Cefodizime

Names

[ Name ]:
Cefodizime

[Synonym ]:
(6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(methyloxy)imino]acetyl}amino)-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]thio}methyl)-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}-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
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]-3-[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-, (6R,7R)-
Kenicef
MFCD00864926
7-{[(2-Amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]amino}-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-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-methoxyiminoacetyl]amino]-3-[[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
[6R-(6a,7b(Z))]-7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
CDZM
cefodizimum [INN_la]
S 77 1221 B
Modivid
(6R,7R)-7-[2-(2-Amino-4-thiazolyl)glyoxylamido]-3-[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid 72(Z)-(O-Methyloxime)
Neucef
Cefodizimum
Cefodizima
Cefodizme
Diezime
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-[[[5-(carboxymethyl)-4-methyl-2-thiazolyl]thio]methyl]-8-oxo-
Cefodizime

Biological Activity

[Description]:

Cefodizime is a third generation cephalosporin antibiotic with a broad spectrum of antibacterial activity. Cefodizime has no renal toxic effect, good tolerance and immune regulation activity, and is widely used in the treatment of severe infections of the respiratory and urinary tracts[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Bacterial[1]

[In Vitro]

Enterobacteriaceae including Escherichia coli, Klebsiella pneumoniae, Morganella morgan ii, Proteus mirabilis, Proteus vulgaris, Shigella sonnei, Yersinia enterocolitica and Salmonella species are all consistently sensitive to Cefodizime in vitro. Cefodizime has marginal but variable inhibitory activity against Citrobacter species including Citrobacter freundii, and Serratia marcescens. Cefodizime inhibits other Gram-negative bacteria including Haemophilus irifluenzae, Moraxella catarrhalis, Neisseria gonorrhoeae and Neisseria meningitidis[1]. Cefodizime is a bactericidal antibiotic having high affinity for penicillin-binding proteins lA/B, 2 and 3 of E. coli. The in vitro concentrations of Cefodizime resulting in bactericidal activity against susceptible strains of Gram-positive and Gram-negative bacteria are generally similar to the minimum inhibitory concentrations[1].

[In Vivo]

In experimentally-induced K. pneumoniae respiratory tract infections in mice, Cefodizime has activity comparable to Cefotaxime and Ceftazidime, and greater than that of Cefoperazone, Latamoxef, Cefuroxime or cefazolin for 8 hours after a single subcutaneous dose of 50 mg/kg. However, unlike these cephalosporins, Cefodizime continues to demonstrate pronounced bactericidal activity for at least 48 hours after a single injection. Complete bacterial clearance from the lung is achieved within 48 hours in 50% of the mice although Cefodizime is no longer detectable in the serum[1].

[References]

[1]. Barradell LB, et al. Cefodizime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use. Drugs. 1992 Nov;44(5):800-34.

[2]. Hu T, et al. Probing the interaction of cefodizime with human serum albumin using multi-spectroscopic and molecular docking techniques. J Pharm Biomed Anal. 2015 Mar 25;107:325-32.

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Molecular Formula ]:
C₂₀H₂₀N₆O₇S₄

[ Molecular Weight ]:
584.669

[ Exact Mass ]:
584.027649

[ PSA ]:
304.48000

[ LogP ]:
2.55

[ Index of Refraction ]:
1.852

[ Storage condition ]:
2-8°C

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S26-S36/37/39

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Related Compounds

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