., et al.: Curr. Med. Chem., 5, 441 (1998)
• Barnaud, G., et al.: Antimicrob. Agents Chemother., 48, 1040 (1998)
• Szabo, D., et al.: J. Clin. Microbiol., 43, 5058 (1998)