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セフェピム

Cefepime

HCID 5479537
ノートを作成反応を作成見積依頼を出す印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
88040-23-7
標準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
分子式
C19H24N6O5S2
平均分子量
480.6 g/mol
単同位体質量
480.12496023

概要

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+).

名称と識別子

優先名称
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
現地名
セフェピム
英語名
Cefepime
分子式
C19H24N6O5S2
分子量
480.56

名称と別名

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
名称をさらに表示
セフピム(6R,7R)-7-[(Z)-2-(2-アミノ-4-チアゾリル)-2-メトキシイミノアセチルアミノ]-3-(1-メチルピロリジニオメチル)-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボキシラート(6R,6β)-7α-[[(2-アミノ-4-チアゾリル)[(Z)-メトキシイミノ]アセチル]アミノ]-8-オキソ-3-[[(1-メチルピロリジニウム)-1-イル]メチル]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸イオン(6R)-7α-[[(2-アミノ-4-チアゾリル)[(Z)-メトキシイミノ]アセチル]アミノ]-3-[(1-メチルピロリジニオ)メチル]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸イオンセフェピム1-{[(6R,7R)-7-[(2Z)-2-(2-アミノ-1,3-チアゾール-4-イル)-2-(メトキシイミノ)アセトアミド]-2-カルボキシラト-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-3-イル]メチル}-1-メチルピロリジン-1-イウム1-{[(6R,7R)-7-[(2Z)-2-(2-アミノ-1,3-チアゾール-4-イル)-2-(メトキシイミノ)アセトアミド]-2-カルボキシ-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-3-イル]メチル}-1-メチルピロリジン-1-イウム

物性

構造計算による物性

XLogP
-0.1
極性表面積
204 Ų
水素結合供与体数
2
水素結合受容体数
10
回転可能結合数
6
重原子数
32
形式電荷
0
複雑度
869

実験および物理化学的性質

Drugs · 3 件

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics

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

物理化学的性質

融点
150 C · 150 C
外見
Solid
色
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|
CAS データベース
88040 · 88040-23-7(CAS DataBase Reference)

化学的性質

化学的特性colorless Powder

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesSkin Sens. 1 (100%)

毒性情報

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 · 1 件

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 · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cefepime

DILI Positive

Intravenous

DOI:10.1016/j.drudis.2019.09.022

安全データ

化学と産業

薬理情報

ATC Code · 3 件

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 · 1 件

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 · 1 件

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 · 1 件

サプライヤー

読み込み中…

公開中の見積依頼

読み込み中…

関連反応

1 件
反応記録を作成
HRID 234109 の反応式
HRID 234109反応物としてuspto-grants-1997_01

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
(7R)-7-[(Z)-2-(2-アミノチアゾール-4-イル)-2-(メトキシイミノ)アセチルアミノ]-3-[(1-メチルピロリジニオ)メチル]セファム-3-エン-4-カルボン酸
1-メチル-1-[[(6R,7R)-2-カルボキシ-7-[[2-[(Z)-メトキシイミノ]-2-(2-アミノチアゾール-4-イル)アセチル]アミノ]-8-オキソ-5-チア-1-アザビシクロ[4.2.0]オクタン-2-エン]-3-イルメチル]ピロリジニウム
Cefepime sodium
Cefepime impurity
CEFEPIME ARGININE
Cefpim
FR 81335
Tsefepim
BMY 28142
Cefepime 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

データベース識別子

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_code
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 · 1 件

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 · 6 件

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 · 4 件

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

用途と製造

UsesUse (kg; approx.) in Germany (2009): >100
応用分野 · 3 件

用途セファロスポリン系抗菌作用

説明Cefepime 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.

使用Cefepime 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.

上流・下流製品情報

上流原料

塩化ナトリウム水和物ペンタンEthyl acetate solutionヨードメタンN,O-ビス(トリメチルシリル)アセトアミド五塩化りん炭酸カリウムDiphenyldiazomethane