1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium

• ChemBase ID: 1222
• Molecular Formular: C19H24N6O5S2
• Molecular Mass: 480.56106
• Monoisotopic Mass: 480.1249599
• SMILES: S1[C@H]2N(C(=C(C[N+]3(CCCC3)C)C1)C(=O)[O-])C(=O)[C@H]2NC(=O)/C(=N\OC)/c1nc(sc1)N
• Canonical SMILES: CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[N+]1(C)CCCC1
• InChI: InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1
• InChIKey: HVFLCNVBZFFHBT-ZKDACBOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}-1-methylpyrrolidin-1-ium
• IUPAC Traditional name: cefepime product
• Brand Name: Maxipime; Maxcef; Cepimax; Cepimex; Axepim
• Synonyms: Cefepima [spanish]; Cefepimum [latin]; Cefepime

Database IDs

• CAS Number: 88040-23-7
• PubChem SID: 160964682; 46507919
• PubChem CID: 5479537

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.9378078
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.454222
• LogD (pH = 7.4): -3.4482393
• Log P: -4.2875876
• Molar Refractivity: 141.9753 cm^3
• Polarizability: 45.275974 Å^3
• Polar Surface Area: 150.04 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.37
• LOG S: -4.49
• Solubility (Water): 1.73e-02 g/l

DETAILS

DrugBank - DB01413

• Drug Groups: approved
• Description: Cefepime is a fourth-generation cephalosporin antibiotic developed in 1994. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both Gram-negative and Gram-positive organisms than third-generation agents. Cefepime is usually reserved to treat severe nosocomial pneumonia, infections caused by multi-resistant microorganisms (e.g. Pseudomonas aeruginosa) and empirical treatment of febrile neutropenia.
• Indication: For the treatment of pneumonia (moderate to severe) caused by Streptococcus pneumoniae, including cases associated with concurrent bacteremia, Pseudomonas aeruginosa, Klebsiella pneumoniae, or Enterobacter species. Also for empiric treatment of febrile neutropenic patients and uncomplicated and complicated urinary tract infections (including pyelonephritis) caused by Escherichia coli or Klebsiella pneumoniae, when the infection is severe, or caused by Escherichia coli, Klebsiella pneumoniae, or Proteus mirabilis, when the infection is mild to moderate, including cases associated with concurrent bacteremia with these microorganisms. Also for the treatment of uncomplicated skin and skin structure infections caused by Staphylococcus aureus (methicillin-susceptible strains only) or Streptococcus pyogenes and complicated intra-abdominal infections (used in combination with metronidazole) caused by Escherichia coli, viridans group streptococci, Pseudomonas aeruginosa, Klebsiella pneumoniae, Enterobacter species, or Bacteroides fragilis.
• Pharmacology: Cefepime is a fourth-generation cephalosporin antibiotic developed in 1994. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both Gram-negative and Gram-positive organisms than third-generation agents. Cefepime has good activity against important pathogens including Pseudomonas aeruginosa, Staphylococcus aureus, and multiple drug resistant Streptococcus pneumoniae. A particular strength is its activity against Enterobacteriaceae. Whereas other cephalosporins are degraded by many plasmid- and chromosome-mediated beta-lactamases, cefepime is stable and is a front line agent when infection with Enterobacteriaceae is known or suspected
• Toxicity: Symptoms of overdose include seizures, encephalopathy, and neuromuscular excitability.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic. Cefepime is metabolized to N-methylpyrrolidine (NMP) which is rapidly converted to the N-oxide (NMP-N-oxide).
• Absorption: The absolute bioavailability of cefepime after an IM dose of 50 mg/kg was 82.3 (±15)% in eight patients.
• Half Life: 2.0 (± 0.3) hours in normal patients. The average half-life in patients requiring hemodialysis was 13.5 (± 2.7) hours and in patients requiring continuous peritoneal dialysis was 19.0 (± 2.0) hours.
• Protein Binding: The serum protein binding of cefepime is approximately 20% and is independent of its concentration in serum.
• Elimination: Elimination of cefepime is principally via renal excretion with an average (±SD) half-life of 2 (±0.3) hours and total body clearance of 120 (±8) mL/min in healthy volunteers. Cefepime is excreted in human milk.
• Distribution: * 18.0 ±2.0 L; * 0.3 ±0.1 L/kg [Pediatric]
• Clearance: * 120 mL/min [Healthy adult male receiving a single 30-minute IV infusions of cefepime]; * 3.3 +/-1.0 mL/min/kg [Petriatic patients (2 months – 11 years of age) receiving a single IV dose]
• References: Chapman TM, Perry CM: Cefepime: a review of its use in the management of hospitalized patients with pneumonia. Am J Respir Med. 2003;2(1):75-107. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Chapman TM, Perry CM: Cefepime: a review of its use in the management of hospitalized patients with pneumonia. Am J Respir Med. 2003;2(1):75-107. Pubmed