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HomeProduct name listCefpodoxime

Cefpodoxime

Synonym(s):(6R,7R)-7-{2-(2-Amino-4-thiazolyl)-2-[(Z)-methoxyimino]acetamido}-3-(methoxymethyl)-3-cephem-4-carboxylate;Cefpodoxime free acid

Cefpodoxime Structural

What is Cefpodoxime?

Absorption

Cefpodoxime proxetil is a prodrug that is absorbed from the gastrointestinal tract and de-esterified to its active metabolite, cefpodoxime. Following oral administration of 100 mg of cefpodoxime proxetil to fasting subjects, approximately 50% of the administered cefpodoxime dose was absorbed systemically.

Chemical properties

Off-White Solid

The Uses of Cefpodoxime

A metabolite of Cefpodoxime Proxetil. An antibacterial.

The Uses of Cefpodoxime

A metabolite of Cefpodoxime Proxetil (C243860). An antibacterial.

The Uses of Cefpodoxime

Cefpodoxime Proxetil metabolite antibiotic

Background

Cefpodoxime is an oral third generation cephalosporin antibiotic with effectiveness against most Gram positive and Gram negative bacteria. Commonly used to treat acute otitis media, pharyngitis, and sinusitis, cefpodoxime proxetil is a prodrug which is absorbed and de-esterified by the intestinal mucosa to Cefpodoxime.

What are the applications of Application

Cefpodoxime, Free Acid is a metabolite of Cefpodoxime Proxetil and an anti-bacterial

Indications

Indicated for the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms.

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

Cefpodoxime is shown to be effective against most Gram positive and Gram negative bacteria, except Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis.

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].

Metabolism

Not Available

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.

Properties of Cefpodoxime

Melting point: 200-202°C
Density  1.78±0.1 g/cm3(Predicted)
RTECS  XI0367365
storage temp.  Sealed in dry,Store in freezer, under -20°C
solubility  Soluble in DMSO
pka 2.77±0.50(Predicted)
form  neat
form  Solid
color  White to off-white
Sensitive  Light Sensitive
BRN  6021381
Stability: Hygroscopic

Safety information for Cefpodoxime

Signal word Danger
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H317:Sensitisation, Skin
H334:Sensitisation, respiratory
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P342+P311:IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

Computed Descriptors for Cefpodoxime

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