Article: Amoxicillin

Amoxicillin
Systematic (IUPAC) name
7-[2-amino-2-(4-hydroxyphenyl) -acetyl]amino-3,3-dimethyl-6-oxo -2-thia-5-azabicyclo[3.2.0]heptane -4-carboxylic acid
Identifiers
CAS number	26787-78-0
ATC code	J01CA04
PubChem	9045
DrugBank	APRD00248
Chemical data
Formula	C16H19N3O5S
Mol. weight	365.4 g/mol
Pharmacokinetic data
Bioavailability	95% oral
Metabolism	less than 30% Hepatic biotransformed
Half life	61.3 minutes
Excretion	renal
Therapeutic considerations
Pregnancy cat.	A(AU)
Legal status	POM(UK)
Routes	oral, intravenous

Amoxicillin (INN) or amoxycillin (former BAN) is a moderate-spectrum β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, and so may be given with clavulanic acid to decrease its susceptability (see below). It is currently marketed by GlaxoSmithKline under the trade name Amoxil.

Mode of action

Amoxicillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria.

Main article: beta-lactam antibiotic

Microbiology

Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative organisms. Some examples of susceptible and resistant organisms, from the Amoxil® Approved Product Information (GSK, 2003), are listed below.

Susceptible Gram-positive organisms

Streptococcus spp., Diplococcus pneumoniae, non β-lactamase-producing Staphylococcus spp., and Streptococcus faecalis.

Susceptible Gram-negative organisms

Haemophilus influenzae, Neisseria gonorrhoeae, Neisseria meningitidis, Escherichia coli, Proteus mirabilis and Salmonella spp.

Resistant organisms

Penicillinase-producing organisms, particularly penicillinase-producing Staphylococcus spp. Penicillinase-producing N. gonorrhoeae and H. influenzae are also resistant.

All strains of Pseudomonas spp., Klebsiella spp., Enterobacter spp., indole-positive Proteus spp., Serratia marcescens, and Citrobacter spp. are resistant.

The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing.

Doubling the routinely given concentration (in pediatrics) of amoxicillin has been shown to eradicate intermediately resistant organisms (Red Book, 2003 Report of the Committee on Infectious Diseases, American Academy of Pediatrics).

Formulations

Amoxicillin in trihydrate form is available as capsules, tablets, or syrup for oral use, and as the sodium salt for intravenous administration.

Amoxicillin and Clavulanic acid

Amoxicillin (in either trihydrate or sodium salt forms) may be combined with Clavulanic acid (as potassium clavulanate), a β-lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through β-lactamase production. This formulation is referred to as Co-amoxiclav (British Approved Name), but commonly by proprietary names such as Augmentin and Clamoxyl.

Main article: Co-amoxiclav

Proprietary Preparations

The patent for amoxicillin has expired. Thus amoxicillin is marketed under many trade names including: Actimoxi®, Amoxibiotic®, Amoxicilina®, Apo-Amoxi®, Cilamox®, Dispermox®, Isimoxin®, Lamoxy®, Ospamox®, Pamoxicillin®, Polymox®, Trimox®, Tolodina®, Wymox®, Zerrsox® and Zimox®.