セフロキシム

Cefuroxime

HCID 5479529CAS 55268-75-2

基本情報

標準SMILES
CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(COC(N)=O)CS[C@H]12)c1ccco1
InChIKey
JFPVXVDWJQMJEE-IZRZKJBUSA-N
分子式
C16H16N4O8S
平均分子量
424.4 g/mol
単同位体質量
424.06888447

概要

Cefuroxime is a 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain. It has a role as a drug allergen. It is a member of furans, a 3-(carbamoyloxymethyl)cephalosporin and an oxime O-ether.

名称と識別子

優先名称
Cefuroxime
IUPAC
(6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
現地名
セフロキシム
英語名
Cefuroxime
分子式
C16H16N4O8S
分子量
424.39

名称と別名

cefuroximeCephuroximeCefuroxim55268-75-2CefuroximoCefuroximumSharoxZinacef DanmarkCefuroximaCefuroxime AcidO1R9FJ93EDCHEBI:3515
名称をさらに表示
(6R,7R)-3-(カルバモイルオキシメチル)-7-[2-(2-フリル)-2-[(Z)-メトキシイミノ]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-2-カルボン酸7β-[[(Z)-2-(2-フリル)-2-(メトキシイミノ)-1-オキソエチル]アミノ]-3-[(カルバモイルオキシ)メチル]セファム-3-エン-4-カルボン酸セファロキシムセフロキシム(6R,7R)-7-[[2-フラニル[(Z)-メトキシイミノ]アセチル]アミノ]-3-[[(アミノカルボニル)オキシ]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(6R,7R)-3-[(カルバモイルオキシ)メチル]-7-[(2Z)-2-(フラン-2-イル)-2-(メトキシイミノ)アセトアミド]-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CEFUROXIME AXETILCefuroxime VETRANALCefuroxime Axetil EP Impurity D-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCXMKetocef-7-((Z)
(6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2-furanyl(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6alpha,7beta(Z)))-DTXSID5022774(6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-3-((carbamoyloxy)methyl)-7-(((2Z)-2-furan-2-yl-2-(methoxyimino)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-3-((carbamoyloxy)methyl)-7-((2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7R)-3-(carbamoyloxymethyl)-7-(((2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

データベース識別子

CAS
55268-75-2
PubChem CID
5479529
DTXSID
DTXSID5022774
ChEMBL
CHEMBL1436
ChEBI
CHEBI:3515
UNII
O1R9FJ93ED
EC Number
259-560-1
Nikkaji
J13.093A

物性

構造計算による物性

XLogP
-0.2
極性表面積
199 Ų
水素結合供与体数
3
水素結合受容体数
10
回転可能結合数
8
重原子数
29

実験および物理化学的性質

Drugs · 5 件

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Metabolite of Cefuroxime axetil

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

LogP · 2 件

-0.8

-0.17

Solubility · 2 件

Freely soluble as sodium salt (145 mg/L)

2.84e-01 g/L

Human Drugs · 3 件

Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins

FDA approved drugs -> Active ingredient

Watch group antibiotics

Melting Point · 2 件

218-225 °C

218 - 225 °C

Physical DescriptionSolid

物理化学的性質

融点
171.5 · 171.5-173°C
比旋光度
20 · D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer)
比重(密度)
1.76 · 1.76
屈折率
1.6 · 1.6000 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
DMSO(微量)、メタノール(微量)

化学的性質

化学的特性white crystalline solid

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H317 (31%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P319, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

Status: Active Update: 08-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21969

Cefuroxime: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6.alpha.,7.beta.(Z)]]-: Human health tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (31%)

毒性情報

Adverse Effects · 1 件

Similar to penicillins and most β-lactam antibiotics, cefuroxime is generally well-tolerated. However, cefuroxime may potentially lead to adverse drug reactions in some patients, as seen with other medications. The most commonly reported adverse drug reactions are gastrointestinal disturbances, including nausea, vomiting, and diarrhea. Additional gastrointestinal adverse drug reactions include anorexia, abdominal pain, dizziness, and headache. In cases of parenteral administration, local reactions at the injection site, including thrombophlebitis, can occur.

Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

cefuroxime

DILI Positive

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

wgk
3
rtecs
XI0329000
risk_code
42/43
hazard_code
Xn
safety_code
22-24-37-45
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 6 件

J - Antiinfectives for systemic use

S - Sensory organs

QJ - Antiinfectives for systemic use

QS - Sensory organs

QJ - Antiinfectives for systemic use

J01DC02

Protein Binding50% to serum protein
Pharmacodynamics · 1 件

Cefuroxime is a &beta;-lactam type antibiotic. More specifically, it is a second-generation cephalosporin. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal. Cefuroxime is effective against the following organisms: Aerobic Gram-positive Microorganisms: <i>Staphylococcus aureus</i>, <i>Streptococcus pneumoniae</i>, <i>Streptococcus pyogenes</i>. Aerobic Gram-negative Microorganisms: <i>Escherichia coli</i>, <i>Haemophilus influenzae</i> (including beta-lactamase-producing strains), <i>Haemophilus parainfluenzae</i>, <i>Klebsiella pneumoniae</i>, <i>Moraxella catarrhalis</i> (including beta-lactamase-producing strains), <i>Neisseria gonorrhoeae</i> (including beta-lactamase-producing strains). Spirochetes: <i>Borrelia burgdorferi</i>. Cefuroxime axetil is the prodrug

Mechanism of Action · 1 件

Cefuroxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefuroxime interferes with an autolysin inhibitor.

Biological Half-LifeApproximately 80 minutes following intramuscular or intravenous injection.
Metabolism/MetabolitesThe axetil moiety is metabolized to acetaldehyde and acetic acid.

用途と製造

UsesUse (kg) in Switzerland (2009): >100
Use ClassificationVeterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
応用分野 · 2 件

説明Cefuroxime axetil is the acetoxyethyl ester and oral prodrug of cefuroxime, a second-generation cephalosporin. It has a broad spectrum of action and is resistant to most P-lactamases. Cefuroxime axed is indicated for serious bacterial infections, especially where no identification of organism(s) has been made.

使用Cefuroxime is a second-generation cephalosporin antibiotic.

サプライヤー50 社

北京华美互利生物化工010-56205725 · [email protected]
天津始加生物医药科技有限公司15022261580 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]

補足説明

定義ChEBI: A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain.

関連反応

20 件

関連ノート

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