Cefuroxime

한글명:Cefuroxime

카스 번호55268-75-2

상품명:Cefuroxime

CBNumberCB7707485

분자식C16H16N4O8S

포뮬러 무게424.39

MOL 파일55268-75-2.mol

화학적 성질

녹는점	171.5-173°C
알파	D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer)
밀도	1.76
굴절률	1.6000 (estimate)
저장 조건	2-8°C
용해도	DMSO(약간 용해됨), 메탄올(약간 용해됨)
산도 계수 (pKa)	pKa 2.5(H2O) (Uncertain)
색상	흰색에서 황백색까지
수용성	145mg/L at 25℃
BCS Class	4
CAS 데이터베이스	55268-75-2(CAS DataBase Reference)
EPA	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)

위험 및 안전 성명

위험품 표기	Xn
위험 카페고리 넘버	42/43
안전지침서	22-24-37-45
WGK 독일	3
RTECS 번호	XI0329000

그림문자(GHS)

Cefuroxime 화학적 특성, 용도, 생산

개요
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.
화학적 성질
white crystalline solid
용도
Cefuroxime is a second-generation cephalosporin antibiotic.
주요 응용
Cefuroxime was synthesized by Glaxo Laboratories in 1975 as the first cephem antibiotic with the methoxyimino group at the 7 position. It is highly resistant to hydrolysis by cephalosporinase and is active against a variety of gram-negative bacteria, including indolepositive Proteus, Enterobacter, and Citrobacter. Cefuroxime is considered to be one of the socalled second-generation cephalosporins.
정의
ChEBI: A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain.
Antimicrobial activity
The methoximino side chain provides stability to most Gram-negative β-lactamases and it is active against most enterobacteria, including many multiresistant strains. Acinetobacter spp., S. marcescens and Ps. aeruginosa are resistant, although some Burkholderia cepacia strains are susceptible. Some anaerobic Gram-negative rods are susceptible, but B. fragilis is resistant. The minimum immobilizing concentration for the Nichol’s strain of T. pallidum is 0.01 mg/L.
Pharmacology
Cefuroxime acts bactericidally. It has a narrow spectrum of antimicrobial action. It is resistant to beta-lactamase action. It is highly active with respect to Gram-negative microorganisms (intestinal and hemophilial bacilli, salmonella, shigella, enterobacteria, and gonococci). It is also active with respect to Gram-positive microorganisms (staphylococci, streptococci). It is inactive with respect to various types of Pseudomonas, most strains of enterococci, many strains of Enterobacter cloacae, methylcillin-resistant staphylococci, and L. monocytogenes.
It is used for bacterial infections caused by microorganisms that are sensitive to the drug. These may be abdominal and gynecological infections, sepsis, meningitis, endocarditis, infections of the urinary and respiratory tracts, bones, joints, skin, and soft tissues. It is widely used for pneumonia as well as bacterial meningitis in children, and for post-operational infectious complications. Synonyms of this drug are ceftin, zinacef, curoxim, kefox, and many others.
Clinical Use
Cefuroxime axetil (Ceftin) is the 1-acetyoxyethyl ester ofcefuroxime. During absorption, this acid-stable, lipophilic,oral prodrug derivative of cefuroxime is hydrolyzed to cefuroximeby intestinal and/or plasma enzymes. The axetilester provides an oral bioavailability of 35% to 50% of cefuroxime,depending on conditions. Oral absorption of theester is increased by food but decreased by antacids and histamineH2-antagonists. The latter effect may be because ofspontaneous hydrolysis of the ester in the intestine becauseof the higher pH created by these drugs. Axetil is used forthe oral treatment of non–life-threatening infections causedby bacteria that are susceptible to cefuroxime. The prodrugform permits twice-a-day dosing for such infections.
부작용
It is well tolerated with little pain or phlebitis on injection. Minor hypersensitivity reactions and biochemical changes common to cephalosporins are described.
The axetil ester may cause diarrhea and, in some cases, vomiting. Changes in the bowel flora, sometimes with the appearance of C. difficile, have been reported in about 15% of patients. Vaginitis is reported in about 2% of female patients.

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