Brand Name(s) in US
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Cefpodoxime proxetil

Brand Name(s) in US
Product Name
Cefpodoxime proxetil
CAS No.
87239-81-4
Chemical Name
Cefpodoxime proxetil
Synonyms
VANTIN;Cefodoxime Proxetil;BANAN;cefpodoxime axetil;CS-807;OTREON;ORELOX;JP,USP;R-3763;U-76253
CBNumber
CB5150483
Molecular Formula
C21H27N5O9S2
Formula Weight
557.6
MOL File
87239-81-4.mol
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Cefpodoxime proxetil Property

Melting point:
111-113°C
Density 
1.58±0.1 g/cm3(Predicted)
RTECS 
XI0367370
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
Soluble in DMSO
pka
8.13±0.60(Predicted)
form 
Solid
color 
White to Pale Yellow
Sensitive 
Light Sensitive
InChI
InChI=1S/C21H27N5O9S2/c1-9(2)33-21(30)35-10(3)34-19(29)15-11(6-31-4)7-36-18-14(17(28)26(15)18)24-16(27)13(25-32-5)12-8-37-20(22)23-12/h8-10,14,18H,6-7H2,1-5H3,(H2,22,23)(H,24,27)/b25-13-/t10?,14-,18-/m1/s1
InChIKey
LTINZAODLRIQIX-FBXRGJNPSA-N
SMILES
N12[C@@]([H])([C@H](NC(/C(/C3=CSC(N)=N3)=N\OC)=O)C1=O)SCC(COC)=C2C(OC(OC(OC(C)C)=O)C)=O
CAS DataBase Reference
87239-81-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38-42/43
Safety Statements 
22-26-36/37/39
WGK Germany 
3
HS Code 
30042000
Toxicity
LD50 in male, female mice, male, female rats (mg/kg): >10000, >10000, >2000, >2000 s.c., 3502, 2535, >4000, >4000 i.p.; >8000, >8000, >4000, >4000 orally (Nakao, 1988)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1098027
Product name
Cefpodoxime proxetil
Packaging
350mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
A3987
Product name
Cefpodoxime proxetil
Packaging
50mg
Price
$678
Updated
2023/01/07
Alfa Aesar
Product number
J66061
Product name
Cefpodoxime proxetil, 96%
Packaging
1g
Price
$285
Updated
2024/03/01
Cayman Chemical
Product number
25412
Product name
Cefpodoxime-d3
Purity
≥99% deuterated forms (d1-d3)
Packaging
500μg
Price
$136
Updated
2023/01/06
Cayman Chemical
Product number
25412
Product name
Cefpodoxime-d3
Purity
≥99% deuterated forms (d1-d3)
Packaging
1mg
Price
$245
Updated
2023/01/06
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Cefpodoxime proxetil Chemical Properties,Usage,Production

Brand Name(s) in US

Simplicef (veterinary drug)
Vantin (human drug)

Description

Cefpodoxime proxetil is an orally active, broad-spectrum cephalosporin especially useful in the treatment of bacterial infections in children. It is a prodrug converted by esterases in the GI walls to cefpodoxime, which reportedly has a bacteriostatic spectrum comparable to injectable third-generation cephem antibiotics.

Chemical Properties

Pale Yellow Solid

Originator

Sankyo (Japan)

Uses

A metabolite of Cefpodoxime Proxetil. An antibacterial.

Uses

An antibacterial. A broad spectrum, orally absorbed third generation cephalosporin, ester prodrug of the active free acid metabolite, Cefpodoxime

Uses

A broad spectrum antibiotic. Cefpodoxime proxetil is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against gram positive and gram negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Product is to be used for research and development only.

Definition

ChEBI: The 1-[(isopropoxycarbonyl)oxy]ethyl (proxetil) ester prodrug of cefpodoxime. After swallowing, hydrolysis of the ester group occurs in the intestinal epithelium, to release active cefpodoxime in the bloodstream. It is used to treat acute otitis media, pha yngitis, and sinusitis.

