Amoxicillin

Other names included commercial trade names:

Chemical formula:  C₁₆H₁₉N₃O₅S

Systematic (IUPAC) name: (2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Amoxicillin (INN), formerly amoxycillin (BAN), is a moderate-spectrum, bacteriolytic, 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 β-lactam antibiotics.
Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, and so may be given with clavulanic acid to decrease its susceptibility.

Amoxicillin capsules: Each capsule of AMOXIL, with royal blue opaque cap and pink opaque body, contains 500 mg amoxicillin as the trihydrate. The cap and body of the 500-mg capsule are imprinted with AMOXIL and 500. Inactive ingredients: D&C Red No. 28, FD&C Blue No. 1, FD&C Red No. 40, gelatin, magnesium stearate, and titanium dioxide.

Amoxicillin tablets: Each tablet contains 500 mg or 875 mg amoxicillin as the trihydrate. Each film-coated, capsule-shaped, pink tablet is debossed with AMOXIL centered over 500 or 875, respectively. The 875-mg tablet is scored on the reverse side. Inactive ingredients: Colloidal silicon dioxide, crospovidone, FD&C Red No. 30 aluminum lake, hypromellose, magnesium stearate, microcrystalline cellulose, polyethylene glycol, sodium starch glycolate, and titanium dioxide.

Amoxicillin chewable tablets: Each cherry-banana-peppermint-flavored tablet contains 200 mg or 400 mg amoxicillin as the trihydrate. Each 200-mg chewable tablet contains 0.0005 mEq (0.0107 mg) of sodium; the 400-mg chewable tablet contains 0.0009 mEq (0.0215 mg) of sodium. The 200-mg and 400-mg pale pink round tablets are imprinted with the product name AMOXIL and 200 or 400 along the edge of 1 side. Inactive ingredients: Aspartame®, crospovidone NF, FD&C Red No. 40 aluminum lake, flavorings, magnesium stearate, and mannitol.

Powder for Oral Suspension: Each 5 mL of reconstituted suspension contains 200 mg, 250 mg, or 400 mg amoxicillin as the trihydrate. Each 5 mL of the 250-mg reconstituted suspension contains 0.15 mEq (3.36 mg) of sodium. Each 5 mL of the 200-mg reconstituted suspension contains 0.15 mEq (3.39 mg) of sodium; each 5 mL of the 400-mg reconstituted suspension contains 0.19 mEq (4.33 mg) of sodium.

Pediatric Drops for Oral Suspension: Each mL of reconstituted suspension contains 50 mg amoxicillin as the trihydrate and 0.03 mEq (0.69 mg) of sodium.

Amoxicillin trihydrate for oral suspension 200 mg/5 mL, 250 mg/5 mL (or 50 mg/mL), and 400 mg/5 mL are bubble-gum-flavored pink suspensions. Inactive ingredients: FD&C Red No. 3, flavorings, silica gel, sodium benzoate, sodium citrate, sucrose, and xanthan gum.

Amoxicillin mode of action

Main article: Beta-lactam antibiotic
Amoxicillin acts by inhibiting the synthesis of bacterial cell wall. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell walls of both Gram-positive and Gram-negative bacteria.

PRESCRIPTION: Yes.

GENERIC AVAILABLE: Yes.

Indications

AMOXIL is indicated in the treatment of infections due to susceptible (ONLY β-lactamase- negative) strains of the designated microorganisms in the conditions listed below

• Infections of the ear, nose, and throat - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae , Staphylococcus spp., or H. influenzae.
• Infections of the genitourinary tract - due to E. coli, P. mirabilis, or E. faecalis.
• Infections of the skin and skin structure - due to Streptococcus spp. (α- and β-hemolytic strains only), Staphylococcus spp., or E. coli.
• Infections of the lower respiratory tract - due to Streptococcus spp. (α- and β-hemolytic strains only), S. pneumoniae, Staphylococcus spp., or H. influenzae.
• Gonorrhea, acute uncomplicated (ano-genital and urethral infections) - due toN. gonorrhoeae (males and females). H. pylori eradication to reduce the risk of duodenal ulcer recurrence
• Triple Therapy: AMOXIL/clarithromycin/lansoprazole
  AMOXIL, in combination with clarithromycin plus lansoprazole as triple therapy, is indicated for the treatment of patients with H. pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) to eradicate H. pylori. Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See Clinical Studies and DOSAGE AND ADMINISTRATION.)
• Dual Therapy: AMOXIL/lansoprazole
  AMOXIL, in combination with lansoprazole delayed-release capsules as dual therapy, is indicated for the treatment of patients with H. pylori infection and duodenal ulcer disease (active or 1-year history of a duodenal ulcer) who are either allergic or intolerant to clarithromycin or in whom resistance to clarithromycin is known or suspected. (See the clarithromycin package insert, MICROBIOLOGY.) Eradication of H. pylori has been shown to reduce the risk of duodenal ulcer recurrence. (See Clinical Studies and DOSAGE AND ADMINISTRATION.)

