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Cefzil (Molecule of the Month for June 2000)

cefprozil monohydrate

In addition to the structure shown above, there is a water molecule associated with the compound, leading to its IUPAC name being cefprozil monohydrate., or (6R,7S) 7[(R) - 2 amino-2(p hydroxyphenyl) acetamido]-8-oxo-3-propyl-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid monohydrate. Thus the empirical formula is more accurately represented as C18H19N3O5S.H2O Cefzil is one of the brand names of Cefproxil (the other is Procef). It is a broad spectrum non-addictive antbiotic which works by inhibiting the synthesis of bacterial cell walls. It is prescribed for skin infections and throat infections, and is usually taken in capsule form, or in suspension.

The powder cosists of a mixture of the cis and trans isomers, with >= 90 being in the trans form. . 14 250mg tablets cost $51.52, so it is relatively expensive. The recommended dosage is 500mg a day in one or two doses, which are more effectively absorbed if taken on an empty stomach. Effects are felt in one or two days, and the course lasts ten days. As it a cephalosporin, and thus related to penicillin, it is not recommended to take Cefzil if you have an allergic reaction to penicillin.

It is also not recommended if you are pregnant or over 60 years old, have impaired renal function, or are taking other antibiotics. There is a low incidence of side effects, but these include nausea, diahorrhea, and more rarely, vomiting, constipation, headaches and fever. If nausea is encounters, it is usually mild. There is no information on the overdose quantities, but it is not wise to exceed the dose recommended by your doctor. It is manufactured by Bristol Meyer Squibbs, mainly at their plant in East Syracuse. The other inactive ingredients in the capsules include cellulose, hydroxypropyl methyl cellulose, magnesium stearate, methyl cellulose, and sodium.

Formal Chemical Name (IUPAC)
(6R,7S) 7[(R) - 2 amino-2(p hydroxyphenyl) acetamido]-8-oxo-3-propyl-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid monohydrate

Picture of Cefzil 3D model

click on the picture of  Cefzil above to interact
with the 3D model of the
Cefzil structure
(this will open a new browser window)

Picture of Cefzil


Update by Karl Harrison
(Molecule of the Month for June 2000 )

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