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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
Structure of CEFEPIME SULFATE

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

HIDE SMILES / InChI

Molecular Formula HO4S
Molecular Weight 97.071
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H25N6O5S2
Molecular Weight 481.569
Charge 1
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MAXIPIME

Approved Use

Cefepime 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 Date

1996
Curative
MAXIPIME

Approved Use

Cefepime 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 Date

1996
Curative
MAXIPIME

Approved Use

Cefepime 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 Date

1996
Curative
MAXIPIME

Approved Use

Cefepime 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 Date

1996
Curative
MAXIPIME

Approved Use

Cefepime 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 Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
unknown, unknown
CEFEPIME HYDROCHLORIDE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
unknown, unknown
CEFEPIME HYDROCHLORIDE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
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
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
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (0.8%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
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
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
PubMed

PubMed

TitleDatePubMed
Efficacy of cefepime in a Staphylococcus aureus endocarditis rat model.
1993 Nov
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
Retrospective review of neurotoxicity induced by cefepime and ceftazidime.
2003 Mar
Neurotoxicity induced by Cefepime in a very old hemodialysis patient.
2003 May
Fixed dose combination of cefepime plus amikacin prevent oxidative stress in liver of Mus musculus mice.
2008 Sep
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
Patents

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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:38:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:38:14 GMT 2023
Record UNII
YP33Y0FYAE
Record Status Validated (UNII)
Record Version
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Name Type Language
CEFEPIME SULFATE
Common Name English
PYRROLIDINIUM, 1-(((6R,7R)-7-(((2Z)-2-(2-AMINO-4-THIAZOLYL)-2-(METHOXYIMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-1-METHYL-, SULFATE (1:1)
Systematic Name English
CEFEPIME SULPHATE
Common Name English
Code System Code Type Description
PUBCHEM
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
PRIMARY
FDA UNII
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
PRIMARY
CAS
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
PRIMARY
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