Cefuroxime

HCID 5479529CAS 55268-75-2

기본 정보

표준 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
분자식
C16H16N4O8S
평균 분자량
424.4 g/mol
단동위원소 질량
424.06888447

개요

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.

이름 및 식별자

우선 이름
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
영어명
Cefuroxime
분자식
C16H16N4O8S
분자량
424.39

이름 및 동의어

cefuroximeCephuroximeCefuroxim55268-75-2CefuroximoCefuroximumSharoxZinacef DanmarkCefuroximaCefuroxime AcidO1R9FJ93EDCHEBI:3515
이름 더 보기
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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
-0.2
극성 표면적
199 Ų
수소 결합 공여자 수
3
수소 결합 수용자 수
10
회전 가능 결합 수
8
무거운 원자 수
29

실험 및 물리화학적 성질

Drugs · 5건

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Metabolite of Cefuroxime axetil

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

LogP · 2건

-0.8

-0.17

Solubility · 2건

Freely soluble as sodium salt (145 mg/L)

2.84e-01 g/L

Human Drugs · 3건

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

FDA approved drugs -> Active ingredient

Watch group antibiotics

Melting Point · 2건

218-225 °C

218 - 225 °C

Physical DescriptionSolid

물리화학적 성질

녹는점
171.5 · 171.5-173°C
밀도
1.76 · 1.76
굴절률
1.6 · 1.6000 (estimate)
저장 조건
2 · 2-8°C
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa)
2.5 · pKa 2.5(H2O) (Uncertain)

화학적 성질

white crystalline solid

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Regulatory Information · 2건

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%)

독성 정보

Adverse Effects · 1건

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 · 5건

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

안전 데이터

wgk
3
rtecs
XI0329000
risk_code
42/43
hazard_code
Xn
safety_code
22-24-37-45
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 6건

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 · 1건

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 · 1건

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.

용도 및 제조

UsesUse (kg) in Switzerland (2009): >100
Use ClassificationVeterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
응용 분야 · 2건

개요Cefuroxime 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.

용도Cefuroxime is a second-generation cephalosporin antibiotic.

공급사50 곳

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]

추가 설명

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

관련 반응

20건

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