세파제돈나트륨염

세파제돈나트륨염
세파제돈나트륨염 구조식 이미지
카스 번호:
63521-15-3
한글명:
세파제돈나트륨염
동의어(한글):
세파제돈나트륨염
상품명:
Cefazedone sodium salt
동의어(영문):
Nsc304118;Refosporin sodium salt;Cefazedone, sodium salt;Cefazedone sodium salt USP/EP/BP;Sodium (6R,7R)-7-[[(3,5-dichloro-4-oxo-1(4H)-pyridyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;sodium (6R-trans)-7-[[(3,5-dichloro-4-oxo-1(4H)-pyridyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;(6R,7R)-7-[[2-(3,5-Dichloro-4-oxopyridin-1(4H)-yl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(3,5-dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-, monosodium salt, (6R-trans)-
CBNumber:
CB6878809
분자식:
C18H14Cl2N5NaO5S3
포뮬러 무게:
570.42503
MOL 파일:
63521-15-3.mol

세파제돈나트륨염 속성

안전

독성 LD50 in mice, rats, rabbits, dogs (mg/kg): 6800, 4225, 3200, 3000 i.v. (von Eberstein)

세파제돈나트륨염 C화학적 특성, 용도, 생산

Originator

Cefazedone Sodium,Arocor Holdings Inc.

Manufacturing Process

A solution of 1 eq. of the tert-butyl ester of 7-aminocephalosporanic acid and 1 eq. of dicyclohexylcarbodiimide in 100 ml of methylene chloride/DMF (1:1) is cooled to 0°C. The mixture is combined with 1 eq. of 3,5-dichloro-4- pyridone-1-acetic acid; after 5 min the ice bath is removed and the mixture agitated for another 30 min at 25°C. The thus-formed urea is filtered off and the filtrate filtered over silica gel (eluent: ethyl acetate/1% methanol). The solvent is concentrated by evaporation, and the thus-obtained tert-butyl ester of 7-(3,5-dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido)cephalosporanic acid is crystallized from ether.
1 eq. of the tert-butyl ester is dissolved in 30 ml of trifluoroacetic acid. After 30 minutes, the solution is evaporated and the thus-produced 7-(3,5-dichloro- 1,4-dihydro-4-oxo-1-pyridylacetamido)cephalosporanic acid crystallized from ether.
1 eq. of the obtained 7-(3,5-dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido) cephalosporanic acid is dissolved in 60 ml of saturated aqueous sodium bicarbonate solution at a pH of below 7 and combined with 1 eq. of 5-methyl- 1,3,4-thiadiazole-2-thiol in 20 ml of acetone. The reaction solution is agitated for 2 hours at 80°C and at a pH of 6.3 under a nitrogen atmosphere. The acetone is thereupon removed, the solution is washed with ether and acidified to pH 2. The thus-obtained 3-(1-methyltetrazolyl-5-mercaptomethyl)-7-(3,5- dichloro-1,4-dihydro-4-oxo-1-pyridylacetamido)-3-cephem-4-carboxylic acid is filtered off and dried. IR spectrum confirmed the structure of cefazedone.
In practice it is usually used as sodium salt.

Therapeutic Function

Antibiotic

세파제돈나트륨염 준비 용품 및 원자재

원자재

준비 용품


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