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Cefepime

HCID 5479537
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
88040-23-7
표준 SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]3(C)CCCC3)CS[C@H]12)c1csc(N)n1
InChIKey
HVFLCNVBZFFHBT-ZKDACBOMSA-N
분자식
C19H24N6O5S2
평균 분자량
480.6 g/mol
단동위원소 질량
480.12496023

개요

Cefepime is a cephalosporin bearing (1-methylpyrrolidinium-1-yl)methyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It has a role as an antibacterial drug. It is a cephalosporin and an oxime O-ether. It is a conjugate base of a cefepime(1+).

이름 및 식별자

우선 이름
Cefepime
IUPAC
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
영어명
Cefepime
분자식
C19H24N6O5S2
분자량
480.56

이름 및 동의어

cefepime88040-23-7CefepimaCefepimumCFPMBMY-28142Renapime(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylatecefepim807PW4VQE3VNRX-5022J01DE01
이름 더 보기
Cefepime sodiumCefepime impurityCEFEPIME ARGININECefpimFR 81335TsefepimBMY 28142Cefepime Jp
CHEBI:478164DTXSID70873208BMY28142(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(1-methylpyrrolidinium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylatePyrrolidinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-1-methyl-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-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(6R,7R)-7-(((2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl)amino)-3-((1-methylpyrrolidinium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate(6R,7R)-7-(((2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl)amino)-3-((1-methylpyrrolidin-1-ium-1-yl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

물성

구조 계산 물성

XLogP
-0.1
극성 표면적
204 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
10
회전 가능 결합 수
6
무거운 원자 수
32
형식 전하
0
복잡도
869

실험 및 물리화학적 성질

Drugs · 3건

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics

Solubility1.73e-02 g/L
Melting Point150ºC
Physical DescriptionSolid

물리화학적 성질

녹는점
150 C · 150 C
물리적 상태
Solid
색상
White to light yellow
InChIKey
HVFLCNVBZFFHBT-IZVURRFBNA-N
SMILES
N12C([C@@H](NC(=O)/C(=N\OC)/C3N=C(N)SC=3)[C@H]1SCC(C[N+]1(C)CCCC1)=C2C([O-])=O)=O |&1:2,16,r|

화학적 성질

colorless Powder

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Danger

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesSkin Sens. 1 (100%)

독성 정보

Adverse EffectsCefepime is usually well tolerated by both adult and pediatric patients. The most common adverse effects in adults are diarrhea and rash. The most common adverse effects in the pediatric population are fevers, diarrhea, and rash.
Toxicity Summary · 1건

In the event of a suspected overdose, the clinician should discontinue the drug or adjust the dose. Determining if the symptoms result from an actual cefepime overdose or preexisting comorbidities may be difficult. If suspicion is high or symptoms do not subside after dose adjusting or discontinuing, blood and cerebral spinal fluid levels should be obtained to evaluate if the toxicity stems from elevated cefepime levels. Cefepime-induced neurotoxicity (CIN) can lead to generalized periodic discharges and a triphasic wave pattern on EEG. Dialysis may be necessary in severe cases.

Drug Induced Liver Injury · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cefepime

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

안전 데이터

화학 및 산업

약리 정보

ATC Code · 3건

J01DE01

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingThe serum protein binding of cefepime is approximately 20%, independent of its concentration in serum.
Pharmacodynamics · 1건

Cefepime is a fourth-generation cephalosporin antibiotic. It is active against Gram-negative bacteria such as _Enterobacter_ spp., _Escherichia coli_, _Klebsiella pneumoniae_, _Proteus mirabilis_ and _Pseudomonas aeruginosa_, and Gram-positive bacteria such as _Staphylococcus aureus_ (methicillin-susceptible isolates only), _Streptococcus pneumoniae_, _Streptococcus pyogenes_ and Viridans group streptococci. Compared to third-generation cephalosporins, cefepime has an extended Gram-negative coverage. Whereas other cephalosporins are degraded by plasmid- and chromosome-mediated beta-lactamases, cefepime is stable and not significantly hydrolyzed by these enzymes. Cefepime is also a poor inducer of type 1 beta-lactamases and, therefore, a good alternative against bacteria resistant to third-generation cephalosporins. In animal models of infection, the time that the unbound plasma concentration of cefepime exceeds the minimum inhibitory concentration (MIC) of infecting organisms has been shown to correlate with treatment efficacy. It has been suggested that cefepime can cross the inflamed blood-brain barrier. This, along with its ability to inhibit γ-aminobutyric acid (GABA), could lead to the neurotoxic effects observed in some of the patients treated with cefepime.

Mechanism of Action · 1건

Cefepime is a bactericidal cephalosporin with a mode of action similar to other beta-lactam antibiotics. Cefepime disrupts bacterial cell walls by binding and inhibiting transpeptidases known as penicillin-binding proteins (PBPs), which are enzymes involved in the final stages of peptidoglycan layer synthesis. This results in the lysis and death of susceptible microorganisms. Cefepime has a broad spectrum of _in vitro_ activity that includes both Gram-positive and Gram-negative bacteria. Cefepime has affinity for PBP-3 and PBP-1 in _Escherichia coli_ and _Pseudomonas aeruginosa_, as well as PBP-2 in _E. coli_ and _Enterobacter cloacae_.

