(6R,7R)-3-[(acetyloxy)methyl]-7-[(2R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 571
• Molecular Formular: C18H19N3O6S
• Molecular Mass: 405.42496
• Monoisotopic Mass: 405.09945634
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](N)c2ccccc2)C(=C(C1)COC(=O)C)C(=O)O
• Canonical SMILES: CC(=O)OCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)[C@@H](c1ccccc1)N
• InChI: InChI=1S/C18H19N3O6S/c1-9(22)27-7-11-8-28-17-13(16(24)21(17)14(11)18(25)26)20-15(23)12(19)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1
• InChIKey: FUBBGQLTSCSAON-PBFPGSCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-[(acetyloxy)methyl]-7-[(2R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cephaloglycin
• Brand Name: CEG; Cefaloglicina [INN-Spanish]; Cefaloglycin; Cefaloglycine [INN-French]; Cefaloglycinum [INN-Latin]; Cephaloglycin anhydrous; Cephaloglycine; Cephaoglycin acid; D-Cephaloglycine; Kafocin; Kefglycin
• Synonyms: Cephaloglycin

Database IDs

• CAS Number: 3577-01-3
• PubChem SID: 46506850; 160964034
• PubChem CID: 19150

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3389544
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.9821522
• LogD (pH = 7.4): -3.236588
• Log P: -2.9842465
• Molar Refractivity: 99.8998 cm^3
• Polarizability: 39.14402 Å^3
• Polar Surface Area: 139.03 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.54
• LOG S: -3.44
• Solubility (Water): 1.48e-01 g/l

PROPERTIES

Physical Property

• Solubility: 154 mg/L
• Hydrophobicity(logP): -0.3

DETAILS

DrugBank - DB00689

• Drug Groups: approved
• Description: A cephalorsporin antibiotic. [PubChem]
• Indication: For treatment of severe infections caused by susceptible bacteria.
• Pharmacology: Cephaloglycin is an antibiotic related to cephalosporin but no longer in common use. It is an orally absorbed derivative of cephalosporin C.
• Toxicity: Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Well absorbed following oral administration.
• References: Tune BM, Hsu CY: The renal mitochondrial toxicity of beta-lactam antibiotics: in vitro effects of cephaloglycin and imipenem. J Am Soc Nephrol. 1990 Nov;1(5):815-21. [Pubmed] ; Tune BM, Fravert D, Hsu CY: Oxidative and mitochondrial toxic effects of cephalosporin antibiotics in the kidney. A comparative study of cephaloridine and cephaloglycin. Biochem Pharmacol. 1989 Mar 1;38(5):795-802. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Tune BM, Hsu CY: The renal mitochondrial toxicity of beta-lactam antibiotics: in vitro effects of cephaloglycin and imipenem. J Am Soc Nephrol. 1990 Nov;1(5):815-21. Pubmed
• Tune BM, Fravert D, Hsu CY: Oxidative and mitochondrial toxic effects of cephalosporin antibiotics in the kidney. A comparative study of cephaloridine and cephaloglycin. Biochem Pharmacol. 1989 Mar 1;38(5):795-802. Pubmed