Cefuroxime
- CAS No.
- 55268-75-2
- Chemical Name:
- Cefuroxime
- Synonyms
- CEFUROXIME AXETIL;Cefuroxime acid;cefuroxim;Cephuroxime;Cefuroxime VETRANAL;Cefuroxime Axetil EP Impurity D;-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;CXM;-7-((Z);Ketocef
- CBNumber:
- CB7707485
- Molecular Formula:
- C16H16N4O8S
- Molecular Weight:
- 424.39
- MOL File:
- 55268-75-2.mol
- Modify Date:
- 2024/7/2 8:55:17
| Melting point | 171.5-173°C |
|---|---|
| alpha | D20 +63.7° (c = 1.0 in 0.2M pH 7 phosphate buffer) |
| Density | 1.76 |
| refractive index | 1.6000 (estimate) |
| storage temp. | 2-8°C |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| pka | pKa 2.5(H2O) (Uncertain) |
| form | Solid |
| color | White to Off-White |
| Water Solubility | 145mg/L at 25℃ |
| BCS Class | 4 |
| CAS DataBase Reference | 55268-75-2(CAS DataBase Reference) |
| EPA Substance Registry System | 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)- (55268-75-2) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
|---|---|
| Signal word | Danger |
| Hazard statements | H334-H317 |
| Precautionary statements | P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501 |
| Hazard Codes | Xn |
| Risk Statements | 42/43 |
| Safety Statements | 22-24-37-45 |
| WGK Germany | 3 |
| RTECS | XI0329000 |
Cefuroxime Chemical Properties,Uses,Production
Description
Cefuroxime axetil is the acetoxyethyl ester and oral prodrug of cefuroxime, a second-generation cephalosporin. It has a broad spectrum of action and is resistant to most P-lactamases. Cefuroxime axed is indicated for serious bacterial infections, especially where no identification of organism(s) has been made.
Chemical Properties
white crystalline solid
Uses
Cefuroxime is a second-generation cephalosporin antibiotic.
Definition
ChEBI: A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain.
Application
Cefuroxime was synthesized by Glaxo Laboratories in 1975 as the first cephem antibiotic with the methoxyimino group at the 7 position. It is highly resistant to hydrolysis by cephalosporinase and is active against a variety of gram-negative bacteria, including indolepositive Proteus, Enterobacter, and Citrobacter. Cefuroxime is considered to be one of the socalled second-generation cephalosporins.
Antimicrobial activity
The methoximino side chain provides stability to most Gram-negative β-lactamases and it is active against most enterobacteria, including many multiresistant strains. Acinetobacter spp., S. marcescens and Ps. aeruginosa are resistant, although some Burkholderia cepacia strains are susceptible. Some anaerobic Gram-negative rods are susceptible, but B. fragilis is resistant. The minimum immobilizing concentration for the Nichol’s strain of T. pallidum is 0.01 mg/L.
Pharmacology
Cefuroxime acts bactericidally. It has a narrow spectrum of antimicrobial action. It is resistant to beta-lactamase action. It is highly active with respect to Gram-negative microorganisms (intestinal and hemophilial bacilli, salmonella, shigella, enterobacteria, and gonococci).
It is also active with respect to Gram-positive microorganisms (staphylococci, streptococci).
It is inactive with respect to various types of Pseudomonas, most strains of enterococci, many
strains of Enterobacter cloacae, methylcillin-resistant staphylococci, and L. monocytogenes.
It is used for bacterial infections caused by microorganisms that are sensitive to the drug.
These may be abdominal and gynecological infections, sepsis, meningitis, endocarditis, infections of the urinary and respiratory tracts, bones, joints, skin, and soft tissues. It is widely used
for pneumonia as well as bacterial meningitis in children, and for post-operational infectious
complications. Synonyms of this drug are ceftin, zinacef, curoxim, kefox, and many others.
Clinical Use
Cefuroxime axetil (Ceftin) is the 1-acetyoxyethyl ester ofcefuroxime. During absorption, this acid-stable, lipophilic,oral prodrug derivative of cefuroxime is hydrolyzed to cefuroximeby intestinal and/or plasma enzymes. The axetilester provides an oral bioavailability of 35% to 50% of cefuroxime,depending on conditions. Oral absorption of theester is increased by food but decreased by antacids and histamineH2-antagonists. The latter effect may be because ofspontaneous hydrolysis of the ester in the intestine becauseof the higher pH created by these drugs. Axetil is used forthe oral treatment of non–life-threatening infections causedby bacteria that are susceptible to cefuroxime. The prodrugform permits twice-a-day dosing for such infections.
Side effects
It is well tolerated with little pain or phlebitis on injection.
Minor hypersensitivity reactions and biochemical changes
common to cephalosporins are described.
The axetil ester may cause diarrhea and, in some cases,
vomiting. Changes in the bowel flora, sometimes with the
appearance of C. difficile, have been reported in about 15% of
patients. Vaginitis is reported in about 2% of female patients.
Cefuroxime Preparation Products And Raw materials
Raw materials
1of4
chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Frolic Pharmachem | +919711094561 | Himachal Pradesh, India | 94 | 58 | Inquiry |
| Sai Teja Drugs and Intermediates Pvt Ltd | +91-9963142345 +91-9963142345 | Telangana, India | 38 | 58 | Inquiry |
| Nectar Lifesciences Ltd | +91-9357244445 +91-9357244445 | Punjab, India | 29 | 58 | Inquiry |
| PROTECH TELELINKS | +91-8571891912 +91-9855060837 | Himachal Pradesh, India | 62 | 58 | Inquiry |
| OCEAN TRADING CORPORATION | +91(22) 24921669 | New Delhi, India | 6211 | 58 | Inquiry |
| Euroasia Trans Continental | +91 22 56349035-36 | New Delhi, India | 519 | 47 | Inquiry |
| Medilink Pharmachem | +91 (79) 3007-0133 | New Delhi, India | 424 | 50 | Inquiry |
| COVALENT LABORATORIES PRIVATE LTD | +91-40-49483333 | New Delhi, India | 7 | 58 | Inquiry |
| LUPIN LTD | +91 124 4885000 / +91 124 3325000 | New Delhi, India | 191 | 58 | Inquiry |
| AUROBINDO PHARMA LTD | +91 (40) 6672 1200 | New Delhi, India | 209 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| Frolic Pharmachem | 58 |
| Sai Teja Drugs and Intermediates Pvt Ltd | 58 |
| Nectar Lifesciences Ltd | 58 |
| PROTECH TELELINKS | 58 |
| OCEAN TRADING CORPORATION | 58 |
| Euroasia Trans Continental | 47 |
| Medilink Pharmachem | 50 |
| COVALENT LABORATORIES PRIVATE LTD | 58 |
| LUPIN LTD | 58 |
| AUROBINDO PHARMA LTD | 58 |
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