80210-62-4 Usage
Chemical Properties
Off-White Solid
Uses
Different sources of media describe the Uses of 80210-62-4 differently. You can refer to the following data:
1. A metabolite of Cefpodoxime Proxetil. An antibacterial.
2. A metabolite of Cefpodoxime Proxetil (C243860). An antibacterial.
3. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 80210-62-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,0,2,1 and 0 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 80210-62:
(7*8)+(6*0)+(5*2)+(4*1)+(3*0)+(2*6)+(1*2)=84
84 % 10 = 4
So 80210-62-4 is a valid CAS Registry Number.
InChI:InChI=1/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1
80210-62-4Relevant articles and documents
Preparation method of cefpodoxime acid
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Paragraph 0028; 0030, (2021/07/31)
The invention discloses a preparation method of cefpodoxime acid. The method comprises the following steps: adding a proper amount of solvent, 7-amino-3-chloromethyl cephalosporanic acid as shown in a formula (III), sodium methoxide, a quaternary ammonium salt catalyst and potassium iodide into a reaction container, performing stirring reaction at 0-80 DEG C for 2-8 hours, then adding 2-(2-amino-4-thiazolyl)-2-(Z)-methoxy imino acetyl chloride as shown in a formula (IV), performing stirring reaction at 0-30 DEG C for 2-5 hours, and after the reaction is finished, performing post-treatment to obtain cefpodoxime acid as shown in a formula (II). The method is simple and easy to operate, high in reaction yield, green and environmentally friendly, avoids the use of inflammable and explosive raw materials with high toxicity, improves the purity of the product by the post-treatment process, and is suitable for industrial production.
A PROCESS FOR ALKYLATING THE HYDROXYMETHYL GROUP AT POSITION -3 OF CEPHALOSPORINS
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Page/Page column 9, (2017/09/27)
A process for alkylating the hydroxymethyl group at position -3 of 7-Amino-3- hydroxymethyl-3-cephem-4-carboxylic acid (D-7-ACA) using an alkylating agent, strong acid and a suitable solvent(s).
Preparation method of cefpodoxime proxetil
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Paragraph 0034; 0036; 0038; 0040, (2017/07/21)
The invention discloses a preparation method of cefpodoxime proxetil. In the method, a compound of formula II is used as an initial raw material, the intermediate compound of formula III is not separated during the process, and a crude product of cefpodoxime proxetil is synthesized by one step; and after that, a simple and easy recrystallization method is adopted for purifying the crude product of cefpodoxime proxetil to obtain cefpodoxime proxetil. In the preparation method disclosed by the invention, the yield is increased without reducing the quality, the obtained product has high purity, the synthesis path is simple, and the preparation method is suitable for industrial production.
