(6R,7R)-7-{2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido}-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 1163
• Molecular Formular: C25H27N9O8S2
• Molecular Mass: 645.66738
• Monoisotopic Mass: 645.14240087
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)C(NC(=O)N2CCN(C(=O)C2=O)CC)c2ccc(O)cc2)C(=C(C1)CSc1n(nnn1)C)C(=O)O
• Canonical SMILES: CCN1CCN(C(=O)C1=O)C(=O)NC(c1ccc(cc1)O)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C
• InChI: InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15?,16-,22-/m1/s1
• InChIKey: GCFBRXLSHGKWDP-WTKTZPJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-{2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido}-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[2-(4-ethyl-2,3-dioxopiperazine-1-carbonylamino)-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Brand Name: Cefobid
• Synonyms: Cefoperazono [inn-spanish]; Cefoperazonum [inn-latin]; Cefoperazone

Database IDs

• CAS Number: 62893-19-0
• PubChem SID: 160964626; 46504543
• PubChem CID: 44185

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3837204
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -3.0036721
• LogD (pH = 7.4): -4.3111243
• Log P: -0.9004894
• Molar Refractivity: 169.0571 cm^3
• Polarizability: 59.325363 Å^3
• Polar Surface Area: 220.26 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.11
• LOG S: -3.35
• Solubility (Water): 2.86e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.74 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB01329

• Drug Groups: approved
• Description: Semisynthetic broad-spectrum cephalosporin with a tetrazolyl moiety that is resistant to beta-lactamase. It has been proposed especially against Pseudomonas infections.
• Indication: For the treatment of bacterial infections caused by susceptible microorganisms.
• Pharmacology: Cefoperazone is a third generation cephalosporin antibiotic. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis
• Toxicity: Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: No significant quanitity of metabolites have been identified in urine.
• Half Life: The mean serum half-life is approximately 2.0 hours, independent of the route of administration.
• Protein Binding: The degree of reversible protein binding varies with the serum concentration from 93% at 25 mcg/mL to 90% at 250 mcg/mL and 82% at 500 mcg/mL. Cefotetan is 88% plasma protein bound.
• Elimination: Cefoperazone is excreted mainly in the bile.
• References: Jones RN, Barry AL: Cefoperazone: a review of its antimicrobial spectrum, beta-lactamase stability, enzyme inhibition, and other in vitro characteristics. Rev Infect Dis. 1983 Mar-Apr;5 Suppl 1:S108-26. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Jones RN, Barry AL: Cefoperazone: a review of its antimicrobial spectrum, beta-lactamase stability, enzyme inhibition, and other in vitro characteristics. Rev Infect Dis. 1983 Mar-Apr;5 Suppl 1:S108-26. Pubmed