| Identification | Back Directory | [Name]
Cefpodoxime | [CAS]
80210-62-4 | [Synonyms]
CPDX
Cefpodoxime
Cefpodoxima
Cefpodoximum
Unii-7R4F94tvgy
Cefpodoxime sulfate
Cefpodoximum [latin]
Cefpodoxima [spanish]
Cefpodoxime-D3Acid(98%,99Atom%D)
Cefpodoxime Proxetil EP Impurity A
(6R,7R)-7-{2-(2-Amino-4-thiazolyl)-2-[(Z)-methoxyimino]acetamido}-3-(methoxymethyl)-3-cephem-4-carboxylate
(7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetyl]amino]-3-methoxymethylcepham-3-ene-4-carboxylic acid
(6R,7R)-7α-[[(2-Aminothiazol-4-yl)[(Z)-methoxyimino]acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7α-[[(2-Amino-4-thiazolyl)[(Z)-methoxyimino]acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid
(6R-(6alpha,7beta(Z)))-7-(((2-Amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(methoxymethyl)-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-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-, (6R-(6alpha,7beta(Z)))- | [Molecular Formula]
C15H17N5O6S2 | [MDL Number]
MFCD00864906 | [MOL File]
80210-62-4.mol | [Molecular Weight]
427.46 |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
200-202°C | [density ]
1.78±0.1 g/cm3(Predicted) | [RTECS ]
XI0367365 | [storage temp. ]
-20°C Freezer | [solubility ]
Soluble in DMSO | [form ]
neat | [pka]
2.77±0.50(Predicted) | [Sensitive ]
Light Sensitive | [BRN ]
6021381 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
A metabolite of Cefpodoxime Proxetil (C243860). An antibacterial. | [Uses]
A metabolite of Cefpodoxime Proxetil. An antibacterial. | [Uses]
Cefpodoxime Proxetil metabolite antibiotic | [Definition]
ChEBI: A third-generation cephalosporin antibiotic with methoxymethyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamino substituents at positions 3 and 7, respectively, of the cephem skeleton. Given by mouth as its proxetil ester prodrug, it is used
to treat acute otitis media, pharyngitis, and sinusitis. | [Brand name]
Vantin (Pharmacia & Upjohn). | [Antimicrobial activity]
It
is stable to a wide range of plasmid-mediated β-lactamases.
It induces the chromosomal β-lactamases of Ps. aeruginosa,
Enterobacter spp., S. marcescens and Citrobacter spp., but is a
less potent inducer than cefoxitin. | [Biological Activity]
cefpodoxime, as known as r 3763, is a metabolite of cefpodoxime proxetil. it is demonstrated that cefpodoxime, as an oral third generation cephalosporin antibiotic, is active against most gram-positive and gram-negative bacteria.cefpodoxime suppresses bacterial septum and cell wall synthesis by binding to penicillin-binding proteins (pbps) located in the bacterial cytoplasmic membrane. | [Pharmacokinetics]
Oral absorption: c. 50%
Cmax 200 mg oral: 2.1 mg/L after 3 h
Plasma half-life: c. 2.2 h
Volume of distribution: c. 35 L
Plasma protein binding: 20–30%
Absorption and distribution
The ester is rapidly hydrolyzed to the parent compound in the small intestine. Bioavailability increases to 65% if taken with food, but antacids and H2-receptor antagonists reduce absorption. Unabsorbed drug is hydrolyzed and excreted in the feces.
It is well distributed and penetrates well into tissues (including lung tissue) and inflammatory exudate to achieve concentrations inhibitory to common pathogens.
Metabolism and excretion
The hydrolyzed prodrug is not subject to further metabolism. About 80% of the absorbed compound (30–40% of the original dose) appears in the urine over 24 h. Excretion is by glomerular filtration and tubular secretion; probenecid delays secretion and increases the peak plasma concentration.
Metabolism and excretion
The hydrolyzed prodrug is not subject to further metabolism. About 80% of the absorbed compound (30–40% of the original dose) appears in the urine over 24 h. Excretion is by glomerular filtration and tubular secretion; probenecid delays secretion and increases the peak plasma concentration.
| [Clinical Use]
Cefpodoxime has been used principally for the treatment of
upper and lower respiratory tract infections in children and
adults. | [Side effects]
The drug is well tolerated, but gastrointestinal disturbance
with diarrhea is common. Pseudomembranous colitis has
been reported occasionally. Other side effects are those common
to cephalosporins. | [in vitro]
cefpodoxime showed antibacterial activities against obligatory anaerobes and salmonella spp., shigella spp. and neisseria meningitides. the activity of cefpodoxime was less active than r95867, an active form of cs-834, against gram-negative bacteria [1]. cefpodoxime was quite stable to hydrolysis by β-lactamases produced from b. cereus and e. coli hb101/pbr322 [2]. | [in vivo]
male ddy mice were administered orally in a volume of 0.2 ml of 0.5% carboxymethyl cellulose sodium salt. after 7 days, it was shown that cefpodoxime had good efficacy against streptococcus spp. and k. pneumoniae infection in mice [1]. | [References]
[1]. sakagawa, e., otsuki, m., oh, t., & nishino, t. in-vitro and in-vivo antibacterial activities of cs-834, a new oral carbapenem. journal of antimicrobial chemotherapy, 1998; 42: 426-437.
[2]. fukuoka, t., ohya, s., utsui, y., domon, h., takenouchi, t., koga, t., … kuwahara, s. in vitro and in vivo antibacterial activities of cs-834, a novel oral carbapenem. antimicrobial agents and chemotherapy, 1997; 41(12): 2652–2663. |
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