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

• ChemBase ID: 1223
• Molecular Formular: C13H13N3O6S
• Molecular Mass: 339.32382
• Monoisotopic Mass: 339.05250615
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)CC#N)C(=C(C1)COC(=O)C)C(=O)O
• Canonical SMILES: CC(=O)OCC1=C(N2[C@H](SC1)[C@@H](C2=O)NC(=O)CC#N)C(=O)O
• InChI: InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
• InChIKey: RRYMAQUWDLIUPV-BXKDBHETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefacetrile
• Brand Name: Celospor; Celtol; Cristacef
• Synonyms: (6R,7R)-3-[(Acetyloxy)methyl]-7-[(2-cyanoacetyl)amino]-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-(2-Cyanoacetamido)-3-(hydroxymethyl)-8-oxo-5-thia--1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Acetate (Ester); 7-Cyanoacetamidocephalosporanic Acid; Cephacetril; Cephacetrile; Cefacetrilum [inn-latin]; Cefacetrilo [inn-spanish]; 7-Cyanacetylamino-cephalosporansaeure; Cefacetrile

Database IDs

• CAS Number: 10206-21-0
• PubChem SID: 160964683; 46504767
• PubChem CID: 91562

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3054466
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -4.022756
• LogD (pH = 7.4): -5.9693847
• Log P: -1.780771
• Molar Refractivity: 77.5056 cm^3
• Polarizability: 29.896023 Å^3
• Polar Surface Area: 136.8 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.52
• LOG S: -2.15
• Solubility (Water): 2.43e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Beige Solid
• Melting Point: 133-135°C
• Hydrophobicity(logP): -0.45 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB01414

• Drug Groups: approved
• Description: A derivative of 7-aminocephalosporanic acid.
• Indication: Cefacetrile is a broad-spectrum first generation cephalosporin antibiotic effective in Gram-positive and Gram-negative bacterial infections.
• Pharmacology: Cefacetrile is effective against many Gram-positive bacterial strains and somewhat less effective against Gram-negative species. It works by inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine.
• Affected Organisms: Enteric bacteria and other eubacteria
• Half Life: 1.2 hours
• Protein Binding: 23 to 38%
• Distribution: Vd of 0.2 to 0.5L/.kg
• External Links: Wikipedia

Toronto Research Chemicals - C231500

A cephalosporin antibiotic. Antibacterial.

REFERENCES

• Dajan, A., et al.: Vet. Microbiol., 35, 213 (1993)
• Becker, M., et al.: Anal. Chim. Acta, 520, 19 (1993)
• El-Shaboury, S., et al.: J. Pharm. Biomed. Anal., 45, 1 (1993)