Composition of the antibiotic 'amoxicillin'?

[green_dragon_1]

Hi,
Can anyone tell me what the chemical composition of amoxicillin is? i.e. is it based on penicillin? If not then what IS it based on?

Cheers,
dragon

[Smeghead]

It’s based on penicillin, with some structural modifications. A quick google search will get you the exact structure.

[Duck_Duck_Goose]

[takes deep breath]

RxList Page Not Found

Amoxicillin is a semisynthetic antibiotic, an analog of ampicillin, with a broad spectrum of bactericidal activity against many gram-positive and gram-negative microorganisms.

Chemically it is (2S,5R,6R)-6-[(R)-(-)-2-amino-2-(p-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate.

The amoxicillin molecular formula is C16H19N3O5S·3H2O, and the molecular weight is 419.45.

RxList Page Not Found

Penicillin V potassium is the potassium salt of penicillin V. This chemically improved form combines acid stability with immediate solubility and rapid absorption. It is designated 4-thia-1-azabicyclo[3.2.0]-heptane-2-carboxylic acid, 3,3 -dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-, monopotassium salt, [2S-(2a,5a,6b)]-. The empirical formula is C16H17KN2O5S, and the molecular weight is 388.48.

[whew]

I have no idea what I just said. It makes sense to you, GD?

[Qadgop_the_Mercotan]

Thanks for the hard data, DDG.

Amoxicillin, is an aminopenicillin. Penicillin is a naturally occurring antibiotic, produced by a species of fungus. To get Amoxicillin, penicillin is taken, and then treated biochemically to alter its structure, giving it certain advantages over penicillin (specifically a broader spectrum, or ability to kill a wider variety of bacteria, especially many gram-negative bacteria). It is therefore known as a semi-synthetic penicillin, taking the native molecule and altering it.

There are also synthetic penicillins made completely in the lab, not using naturally occuring penicillin as a starting block, but they are rather costly to make. And since they show no advantages over the semi-synthetic ones, they are not in use.

Aminopenicillins are semisynthetic derivative of 6-APA which have a free amino group at the a-position at R on the penicillin nucleus. Partly because of this polar group, aminopenicillins have enchanced activity against gram-negative bacteria compared with natural penicillins and penicillinase-resistant penicillins.

…In vitro, aminopenicillins are generally active against gram-positive aerobic cocci and gram-position aerobic bacilli that are susceptible to natural penicillins. However, with the possible exception of enterococcal infections, natural penicillins are generally the penicillins of choice for the treatment of infections caused by gram-positive cocci that are susceptible to both natural penicillins and aminopenicillins. Like natural penicillins and extended-spectrum penicillins, aminopenicillins are readily hydrolyzed by staphylococcal penicillinases and are therefore inactive against penicillinase-producing strains of S. aureua and S. epidermidis.

…Aminopenicillins are generally active in vitro against gram-negative aerobic cocci, gram-negative aerobic bacilli, and anaerobic bacteria that are susceptible to natural penicillins. In addition, aminopenicillins are active in vitro against some Enterobacteriaceae including some strains of Escherichia coli, Proteus mirabilis, Salmonella, and Shigella. Aminopenicillins are generally inactive against other Enterobateriaceae, Bacteroides fragilis, and Pseudomonas.

…Because clavulanic acid and sulbactam caninhibit certain b-lactamases that generally inactive aminopenicillins, combinations of amoxicillin and clavulanate potassium and combinations of ampicillin sodium and sulbactam sodium are active in vitro against many b-lactamase-producing organisms that are resistant to the aminopenicillins alone.

From: http://www.pharm.su.ac.th/PharmCourse/betalactam/html/pen-amino.htm

(I hope the link works, it’s been acting up)