Manufacturing Process

A suspension of 30 g of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid in 300 ml acetone is mixed with 18.6 g 1,8-diazabicyclo[5.4.0]undec-7- ene. The solution obtained mixed at ca. 0°C with 261 g of a 14% toluene solution of 1-iodoethylisopropyl carbonate. After 4 hours the solution is poured onto a mixture of 600 ml of water and 21 ml conc. HCl. The pH of mixture is adjusted to ca. 1.0. The aqueous phase is extracted with 200 ml of hexane, mixed with 700 ml ethyl acetate and pH is adjusted to ca. 8.2. A solution of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid 1- (isopropoxycarbonyloxy)ethyl ester is obtained. Diastereoisomeric ratio B/(A+B)=0.49 (B is more apolar of the two diastereoisomers).
To a solution of 37.4 g of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid 1-(isopropoxycarbonyloxy)ethyl ester in 689 ml ethyl acetate at 2-3°C is added for 25 min 0.105 moles Z-(2-formamidothiazol-4-yl)-methoxy-acetyl chloride hydrochloride. After 25 min pH is adjusted to ca. 6.5-7.3. After 1 hour the organic layer is washed with water and concentrated. It was obtained a crude 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2- amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl ester, (6R,7R)- (Cefpodoxime proxetil). Diastereoisomeric ratio 0.49.
For purification 5 g of cefpodoxime proxetil are added to a mixture of 35 ml of methanol and 0.6 ml conc. H2SO4. The mixture is stirred for 90 min and slowly added during 25 min to a mixture of 2.1 g sodium bicarbonate and 400 ml water. The suspension obtained is stirred for 1 hour and the precipitate is isolated through a suction filter, washed with water and dried over phosphorus pentoxide at 35°C in a vacuum. 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2- carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)- 3-(methoxymethyl)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl ester, (6R,7R)-; (Cefpodoxime proxetil) is obtained in a diastereoisomeric ratio 0.528.

brand name

Vantin (Pharmacia & Upjohn);Banan.

Therapeutic Function

Antibiotic

Clinical Use

Cefpodoxime proxetil (Vantin) is the isopropyloxycarbonylethylester of the third-generation cephalosporincefpodoxime. This orally active prodrug derivative is hydrolyzedby esterases in the intestinal wall and in theplasma to provide cefpodoxime. Tablets and a powder forthe preparation of an aqueous suspension for oral pediatricadministration are available. The oral bioavailability of cefpodoximefrom the proxetil is estimated to be about 50%.Administration of the prodrug with food enhances its absorption.The plasma half-life is 2.2 hours, which permitsadministration on a twice-daily schedule.
Cefpodoxime is a broad-spectrum cephalosporin withuseful activity against a relatively wide range of Grampositiveand Gram-negative bacteria. It is also resistant tomany β-lactamases. Its spectrum of activity includes S.pneumoniae, Streptococcus pyogenes, S. aureus, H. influenzae,M. catarrhalis, and Neisseria spp. Cefpodoxime is alsoactive against members of the Enterobacteriaceae family,including E. coli, K. pneumoniae, and P. mirabilis. It thusfinds use in the treatment of upper and lower respiratory infections,such as pharyngitis, bronchitis, otitis media, andcommunity-acquired pneumonia. It is also useful for thetreatment of uncomplicated gonorrhea.

Side effects

Common side effects of Cefpodoxime proxetil include: headache, nausea, vomiting, diarrhoea, stomach pain, insomnia, vaginal swelling, redness, irritation, burning or itching. Severe may include: rash, itching, measles, difficulty breathing or swallowing, fever, sore throat, chills, or other signs of an infection coming back; swollen ankles or feet, dark urine, yellowing of the skin, easy bruising or bleeding, kidney problems. Seek medical attention if you have a serious adverse reaction.

Veterinary Drugs and Treatments

In dogs, cefpodoxime is indicated for the treatment of skin infections caused by Staphylococcus intermedius, Staphylococcus aureus, Streptococcus canis, E. coli, Proteus mirabilis, and Pasteurella multocida. Although not currently approved for cats, it may also be useful as well.

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Cefpodoxime proxetil Suppliers

Jiangxi ravel Biotechnology Co.,Ltd
Tel
400-880-2824 18107960669
Fax
18140514863
Email
79046690@qq.com
Country
China
ProdList
1267
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
XiaoGan ShenYuan ChemPharm co,ltd
Tel
15527768850
Email
1791901229@qq.com
Country
China
ProdList
8844
Advantage
52
Shandong Xiya Chemical Co., Ltd
Tel
4009903999 13355009207
Fax
0539-6365991
Email
3007715519@qq.com
Country
China
ProdList
18738
Advantage
57
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Hunan Hui Bai Shi Biotechnology Co., Ltd.
Tel
0731-85526065 13308475853
Email
ivy@hnhbsj.com
Country
China
ProdList
4552
Advantage
62
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View Lastest Price from Cefpodoxime proxetil manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cefpodoxime proxetil 87239-81-4
Price
US $0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
100kg/month
Release date
2021-10-28
Hebei Yanxi Chemical Co., Ltd.
Product
Cefpodoxime proxetil 87239-81-4
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100tons
Release date
2023-08-15
Hpets Biotech Company (Chongqing) Co.,ltd
Product
Cefpodoxime Proxetil 87239-81-4
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100 tons
Release date
2023-03-21

87239-81-4, Cefpodoxime proxetil Related Search:


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