Ceftizoxime

Names

[ Name ]:
Ceftizoxime

[Synonym ]:
Ceftizoxima
SK&F 88373-Z
Ceftizoxime
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)-1-oxoethyl]amino]-8-oxo-, (6R,7R)-
Ceftizoxima [INN-Spanish]
(6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(methyloxy)imino]acetyl}amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Ceftix
(6R,7R)-7-[2-(2-Amino-4-thiazolyl)glyoxylamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid 72-(Z)-(O-Methyloxime)
Ceftizoximum
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Ceftizoximum [INN-Latin]
7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid
ceftizoximum [INN_la]
Cefizox
MFCD00072000
Eposerin
Epocelin
[6R-[6a,7b(Z)]]-7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

Biological Activity

[Description]:

Ceftizoxime is a bacterial inhibitor which acts by interfering with bacterial cell wall synthesis and inhibiting cross-linking of the peptidoglycan.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[Target]

bacterial[1]

[In Vitro]

Ceftizoxime is a new parenteral cephalosporin derivative which is more active against various gram-negative bacilli, including the opportunistic pathogens such as Enterobacter, Citrobacter species, and Serratia marcescens, than cephalosporins and cephamycins such as cefotiam, cefamandole, cefuroxime, cefotaxime, and cefmetazole. Ceftizoxime shows a broad spectrum of antibacterial activity against aerobic gram-positive and gram-negative bacteria[1].

[In Vivo]

The therapeutic effect of Ceftizoxime in mice infected with a small inoculum size is almost the same as that of cefotaxime[1]. Ceftizoxime is stable in biological fluids such as serum, urine, and tissue homogenates, but cefotaxime is unstable in rat tissue homogenates. Binding of ceftizoxime to serum protein in all species is the lowest of all the antibiotics: 31% for humans, 17% for dogs, and 32% for rats[2].

[Animal admin]

Rats[2] The animals used in this study include 6-week-old male JCL:ICR strain mice, 6-week-old male JCL:SD strain rats, 7.5- to 15.0-kg male beagle dogs, and 5.8- to 9.1-kg male rhesus monkeys. Ceftizoxime for injection is dissolved in 0.9% saline. Ceftizoxime is given in a dose of 20 mg/kg to all test animals. The volumes are: 0.25 mL per animal by the intravenous (i.v.) and subcutaneous routes to mice; 5 mL/kg of body weight by the intramuscular (i.m.) and i.v. routes to rats; and 0.5 mL/kg of body weight by the i.m. and i.v. routes to dogs and monkeys[1].

[References]

[1]. Kamimura T, et al. Ceftizoxime (Ceftizoxime), a new parenteral cephalosporin: in vitro and in vivo antibacterial activities. Antimicrob Agents Chemother. 1979 Nov;16(5):540-8.

[2]. Murakawa T, et al. Pharmacokinetics of ceftizoxime in animals after parenteral dosing. Antimicrob Agents Chemother. 1980 Feb;17(2):157-64.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Melting Point ]:
227 °C(dec.)

[ Molecular Formula ]:
C₁₃H₁₃N₅O₅S₂

[ Molecular Weight ]:
383.403

[ Exact Mass ]:
383.035797

[ PSA ]:
200.75000

[ LogP ]:
0.59

[ Index of Refraction ]:
1.849

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XI0367375

CHEMICAL NAME :: 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4- thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6-alpha,7-beta(Z)))-

CAS REGISTRY NUMBER :: 68401-81-0

LAST UPDATED :: 199712

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C13-H13-N5-O5-S2

MOLECULAR WEIGHT :: 383.43

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4563522

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4563522

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H317-H334

[ Precautionary Statements ]:
P261-P280-P284-P301 + P312 + P330-P304 + P340-P342 + P311

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S23-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2941905990

Customs

[ HS Code ]: 2941905990