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Analogue of ampicillin, is a semisynthetic antibiotic with essentially the all patients who present agar (Biokar®) were prepared and sterilized according to the manufacturers’ instructions. Another drug and may not reflect the rates.

Single, well-defined peak (C max ) at the side effects pharmaceutical companies to conduct expensive studies aimed at finding the shortest duration of treatment for various conditions.

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Amoxicillin has proven to elicit fewer serious side effects

than

penicillin, especially in children.

However, any of the serious side effects requires prompt medical attention. Women who are pregnant can take penicillin or amoxicillin, under medical

supervision

. However, women who are breastfeeding should not use either medicine as it can pass through to the baby and cause serious side effects. As penicillins do not distinguish between "good" and "bad" bacteria, intestinal flora can be seriously affected during treatment and for weeks afterward.

This bacterial reduction is what leads to diarrhea, yeast infections, flu-like symptoms, and/or reduced water and nutrient absorption (decreased urination as the body tried to retain water). To offset these side effects, some doctors and pharmacists recommend taking a probiotic while on antibiotics. Penicillin and amoxicillin interfere with oral contraceptives ("the pill" birth control), rendering them less effective.

If using birth control pills and antibiotics, a woman can become pregnant, so other forms of birth control are needed.

Anyone taking methotrexate (Rheumatrex, Trexall) or probenecid (Benemid), should tell his or her doctor about these and other medications. Penicillin and amoxicillin can enhance or inhibit the effects of these and other medications, especially those related to gastrointestinal and kidney functions. Patients should also tell their doctors about any vitamins, supplements, and/or herbal remedies they are currently using to avoid serious or even fatal drug interactions. Amoxicillin is considerably cheaper than penicillin, but neither antibiotic is very expensive.

According to GoodRx.com, Penicillin V Potassium pills (40 tablets of 500 mg each) range in price from $10.00 to $37.20. Amoxil, a brand name for amoxicillin (30 tablets of 500 mg each) ranges from $4.00 to $12.79.

Ernest Duchesne, a French physician, first noticed the microbial-inhibiting

effect

of the Penicillium mold in 1897. Despite using the mold to cure typhoid in guinea pigs, Duchesne's paper on the experiment was ignored. Penicillin, as such, was identified and isolated by Scottish physician Alexander Fleming, in 1928, using Penicillium

rubens

. Fleming isolated the mold's substance and proved it was non-toxic in humans, but the development of penicillin as a medicine was completed by Howard Florey, Ernst Chain, and Norman Heatley, an Austrian-German-British collaboration for which Florey and Chain won the Nobel Prize.

Because penicillin was difficult to produce and badly needed during World War II, treatments were limited to severe cases of infection.

Efforts to make the best use of penicillin often included collecting the urine of treated patients to "recycle" the medicine, as about 80% of penicillin is excreted within 3-5 hours. This proved ineffective and efforts to increase the time penicillin remained in the body led to the discovery of pairing it with probenecid, which blocked the body's natural "flushing" of penicillin and allowed the medicine to work for a longer period of time.

Once biosynthesis of penicillin became common and large amounts of the medicine were readily available, probenecid was eliminated from most treatments, although it is still used for particularly aggressive bacterial infections and in cases where resistant bacterial strains, such as MRSA, are present, or for treating H. pylori , the bacteria that causes most stomach ulcers. In 1961, ampicillin became the first penicillin-based antibiotic developed in a laboratory that used the penam structure.

The semi-synthetic formulation quickly proved to be as effective as other penicillins against most bacterial infections, but with the added advantage of resulting in fewer side effects.

Within a year of its development, it was in widespread use and opened the door to new formulations of penicillins, including amoxicillin, which entered the market in 1972. HPLC determination of amoxicillin comparative bioavailability in healthy volunteers after a single dose administration. Luis Renato Pires de Abreu 1 , Rodrigo Agustin Mas Ortiz Department of Pharmacology, State University of Campinas-UNICAMP, Campinas, Sao Paulo, Brazil.

Integrated Unit of Pharmacology and Gastroenterology-Sao Francisco University Medical School, Braganca Paulista, Sao Paulo, Brazil. Received 10 July 2002, Revised 28 April 2003, Accepted 16 June 2003. PURPOSE : An accurate, precise and sensitive HPLC assay was developed for

the

determination of amoxicillin in human plasma samples, to compare the bioavailability of two amoxicillin

capsule

(500mg) formulations (Amoxicilina from Brazil, as a test formulation and Amoxil® from SmithKline Beecham Laboratories Ltda., Brazil, as a reference formulations) in 24 volunteers of both sexes.

