disodium (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-8-oxo-3-({[1-(sulfonatomethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 163916
• Molecular Formular: C18H16N6Na2O8S3
• Molecular Mass: 586.52958
• Monoisotopic Mass: 585.99871306
• SMILES: S1[C@H]2N(C(=C(C1)CSc1nnnn1CS(=O)(=O)[O-])C(=O)[O-])C(=O)[C@H]2NC(=O)[C@@H](c1ccccc1)O.[Na+].[Na+]
• Canonical SMILES: O=C([C@@H](c1ccccc1)O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])CSc1nnnn1CS(=O)(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C18H18N6O8S3.2Na/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32;;/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32);;/q;2*+1/p-2/t11-,13-,16-;;/m1../s1
• InChIKey: NAXFZVGOZUWLEP-RFXDPDBWSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-8-oxo-3-({[1-(sulfonatomethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: disodium cefonicid(2-)
• Synonyms: (6R,7R)-7-[[(2R)-2-Hydroxy-2-phenylacetyl]amino]-8-oxo-3-[[[1-(sulfomethyl)-1H-tetrazol-5-yl]thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Disodium Salt; Cefodie; Monocidur; Mopnocid; Praticef; Cefonicid Disodium Salt

Database IDs

• CAS Number: 190181-58-9
• PubChem SID: 162258051
• PubChem CID: 43593

CALCULATED PROPERTIES

• Acid pKa: -1.404536
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): -5.733945
• LogD (pH = 7.4): -6.8324103
• Log P: -2.5153315
• Molar Refractivity: 146.2911 cm^3
• Polarizability: 48.04395 Å^3
• Polar Surface Area: 210.57 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >230°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C242875

A semi-synthetic cephalosporin antibiotic related to Cefamandole. Antibacterial.

REFERENCES

• Actor, P., et al.: Antimicrob. Agents Chemother., 13, 784 (1978)
• Mehta, R., et al.: J. Antibiot., 34, 202 (1978)
• Pitkin, D., et al.: Clin. Pharmacol. Ther., 30, 587 (1978)
• Saltiel. E., et al.: Drugs, 32, 222 (1978)