Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H24N6O5S2.H2O4S |
| Molecular Weight | 578.64 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.[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=JCRAHWHSZYCYEI-LSGRDSQZSA-N
InChI=1S/C19H24N6O5S2.H2O4S/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;1-5(2,3)4/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29);(H2,1,2,3,4)/b23-12-;/t13-,17-;/m1./s1
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.rxlist.com/maxipime-drug.htm
https://www.drugs.com/cdi/cefepime.html
Curator's Comment: description was created based on several sources, including:
http://www.rxlist.com/maxipime-drug.htm
https://www.drugs.com/cdi/cefepime.html
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
Curator's Comment: It has been confirmed that the concentration of cefepime in cerebrospinal fluid (CSF) could reach the 10% of its concentration in plasma, exceeding the inhibitory concentration to 90% of organisms (MIC(90)) for common bacteria. However, the blood-brain barrier (BBB) penetration ability of cefepime is still unclear
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2354204 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | MAXIPIME Approved UseCefepime for injection, USP is indicated in the treatment of the following infections caused by susceptible strains of the designated microorganisms (see also PRECAUTIONS: Pediatric Use and DOSAGE AND ADMINISTRATION ): Pneumonia (moderate to severe) caused by Streptococcus pneumoniae, including cases associated with concurrent bacteremia, Pseudomonas aeruginosa, Klebsiella pneumoniae , or Enterobacter species. Empiric Therapy for Febrile Neutropenic Patients. Cefepime as monotherapy is indicated for empiric treatment of febrile neutropenic patients. In patients at high risk for severe infection (including patients with a history of recent bone marrow transplantation, with hypotension at presentation, with an underlying hematologic malignancy, or with severe or prolonged neutropenia), antimicrobial monotherapy may not be appropriate. Insufficient data exist to support the efficacy of cefepime monotherapy in such patients. (See CLINICAL STUDIES .) 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. Uncomplicated Skin and Skin Structure Infections caused by Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. 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. (See CLINICAL STUDIES .) To reduce the development of drug-resistant bacteria and maintain the effectiveness of cefepime for injection, USP and other antibacterial drugs, cefepime for injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date1996 |
|||
| Curative | MAXIPIME Approved UseCefepime for injection, USP is indicated in the treatment of the following infections caused by susceptible strains of the designated microorganisms (see also PRECAUTIONS: Pediatric Use and DOSAGE AND ADMINISTRATION ): Pneumonia (moderate to severe) caused by Streptococcus pneumoniae, including cases associated with concurrent bacteremia, Pseudomonas aeruginosa, Klebsiella pneumoniae , or Enterobacter species. Empiric Therapy for Febrile Neutropenic Patients. Cefepime as monotherapy is indicated for empiric treatment of febrile neutropenic patients. In patients at high risk for severe infection (including patients with a history of recent bone marrow transplantation, with hypotension at presentation, with an underlying hematologic malignancy, or with severe or prolonged neutropenia), antimicrobial monotherapy may not be appropriate. Insufficient data exist to support the efficacy of cefepime monotherapy in such patients. (See CLINICAL STUDIES .) 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. Uncomplicated Skin and Skin Structure Infections caused by Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. 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. (See CLINICAL STUDIES .) To reduce the development of drug-resistant bacteria and maintain the effectiveness of cefepime for injection, USP and other antibacterial drugs, cefepime for injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date1996 |
|||
| Curative | MAXIPIME Approved UseCefepime for injection, USP is indicated in the treatment of the following infections caused by susceptible strains of the designated microorganisms (see also PRECAUTIONS: Pediatric Use and DOSAGE AND ADMINISTRATION ): Pneumonia (moderate to severe) caused by Streptococcus pneumoniae, including cases associated with concurrent bacteremia, Pseudomonas aeruginosa, Klebsiella pneumoniae , or Enterobacter species. Empiric Therapy for Febrile Neutropenic Patients. Cefepime as monotherapy is indicated for empiric treatment of febrile neutropenic patients. In patients at high risk for severe infection (including patients with a history of recent bone marrow transplantation, with hypotension at presentation, with an underlying hematologic malignancy, or with severe or prolonged neutropenia), antimicrobial monotherapy may not be appropriate. Insufficient data exist to support the efficacy of cefepime monotherapy in such patients. (See CLINICAL STUDIES .) 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. Uncomplicated Skin and Skin Structure Infections caused by Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. 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. (See CLINICAL STUDIES .) To reduce the development of drug-resistant bacteria and maintain the effectiveness of cefepime for injection, USP and other antibacterial drugs, cefepime for injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date1996 |
|||
| Curative | MAXIPIME Approved UseCefepime for injection, USP is indicated in the treatment of the following infections caused by susceptible strains of the designated microorganisms (see also PRECAUTIONS: Pediatric Use and DOSAGE AND ADMINISTRATION ): Pneumonia (moderate to severe) caused by Streptococcus pneumoniae, including cases associated with concurrent bacteremia, Pseudomonas aeruginosa, Klebsiella pneumoniae , or Enterobacter species. Empiric Therapy for Febrile Neutropenic Patients. Cefepime as monotherapy is indicated for empiric treatment of febrile neutropenic patients. In patients at high risk for severe infection (including patients with a history of recent bone marrow transplantation, with hypotension at presentation, with an underlying hematologic malignancy, or with severe or prolonged neutropenia), antimicrobial monotherapy may not be appropriate. Insufficient data exist to support the efficacy of cefepime monotherapy in such patients. (See CLINICAL STUDIES .) 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. Uncomplicated Skin and Skin Structure Infections caused by Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. 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. (See CLINICAL STUDIES .) To reduce the development of drug-resistant bacteria and maintain the effectiveness of cefepime for injection, USP and other antibacterial drugs, cefepime for injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date1996 |