Biological Half-Life · 1건

관련 반응

1건
반응 기록 만들기
HRID 234109 반응식
HRID 234109반응물로uspto-grants-1997_01

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

데이터베이스 식별자

CAS
88040-23-7
PubChem CID
5479537
DTXSID
DTXSID70873208
ChEMBL
CHEMBL186
ChEBI
CHEBI:478164
UNII
807PW4VQE3
EC Number
643-019-5
Nikkaji
J39.157C
HS 번호
29419000
risk_code
36/37/38-42/43
hazard_code
Xi
safety_code
22-26-36/37/39

Healthy adult male volunteers (n=9) given cefepime had an average half-life of 2 hours. In patients requiring hemodialysis, the average half-life was 13.5 hours, and in patients requiring continuous peritoneal dialysis, the average half-life was 19 hours.

Metabolism/Metabolites · 1건

Less than 1% of cefepime is metabolized in the liver. Cefepime is metabolized to N-methylpyrrolidine (NMP), which then undergoes rapid oxidation to form NMP-N-oxide, a more stable compound. NMP-N-oxide is the predominant metabolite of cefepime, while NMP and the 7-epimer of cefepime are minor byproducts. It has been suggested that flavin-containing mixed-function oxygenase mediates the oxidation of NMP to NMP-N-oxide.

FDA Pharmacological Classification · 6건

807PW4VQE3

CEFEPIME

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Cefepime is a Cephalosporin Antibacterial.

CEFEPIME

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion · 4건

Healthy adult male volunteers (n=9) given a single intravenous infusion of 500 mg, 1 g, and 2 g of cefepime had a corresponding Cmax of 39.1, 81.7 and 163.9 μg/mL, and a corresponding AUC of 70.8, 148.5 and 284.8 h⋅μg/mL. On the other hand, healthy adult male volunteers given a single intramuscular infusion of 500 mg, 1 g, and 2 g of cefepime had a corresponding Cmax of 13.9, 29.6 and 57.5 μg/mL, a corresponding AUC of 60, 137 and 262 h⋅μg/mL, and a corresponding Tmax of 1.4, 1.6 and 1.5 h. A study in healthy adult male volunteers (n=7) that received clinically relevant doses for 9 days suggests that cefepime is not accumulated in the body. Between 250 mg and 2 g, cefepime follows a linear pharmacokinetic model, and the absolute bioavailability of cefepime in pediatric patients (n=8) given an intramuscular dose of 50 mg/kg was 82.3%.

Cefepime is mainly eliminated by the kidneys, and most of it is excreted unchanged. Approximately 85% of cefepime administered to normal subjects is excreted unchanged in urine. Less than 1% of the administered dose is recovered from urine as N-methylpyrrolidine (NMP), 6.8% as NMP-N-oxide, and 2.5% as an epimer. Dosage adjustments are required in patients with renal dysfunction or those undergoing hemodialysis, due to the importance of renal excretion in eliminating cefepime.

The average steady-state volume of distribution of cefepime is 18.0 L. In pediatric patients, the average steady-state volume of distribution is 0.3 L/kg.

Cefepime has a total body clearance of 120 mL/min in healthy volunteers, and in pediatric patients, the average total body clearance is 3.3 mL/min/kg. In geriatric patients (65 years of age and older) and patients with abnormal renal function, cefepime total body clearance decreases proportionally with creatinine clearance.

Cellular LocationsMembrane

용도 및 제조

UsesUse (kg; approx.) in Germany (2009): >100
응용 분야 · 2건

개요Cefepime is a new fourth-generation parenteral cephalosporine antibiotic launched in 1993 in Sweden and France. Cefepime has broad spectrum antimicrobial activity against Staphylococcus, Strepfococcus, Pseudomonas, and the Enterobacteriaceae, including many bacterial isolates that are resistant to commonly used ceftazidime and cefotaxime. Its efficacy has been demonstrated in the treatment of lower respiratory tract infections especially pneumonia, intra-abdominal and urinary tract infections, skin and soft tissue infections, chronic osteomyelitis and in prophylaxis of biliary tract and prostate infections. It is well tolerated by patients and is reported to exhibit no significant drug interactions.

용도Cefepime is used for bacterial infections caused by microorganisms that are sensitive to drugs in septicemia, bacteriemia, complicated infections of the upper and lower sections of the urinary system, pneumonia, pulmonary abscesses, emphysema of the pleura, fever in patients with neutropenia, and infected skin and soft tissue wounds. Synonyms of this drug are maxipime, cepim, cepimex, and others.

상·하류 제품 정보

상류 원료

염화나트륨물펜탄Ethyl acetate solution요오드 메탄N,O-비스(트리메틸시릴)아세트아마이드인 펜타염화물탄산 칼륨Diphenyldiazomethane

공급사100 곳

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