METHODS : Amoxicillin concentrations were analyzed by combined reversed phase liquid chromatography and UV detection (?=229 nm). Amoxicillin and cefadroxil (internal standard) were extracted from the plasma by addition of cold methanol.

The separation was achieved using the Lichrosorb® 10 m m, C18 reversed phase column at room temperature.

The mobile phase consisted of a 95% phosphate buffer (0.01mol/L), pH=4.8 and 5% acetonitrile mixture.

The study was

conducted

using an open randomized 2-period crossover balanced design with a 1-week washout period between the doses. Plasma samples were obtained over an 8-hour period. The bioequivalence between the two formulations was assessed by calculating individual peak plasma concentrations (C max ) and area under the curve (AUC 0-8h ) ratios (test/reference). The statistical interval proposed was 80-125%, as established by the US Food and drug administration Agency.

RESULTS : The internal standard and amoxicillin eluted about 4.2 and 5.2 min, respectively at a flow rate of 1.3ml/min. The mean absolute recovery of AMO in plasma was 90.0% at 3 m g/ml, 98.6% at 25 m g/ml and 95.3 at 50 m g/ml.

The assay showed excellent relationships between peak height ratios and plasma concentrations (r 2 ? 0.999). The limit of quantification was 1g/ml, based on 200l of plasma.

The geometric mean of Amoxicilina/Amoxil® 500mg capsules individual percentage ratio was 101.4% for AUC0-8h, and 99.9% for Cmax. The 90% confidence intervals were 98.3-104.4% and 95.7-103.9%, respectively.

CONCLUSION : This simple, rapid and selective method is suitable for pharmacokinetic, bioavailability and bioequivalence studies.

Since the 90% CI for both C max and AUC 0-8h lies within the 80-125% interval proposed by the Food and Drug Administration, it was concluded that Amoxicilina 500mg capsules was bioequivalent to Amoxil® capsules 500mg, in terms of both the rate and extent of absorption.

Amoxicillin [[2S-[2 a ,5 a ,6?(S*)]]-6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxilic acid] is an oral semi-synthetic penicillin structurally related to ampicillin (Figure 1). The presence of a benzyl ring in the amoxicillin trihydrate capsules side chain extends the

antibacterial

activity to gram-negative bacteria (1-4).

The action mechanism of these antibiotics has not been unequivocally established,

but

it is thought they may interfere with peptidoglycan bacterial cell wall synthesis in the effected organisms (5-10). Figure 1: Structures of ampicillin, amoxicillin and cefadroxil cheap amoxicillin (internal standard).

Amoxicillin (AMO) shows high absorption after oral administration, and this is not altered by the concomitant ingestion with food (6-8). AMO reaches C max (8 m g/ml) about 2 hours after administration, exhibits low binding with plasma proteins (17%), is quickly distributed through the body, and has an elimination half-life of 1 hour (7-10).

The elimination of the drug occurs preferentially by excretion in the urine, with about 60% of an orally administered dose and 75% of a parenteral dose being excreted unchanged (11-13). AMO is commercially available in the form of capsules and tablets containing 250 and 500mg (as amoxicillin free base) for oral administration. It is amoxicillin prescription cost also available in the form of suspensions containing 125 and 250mg/5ml. AMO is presently the most commonly used antibiotic.To understand the pharmacokinetic behavior of AMO in humans, a reliable quantitative method is needed. Several high performance liquid chromatography (HPLC) methods for the determination of amoxicillin in body fluids have been developed. Most of the methods use direct UV detection at low wavelengths (?=225-330 nm) (14-19). Fluorimetric detection (20-22), ion-paired reagents and special techniques such as postcolumn derivatization or column switching (14, 20, 23) have been used to enhance sensitivity and selectivity.

Different methods of sample preparation have been applied prior to the chromatographic analysis, mostly based on protein precipitation (15, 19, 20), liquid-liquid extraction (21) or more complicated extractions such as solid-phase extraction (17, 18, 24-26). The objective of this study was to compare the pharmacokinetic profiles and to evaluate the bioequivalence of two AMO formulations, in 24 healthy volunteers of both sexes. The test AMO capsule (500mg) formulation from Brazil was compared with a commercial AMO capsule (500mg) formulation produced by SmithKline Beecham, which has

been

defined as the reference standard by the national regulatory agency (ANVISA). After evaluation of the various conditions of the HPLC assay, a suitable and simple assay for the measurement of amoxicillin in human plasma was developed using reversed-phase HPLC and direct UV detection. Acetonitrile (ACN) was purchased from EM Science (Gibbstown, NJ, USA); methanol (MeOH), sodium hydroxide (NaOH) and sodium phosphate salts (Na 2

HPO

4 /NaH 2 PO 4 ) were purchased from Merck (Rio de Janeiro, RJ, Brazil).

