Cefuzonam

Title: Cefuzonam
CAS Registry Number: 82219-78-1
CAS Name: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(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
Additional Names: (-)-(6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72-(Z)-(O-methyloxime); 7b-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[(1,2,3-thiadiazol-5-yl)thiomethyl]ceph-3-em-4-carboxylic acid
Manufacturers' Codes: CL-118523
Molecular Formula: C16H15N7O5S4
Molecular Weight: 513.59
Percent Composition: C 37.42%, H 2.94%, N 19.09%, O 15.58%, S 24.97%
Literature References: Semi-synthetic third generation cephalosporin. Prepn and bactericidal activity: W. V. Curran, A. S. Ross, FR 2488258; eidem, US 4399132 (1982, 1983 both to Am. Cyanamid); eidem, J. Antibiot. 36, 179 (1983). Improved prepn of sodium salt: K. Naito et al., EP 145395 (1985 to Takeda). In vitro antibacterial spectrum: M. Hikada et al., J. Antimicrob. Chemother. 18, 585 (1986). Toxicity study: S. Takita, Chemotherapy (Tokyo) 34, Suppl. 3, 96 (1986). Conference proceedings: Recent Adv. Chemother., Antimicrobial Sect. 2., Proc. 14th Int. Congr. Chemother., Kyoto 1985, J. Ishigami, Ed. (Univ. Tokyo Press, Tokyo, 1985) pp 887-908. Series of articles: Chemotherapy (Tokyo) 34, Suppl. 3, 1-732 (1986).
Properties: White amorphous solid. 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).
Toxicity data: 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)
Derivative Type: Sodium salt dihydrate
Manufacturers' Codes: L-105 (Lederle); CL-251931; LJC-10305
Trademarks: Cosmosin (Nippon Lederle)
Molecular Formula: C16H14N7NaO5S4.2H2O
Molecular Weight: 571.61
Percent Composition: C 33.62%, H 3.17%, N 17.15%, Na 4.02%, O 19.59%, S 22.44%
Properties: Yellowish crystalline powder. Sol in water.
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
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Cefuzonam
Cefuzonam.png
Systematic (IUPAC) name
(6R,7R)-7-([(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino)-8-oxo-3-(thiadiazol-5-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Legal status Prescription only
Identifiers
CAS number 82219-78-1 YesY
ATC code None
PubChem CID 6336505
ChemSpider 4891670 N
UNII 860MT00T7T YesY
KEGG D03432 YesY
Chemical data
Formula C16H15N7O5S4 
Mol. mass 513.59 g/mol
 N (what is this?)  (verify)

Cefuzonam (INN) is a second-generation cephalosporin antibiotic.