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Details

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
Structure of CEFEPIME, E-

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

HIDE SMILES / InChI

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MAXIPIME
Curative
MAXIPIME
Curative
MAXIPIME
Curative
MAXIPIME
Curative
MAXIPIME

Cmax

ValueDoseCo-administeredAnalytePopulation
29.6 μg/mL
1 g single, intramuscular
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
81.7 μg/mL
1 g single, intravenous
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
57.5 μg/mL
2 g single, intramuscular
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
163.9 μg/mL
2 g single, intravenous
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
13.9 μg/mL
500 mg single, intramuscular
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
39.1 μg/mL
500 mg single, intravenous
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
137 μg × h/mL
1 g single, intramuscular
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
148.5 μg × h/mL
1 g single, intravenous
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
262 μg × h/mL
2 g single, intramuscular
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
284.8 μg × h/mL
2 g single, intravenous
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
60 μg × h/mL
500 mg single, intramuscular
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens
70.8 μg × h/mL
500 mg single, intravenous
CEFEPIME HYDROCHLORIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
unknown, unknown
CEFEPIME HYDROCHLORIDE serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
unknown, unknown
CEFEPIME HYDROCHLORIDE serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Cefepime showed excellent activity against E. coli and K. pneumoniae, inhibiting 90% of these isolates at 0.12 mg/l. 84 isolates of methicillin-susceptible S. aureus were inhibited by 8 mg/l of cefepime.