Stereochemistry | ABSOLUTE |
Molecular Formula | C19H24N6O5S2 |
Molecular Weight | 480.561 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(C[N+]3(C)CCCC3)=C(N1C(=O)[C@H]2NC(=O)C(=N\OC)\C4=CSC(N)=N4)C([O-])=O
InChI
InChIKey=HVFLCNVBZFFHBT-FKULVZFESA-N
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
Cefepime is a fourth-generation cephalosporin antibiotic, which was developed in 1994. Cefepime has a broad spectrum in vitro activity that encompasses a wide range of Gram-positive and Gram-negative bacteria. Within bacterial cells, the molecular targets of cefepime are the penicillin binding proteins (PBP). It is FDA approved for the treatment of pneumonia, febrile neutropenia, uncomplicated UTI, uncomplicated skin infection and complicated intraabdominal infections. Common adverse reactions include rash, hypophosphatemia, diarrhea. Cefepime is metabolized to N-methylpyrrolidine (NMP) which is rapidly converted to the N-oxide (NMP-N-oxide). Urinary recovery of unchanged cefepime accounts for approximately 85% of the administered dose. Less than 1% of the administered dose is recovered from urine as NMP, 6.8% as NMP-N-oxide, and 2.5% as an epimer of cefepime. Because renal excretion is a significant pathway of elimination, patients with renal dysfunction and patients undergoing hemodialysis require dosage adjustment.
CNS Activity
Originator
Approval Year
Cmax
AUC
Doses
AEs
Sourcing
Sample Use Guides
Moderate to Severe Pneumonia: 1 to 2 g IV, every 8 to 12 hours; 10 days.
Empiric therapy for febrile neutropenic patients: 2 g IV, every 8 hours; 7 days.
Mild to Moderate Uncomplicated or Complicated Urinary Tract Infections, including pyelonephritis: 0.5 to 1 g IV/IM, every 12 hours; 7 to 10 days.
Severe Uncomplicated or Complicated Urinary Tract Infections, including pyelonephritis: 2 g IV, every 12 hours; 10 days.
Moderate to Severe Uncomplicated Skin and Skin Structure Infections: 2 g IV, every 12 hours; 10 days.
Complicated Intra-abdominal Infections (used in combination with metronidazole): 2 g IV, every 8-12 hours; 7 to 10 days.
Route of Administration:
Other
SUBSTANCE RECORD