(6R,7R)-7-{2-[(difluoromethyl)sulfanyl]acetamido}-3-({[1-(2-hydroxyethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 169000
• Molecular Formular: C15H18F2N6O7S2
• Molecular Mass: 496.4662264
• Monoisotopic Mass: 496.06464539
• SMILES: [C@@]1(C(=O)N2[C@@H]1OCC(=C2C(=O)O)CSc1nnnn1CCO)(NC(=O)CSC(F)F)OC
• Canonical SMILES: OCCn1nnnc1SCC1=C(C(=O)O)N2[C@H](OC1)[C@](C2=O)(OC)NC(=O)CSC(F)F
• InChI: InChI=1S/C15H18F2N6O7S2/c1-29-15(18-8(25)6-31-13(16)17)11(28)23-9(10(26)27)7(4-30-12(15)23)5-32-14-19-20-21-22(14)2-3-24/h12-13,24H,2-6H2,1H3,(H,18,25)(H,26,27)/t12-,15+/m1/s1
• InChIKey: UHRBTBZOWWGKMK-DOMZBBRYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-{2-[(difluoromethyl)sulfanyl]acetamido}-3-({[1-(2-hydroxyethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: flomoxef
• Synonyms: (6R,7R)-7-[[[(Difluoromethyl)thio]acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R-cis)7-[[[(Difluoromethyl)thio]acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; FMOX; Flomoxef

Database IDs

• CAS Number: 99665-00-6
• PubChem SID: 162263132
• PubChem CID: 65864

CALCULATED PROPERTIES

• Acid pKa: 3.2831113
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -2.3096263
• LogD (pH = 7.4): -3.5483587
• Log P: -0.11065078
• Molar Refractivity: 119.6599 cm^3
• Polarizability: 40.660442 Å^3
• Polar Surface Area: 169.0 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F401850

Flomoxef is an oxacephem derived beta-lactam antibiotic that is particularly effective against gram-positive bacteria.

REFERENCES

• Miwa, H. et al.: Chemotherapy, 35, 121 (1987)
• Mikamo, H. et al.: Curr. Therap. Res., 56, 873 (1987)