|||
| Curative | MAXIPIME Approved UseCefepime for injection, USP is indicated in the treatment of the following infections caused by susceptible strains of the designated microorganisms (see also PRECAUTIONS: Pediatric Use and DOSAGE AND ADMINISTRATION ): Pneumonia (moderate to severe) caused by Streptococcus pneumoniae, including cases associated with concurrent bacteremia, Pseudomonas aeruginosa, Klebsiella pneumoniae , or Enterobacter species. Empiric Therapy for Febrile Neutropenic Patients. Cefepime as monotherapy is indicated for empiric treatment of febrile neutropenic patients. In patients at high risk for severe infection (including patients with a history of recent bone marrow transplantation, with hypotension at presentation, with an underlying hematologic malignancy, or with severe or prolonged neutropenia), antimicrobial monotherapy may not be appropriate. Insufficient data exist to support the efficacy of cefepime monotherapy in such patients. (See CLINICAL STUDIES .) 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. Uncomplicated Skin and Skin Structure Infections caused by Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes. 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. (See CLINICAL STUDIES .) To reduce the development of drug-resistant bacteria and maintain the effectiveness of cefepime for injection, USP and other antibacterial drugs, cefepime for injection, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date1996 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
29.6 μg/mL |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
81.7 μg/mL |
1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
57.5 μg/mL |
2 g single, intramuscular dose: 2 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
163.9 μg/mL |
2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
13.9 μg/mL |
500 mg single, intramuscular dose: 500 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
39.1 μg/mL |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
137 μg × h/mL |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
148.5 μg × h/mL |
1 g single, intravenous dose: 1 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
262 μg × h/mL |
2 g single, intramuscular dose: 2 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
284.8 μg × h/mL |
2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
60 μg × h/mL |
500 mg single, intramuscular dose: 500 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
70.8 μg × h/mL |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
CEFEPIME HYDROCHLORIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2 h |
unknown, unknown |
CEFEPIME HYDROCHLORIDE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
80% |
unknown, unknown |
CEFEPIME HYDROCHLORIDE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
2 g 3 times / day multiple, intravenous Highest studied dose|Recommended Dose: 2 g, 3 times / day Route: intravenous Route: multiple Dose: 2 g, 3 times / day Sources: |
unhealthy, 53.2 years n = 10 Health Status: unhealthy Condition: Renal Replacement Therapy Age Group: 53.2 years Sex: M+F Population Size: 10 Sources: |
|
1 g 2 times / day multiple, intravenous|intramuscular Dose: 1 g, 2 times / day Route: intravenous|intramuscular Route: multiple Dose: 1 g, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (1.1%) Sources: |
2 g 2 times / day multiple, intravenous|intramuscular Dose: 2 g, 2 times / day Route: intravenous|intramuscular Route: multiple Dose: 2 g, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (2%) Sources: |
500 mg 2 times / day multiple, intravenous|intramuscular Dose: 500 mg, 2 times / day Route: intravenous|intramuscular Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (0.8%) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Rash | 1.1% Disc. AE |
1 g 2 times / day multiple, intravenous|intramuscular Dose: 1 g, 2 times / day Route: intravenous|intramuscular Route: multiple Dose: 1 g, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Rash | 2% Disc. AE |
2 g 2 times / day multiple, intravenous|intramuscular Dose: 2 g, 2 times / day Route: intravenous|intramuscular Route: multiple Dose: 2 g, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Rash | 0.8% Disc. AE |
500 mg 2 times / day multiple, intravenous|intramuscular Dose: 500 mg, 2 times / day Route: intravenous|intramuscular Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Efficacy of cefepime in a Staphylococcus aureus endocarditis rat model. | 1993 Nov |
|
| Nonconvulsive status epilepticus associated with cephalosporins in patients with renal failure. | 2001 Aug |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
| Metronidazole-induced encephalopathy in a uremic patient: a case report. | 2001 Sep |
|
| Reversible metronidazole-induced lesions of the cerebellar dentate nuclei. | 2002 Jan 3 |
|
| Retrospective review of neurotoxicity induced by cefepime and ceftazidime. | 2003 Mar |
|
| Neurotoxicity induced by Cefepime in a very old hemodialysis patient. | 2003 May |
|
| Cefepime- and cefixime-induced encephalopathy in a patient with normal renal function. | 2005 Dec 13 |
|
| Invasive fungal infection of the maxilla following dental extractions in a patient with chronic obstructive pulmonary disease. | 2006 Mar |
|
| Encephalopathy with myoclonic jerks resulting from ceftazidime therapy: an under-recognized potential side-effect when treating febrile neutropenia. | 2007 Feb |
|
| Fixed dose combination of cefepime plus amikacin prevent oxidative stress in liver of Mus musculus mice. | 2008 Sep |
|
| Probable trimethoprim/sulfamethoxazole-induced higher-level gait disorder and nocturnal delirium in an elderly man. | 2009 Jan |
|
| Cefepime-related encephalopathy in peritoneal dialysis patients. | 2011 Feb |
|
| Investigation of the effects of some drugs and phenolic compounds on human dihydrofolate reductase activity. | 2015 Mar |
|
| Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
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
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13239647
Created by
admin on Fri Dec 15 15:38:14 GMT 2023 , Edited by admin on Fri Dec 15 15:38:14 GMT 2023
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YP33Y0FYAE
Created by
admin on Fri Dec 15 15:38:14 GMT 2023 , Edited by admin on Fri Dec 15 15:38:14 GMT 2023
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107648-78-2
Created by
admin on Fri Dec 15 15:38:14 GMT 2023 , Edited by admin on Fri Dec 15 15:38:14 GMT 2023
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PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