The HPLC grade solvents ACN and MeOH were used as received. Amoxicillin and cefadroxil (internal standard) were purchased from USP Pharmacopeia (New York, NY, USA).

The deionized water was prepared using Milli-Q system (Millipore, Molsheim, France).

Stock solution of AMO (1mg/ml) was prepared in H 2 O:ACN (95:5).

Working standard solutions were prepared from the stock solution by sequential dilution with H 2 O:ACN (95:5) to yield final concentrations of 1, 10 and 100 ?g/ml. Stock solution of cefadroxil (internal standard) was prepared in MeOH (1mg/ml).

Stock and amoxicillin & potassium clavulanate working standard solutions were protected from light and stored at -20°C until used. Calibration standards were obtained by adding known amounts of AMO to drug-free plasma to achieve the concentrations of 1, 5, 10, 20, 40 and 50 m g/ml.

Three quality controls of low (3?g/ml), middle (25 m g/ml) and high (50 m g/ml) concentrations were prepared by adding known amounts of AMO to drug-free plasma.

Plasma solutions were protected from light and stored at -70°C until used.

AMO and cefadroxil (internal standard) were extracted from human plasma samples by protein precipitation. A 200 m aliquot of each plasma sample was transferred to a 1.5 ml polypropylene tube.

Then, 15 m l of 1 mg/ml internal standard solution and 400 m l of cold MeOH (kept on ice) were added. After a brief vortex mixing, the tubes were centrifuged (14000 rpm at 4°C for 15 min).

A 100 m aliquot of the supernatant was transferred to the injection vials and 20 m l were injected into the chromatographic system.

Quality controls were performed in duplicate for each batch. All samples from a single volunteer were analyzed on the same day in order to avoid inter-assay variation.

The analyses were performed on a Shimadzu chromatographic system (Kyoto, Japan) equipped with a LC-10AD VP pump, an SIL-10A VP auto-sampler, an SPD-10A VP UV detector and an SCL 10 A-VP controller unit. The drug analysis data were acquired and processed using CLASS-VP (v.6.2) software running under Windows 98 on a Pentium PC. The mobile phase involved a mixture of phosphate buffer (0.01mol/L), pH=4.8 and ACN (95:5 v/v), pumped at a flow rate of 1.3ml/min through the column (Lichrosorb® 10 m m RP 18, 250 x 4.6mm with a guard column Securityguard® C18 10 m m, 4 x 3.0mm; Phenomenex, CA, USA) at room temperature.

Peaks were monitored by UV absorbance at 229nm, sensitivity of 0.005AUFS. Quantification of AMO was obtained by plotting AMO to internal standard

peak

height ratios as a function of concentration.

Drug-free plasma was spiked with known amounts of the drug to achieve the concentrations of 3, 25 and 50 m g/ml (n=3) and stored at -70°C.

Those samples were used to investigate the stability of AMO over a period of 1 month.

No internal standard was added prior to the analysis. The specificity of the method was determined by comparing the chromatograms obtained from the samples containing AMO and internal standard

with

those obtained from blank samples.

Limit of detection (LOD) and limit of quantification (LOQ) LOD is a parameter that provides the lowest concentration of analyte in a sample that can be detected, but not quantified, under the stated experimental conditions.

The LOD was determined by using the signal-to-noise ratio and comparing test results from samples with known concentrations of analyte against blank samples. The analyte concentration that produced a signal-to-noise ratio of 3:1 was accepted as the LOD.

The LOQ is defined as the lowest concentration of analyte that can be determined with acceptable precision and accuracy under the stated experimental conditions.

The LOQ was

estimated

by analyzing samples with known amounts of AMO, at progressively lower concentrations, starting at the lower end of the calibration curves.

The LOQ was considered as the concentration level in which accuracy and precision were still better than 20%.

The analytical recovery of AMO was determined at concentrations of 1, 3, 25 and 50 m g/ml (n=3).

Drug-free plasma was spiked with known amounts of the drug to achieve the concentration previously specified. These samples were processed by the analytical method described above and peak heights were compared with the peak heights obtained by direct injection of the drugs in the mobile phase.

The linearity study was carried out in the range of 1 to 50 m g/ml (n=4).

To access linearity, drug-free

plasma

was spiked with known amounts of the drug to achieve the concentrations of 1, 5, 10, 20, 40 and 50 m g/ml.

Precision was determined as the coefficient of variation (CV), and the accuracy as the percentage relative error (RE).



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