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Cefuzonam

Cefuzonam structure

Cefuzonam 

structure
  • CAS No:

    82219-78-1

  • Formula:

    C16H15N7O5S4

  • Chemical Name:

    Cefuzonam

  • Synonyms:

    5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-,[6R-[6α,7β(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-,(6R,7R)-;1,2,3-Thiadiazole,5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid deriv.;(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;CL 251931;Cefuzoname;L 105;Cefuzonam;L 105 (cephem antibiotic);Antibiotic L-105;7β-[2-(2-Aminothiazol-4-yl-(Z)-2-(methoxyimino)acetamido]-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylic acid;CL 118523;112079-66-0

  • Categories:

    Active Pharmaceutical Ingredients  >  Antibiotics

Description

ChEBI: A second generation cephalosporin antibiotic.

Cefuzonam Basic Attributes

513.59

513.59

Characteristics

280.07000

1.36820

1.97 g/cm3

LD50 in female, male mice, female, male rats (mg/kg): 4117, >4800, 4281, 4222 i.v.; 6424, 6783, >8000, >8000 i.p.; all >10000 orally (Takita)

Safety Information

R36/37/38:Irritating to eyes, respiratory system and skin .

S26-S36

Xi

Cefuzonam Use and Manufacturing

Methods of Manufacturing

4.44g compound (I) (for its preparation see. Bucourt R, et a1. Tetrahedron, 1978, 34: 2233-2243) and 1.4lml of triethylamine dissolved in 70ml of dichloromethane, add 2.08g of pentachloride under ice cooling Phosphorus, stirring 15mine. The reaction solution was evaporated to dryness, and the residue was dissolved in 50ml of dichloromethane and. Concentrate again in 50ml of acetone mixture. The remainder was added to 50ml of acetone and filtered. After the filtrate was cooled, it was added to 2.53 g of compound (II) cooled in an ice bath (see Lewis GS, et al. J Med Chem, 1979, 22: 1214 for its preparation) in 50 ml of acetone and containing 0.84 g of sodium bicarbonate and 2.82 ml Triethylamine in 75ml water mixture. Stir for 0.5h under ice cooling, and then at room temperature for 1h. Acidify with 4mol/L hydrochloric acid to Ph=2, add 100ml water, and extract with ethyl acetate (3×150ml). The extracts were combined, washed twice with water, and dried with anhydrous magnesium sulfate. It was concentrated to obtain 5.7 g of compound (III). 4.4g of compound (III) was added to 30ml of 80% formic acid aqueous solution and stirred at room temperature for 2h. Filter, decolorize the filtrate with activated carbon, and filter again. The filtrate was concentrated to dryness at 40°C under reduced pressure, and the residue was impregnated with ether to obtain 2.4 g of white amorphous solid cefazolnam.

Uses

Used for septicemia, acute bronchitis, tonsillitis, trauma and secondary infections caused by surgical wounds, pharyngitis, arthritis, etc. caused by sensitive bacteria such as influenza bacillus, proteus genus, Escherichia coli, etc.

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