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

• ChemBase ID: 1162
• Molecular Formular: C18H18N6O8S3
• Molecular Mass: 542.56592
• Monoisotopic Mass: 542.03482457
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)C(O)c2ccccc2)C(=C(C1)CSc1n(nnn1)CS(=O)(=O)O)C(=O)O
• Canonical SMILES: O=C(C(c1ccccc1)O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1CS(=O)(=O)O
• InChI: InChI=1S/C18H18N6O8S3/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)/t11-,13?,16-/m1/s1
• InChIKey: DYAIAHUQIPBDIP-UJBKNGIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-(2-hydroxy-2-phenylacetamido)-8-oxo-3-({[1-(sulfomethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: monocef
• Brand Name: Monocid; Praticef
• Synonyms: Cefonicido [inn-spanish]; Cefonicidum [inn-latin]; Cefonicid

Database IDs

• CAS Number: 61270-58-4
• PubChem SID: 160964625
• PubChem CID: 43592

CALCULATED PROPERTIES

JChem

• Acid pKa: -1.404536
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -5.733945
• LogD (pH = 7.4): -6.8324103
• Log P: -2.5153315
• Molar Refractivity: 136.5757 cm^3
• Polarizability: 48.276943 Å^3
• Polar Surface Area: 204.91 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.71
• LOG S: -2.78
• Solubility (Water): 8.95e-01 g/l

DETAILS

DrugBank - DB01328

• Drug Groups: approved
• Description: A second-generation cephalosporin administered intravenously or intramuscularly. Its bactericidal action results from inhibition of cell wall synthesis. It is used for urinary tract infections, lower respiratory tract infections, and soft tissue and bone infections. [PubChem]
• Indication: For the treatment of bacterial infections caused by susceptible microorganisms.
• Pharmacology: Cefonicid is a second-generation cephalosporin administered intravenously or intramuscularly. Its bactericidal action results from inhibition of cell wall synthesis. It is used for urinary tract infections, lower respiratory tract infections, and soft tissue and bone infections.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Not metabolized.
• Half Life: 4.5 hours
• Protein Binding: 98% bound to plasma proteins.