CEFADROXIL Chemical Properties

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

InChIKey

BOEGTKLJZSQCCD-UEKVPHQBSA-N

CAS DataBase Reference

50370-12-2

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-42/43

Safety Statements 

26-36

WGK Germany 

2

RTECS 

XI0337000

MSDS

• Language:English Provider:SigmaAldrich

CEFADROXIL Usage And Synthesis

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

Uses

Antibacterial;Bacterial transpeptidase inhibitor

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.

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.

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.

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