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HomeProduct name listCEFADROXIL

CEFADROXIL

  • CAS NO.:50370-12-2
  • Empirical Formula: C16H17N3O5S
  • Molecular Weight: 363.39
  • MDL number: MFCD00865091
  • EINECS: 256-555-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
CEFADROXIL Structural

What is CEFADROXIL?

Absorption

Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.

Toxicity

Nausea, vomiting, diarrhoea, allergic rashes may occur

Description

Cephadroxil is an orally administered antibiotic, which is very similar to cephalexin. After oral administration, its peak serum level is slightly lower than that of cephalexin, but it is excreted more slowly. Therefore, it can be used for oral administration at 8- or 12-hourly intervals (Buck and Price, 1977; Pfeffer et al., 1977). Cephadroxil is still available in a number of European countries (for example, Spain, Belgium, Luxembourg, Portugal, and Finland, among others).

Chemical properties

Cefadroxil is a light orange colored powder. It is a cephalosporin antibiotic and is used for the treatment of bacterial infections. Cefadroxil is stable under recommended storage conditions. Cefadroxil is not considered hazardous when handled under normal medical conditions and with good housekeeping

Originator

Oracefal,Bristol,France,1977

The Uses of CEFADROXIL

Antibacterial;Bacterial transpeptidase inhibitor

Background

Long-acting, broad-spectrum, water-soluble, cephalexin derivative.

Definition

ChEBI: A cephalosporin bearing methyl and (2R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.

Indications

For the treatment of the following infections (skin, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staphylococci and Streptococcus pyogenes

Manufacturing Process

1.8 g of sodium N-(1-methoxycarbonyl-1-propen-2-yl)-D(-)-α-amino-(4- hydroxyphenyl)acetate was suspended in 10 ml of acetone, and one droplet of N-methylmorpholine was added thereto, and the mixture was cooled to -15°C.There was added 0.85 g of ethyl chlorocarbonate thereto, and the mixture was reacted at -13°C to -10°C for 30 minutes, and then the reaction solution was cooled to -20°C.
On the other hand, 1 g of 7-amino-3-methyl-3-cephem-4-carboxylic acid was suspended in 20 ml of methanol, and 1.4 g of triethylamine was added thereto to be dissolved, and 0.4 ml of acetic acid was further added thereto. This solution was cooled to -20°C and the mixed acid anhydride prepared previously was added thereto. After the mixture was reacted at -20°C for 1 hour, the temperature of the reaction mixture was raised to 0°C over a period of 1 hour, and the mixture was reacted for 3 hours at the same temperature.
After the reaction, 1 ml of water was added to the reaction mixture, and the mixture was adjusted to a pH of 1.0 with concentrated hydrochloric acid while being cooled, and then stirred for 30 minutes, The insoluble matters were filtered off, and the filtrate was adjusted to a pH of 5.5 with triethylamine. This solution was concentrated under reduced pressure, and the residue was diluted with 20 ml of acetone to precipitate white crystals. The crystals were collected by filtration and washed with ethanol to obtain 1.46 g of white crystals of 7-[D(-)-α-amino-(4-hydroxyphenyl)acetamido]-3-methyl-3- cephem-4-carboxylic acid having a decomposition point of 197°C.

Therapeutic Function

Antibacterial

Health Hazard

Exposures to cefadroxil cause certain common side effects. These include nausea, vomiting, stomach disorders, rashes, itching, unusual tiredness or weakness, yellowing of the skin or eyes, red, swollen, or blistered skin, unusual bruising or bleeding, sore throat, respiratory distress, tightness in the chest, swelling of the mouth, face, lips, or tongue, decreased urination, dark urine, vaginal itching, odor, or discharge, fever, chills, joint pain, and seizures. Prolonged or long-term use of cefadroxil should be avoided.

Pharmacokinetics

Cefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.

Metabolism

Not Available

Precautions

Cefadroxil should be used only under proper medical health care since it has properties of penicillin allergy, renal function, gastrointestinal tract damage. Pregnant women and breast-feeding women should avoid exposure to cefadroxil.

Properties of CEFADROXIL

Melting point: 197°C (rough estimate)
Boiling point: 238°C (rough estimate)
Density  1.59
refractive index  1.6390 (estimate)
storage temp.  under inert gas (nitrogen or Argon) at 2–8 °C
solubility  Water:9.17(Max Conc. mg/mL);25.23(Max Conc. mM)
pka 3.12±0.50(Predicted)
form  powder or crystals
color  White to off-white
CAS DataBase Reference 50370-12-2

Safety information for CEFADROXIL

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
H334:Sensitisation, respiratory
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for CEFADROXIL

InChIKey BOEGTKLJZSQCCD-UEKVPHQBSA-N

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