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Cefuroxime

HCID 5479529
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
55268-75-2
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
424.06888465

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

cefuroxime55268-75-2CephuroximeCefuroximoCefuroximumCefuroximZinacef DanmarkSharoxCefuroximaCefuroxime 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 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 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-[(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

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
형식 전하
0
복잡도
798

실험 및 물리화학적 성질

Drugs · 5건

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Metabolite of Cefuroxime axetil

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)

안전 및 규제

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

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

REACH registered substance: Cefuroxime (EC: 259-560-1)

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.

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.
FDA Pharmacological Classification · 6건

O1R9FJ93ED

CEFUROXIME

관련 반응

20건
반응 기록 만들기
HRID 377529 반응식
HRID 377529반응물로uspto-grants-2000_02
HRID 543529 반응식
HRID 543529반응물로uspto-grants-1984_05
HRID 543530 반응식
HRID 543530반응물로uspto-grants-1984_05
HRID 745968 반응식
HRID 745968반응물로uspto-grants-1986_07
HRID 745969 반응식
HRID 745969반응물로uspto-grants-1986_07
HRID 894826 반응식
HRID 894826생성물로uspto-grants-1981_08
HRID 894832 반응식
HRID 894832생성물로uspto-grants-1981_08
HRID 894833 반응식
HRID 894833생성물로uspto-grants-1981_08
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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
산도 계수 (pKa)
2.5 · pKa 2.5(H2O) (Uncertain)
물리적 상태
Solid
색상
흰색에서 황백색까지
수용성
145 mg/L · 145mg/L at 25℃
BCS Class
4 · 4
주요 응용
임상 시험
InChIKey
JFPVXVDWJQMJEE-IZRZKJBUSA-N
SMILES
N12[C@@]([H])([C@H](NC(/C(/C3=CC=CO3)=N\OC)=O)C1=O)SCC(COC(N)=O)=C2C(O)=O
EPA
5 · 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)- (55268-75-2)

화학적 성질

white crystalline solid

Toxicity Summary
Signs 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
EPA Human Health Benchmarks for Pharmaceuticals · 6건

Cefuroxime

11.7

49.3

For pharyngitis/tonsillitis (mild to moderate), dosage is 250 mg every 12 hours.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 500 mg/day, Lowest Therapeutic Dose (LTD): 6.3 mg/kg-day, and Screening Dose: 0.002 mg/kg-day.

21-Oct-21

안전 데이터

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

Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial

Chemical Structure [CS] - Cephalosporins

Cefuroxime is a Cephalosporin Antibacterial.

CEFUROXIME

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionAbsorbed from the gastrointestinal tract. Absorption is greater when taken after food (absolute bioavailability increases from 37% to 52%).
Cellular LocationsCytoplasm

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.

상·하류 제품 정보

상류 원료

Trichloroacetyl isocyanate케프록심 나트륨4-carboxylic acid소듐 2-에틸헥사노에이트트리에틸아민Methoxyiminoacetic acid인 펜타염화물Cephalothin sodium아족시메탄푸란염산(Z)-2-메톡시이미노-2-(푸릴-2-일)아세트산암모늄염인산이소시아나타이드이염화물데스에틸아세테이트(E)-CefuroxiMeAxetil[6R-[6alpha,7beta(Z)]]-7-[2-furyl(methoxyimino)acetamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidcefuracetime7-아미노세팔로스포란산

하류 제품

Cefuroxime 1-acetoxyethyl ester이소프로필에테르

추가 설명

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