To reduce the development of drug-resistant bacteria and maintain the effectiveness of AMOXIL and other antibacterial drugs, AMOXIL should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy.
Indicated surgical procedures should be performed.

Amoxicillin formulations

Amoxicillin in trihydrate form is available as capsules, chewable and dispersable tablets plus syrup and pediatric suspension for oral use, and as the sodium salt for intravenous administration. It is one of the most common antibiotics prescribed for children, and the liquid forms are helpful where the patient might find it difficult to take tablets or capsules. It has three ionizable groups. A once daily dosing form (Moxatag) was approved by the American FDA in January 2008.

HOW SUPPLIED

Capsules of AMOXIL: Each capsule contains 500 mg amoxicillin as the trihydrate.

500-mg Capsule

• NDC 0029-6007-32 Bottles of 500

Tablets of AMOXIL: Each tablet contains 500 mg or 875 mg amoxicillin as the trihydrate.

500-mg Tablet

• NDC 0029-6046-20 Bottles of 100

875-mg Tablet

• NDC 0029-6047-20 Bottles of 100

Chewable Tablets of AMOXIL:

Each cherry-banana-peppermint-flavored tablet contains 200 mg or 400 mg amoxicillin as the trihydrate.

200-mg Tablet

• NDC 0029-6044-12 Bottles of 20

400-mg Tablet

• NDC 0029-6045-12 Bottles of 20

AMOXIL for Oral Suspension:

Each 5 mL of reconstituted bubble-gum-flavored suspension contains 200, 250, or 400 mg amoxicillin as the trihydrate.

200 mg/5 mL

• NDC 0029-6048-54 50-mL bottle
• NDC 0029-6048-55 75-mL bottle
• NDC 0029-6048-59 100-mL bottle
• NDC 0029-6048-18 5-mL unit dose bottle

250 mg/5 mL

• NDC 0029-6009-23 100-mL bottle
• NDC 0029-6009-22 150-mL bottle

400 mg/5 mL

• NDC 0029-6049-54 50-mL bottle
• NDC 0029-6049-55 75-mL bottle
• NDC 0029-6049-59 100-mL bottle
• NDC 0029-6049-18 5-mL unit dose bottle

Pediatric Drops of AMOXIL for Oral Suspension:

Each mL of bubble-gum-flavored reconstituted suspension contains 50 mg amoxicillin as the trihydrate.

• NDC 0029-6038-39 30-mL bottle

Store at or below 20°C

• 500-mg capsules
• 250-mg unreconstituted powder

Store at or below 25°C

• 200-mg and 400-mg unreconstituted powder
• 200-mg and 400-mg chewable tablets
• 500-mg and 875-mg tablets Dispense in a tight container.

Store Amoxil capsules as well as 125 and 250 mg dry powder at or below 20°C (68°F); tablets, chewable tablets, as well as 200 and 400 mg dry powder should be stored at or below 25°C(77°F). Store Trimox capsules and unreconstituted powder at or below 20°C (68°F) and chewable tablets at room temperature 15°-30°C (59°-86°F). Powder that has been mixed with water should be discarded after 14 days. Refrigeration is preferred but not required for powder mixed with water.Keep this medication in the container it came in, tightly closed, and out of reach of children. Store the capsules and tablets at room temperature and away from excess heat and moisture (not in the bathroom). Throw away any medication that is outdated or no longer needed. The liquid medication preferably should be kept in the refrigerator, but it may be stored at room temperature. Throw away any unused medication after 14 days. Do not freeze. Talk to your pharmacist about the proper disposal of your medication.

AMOXIL and AUGMENTIN are registered trademarks of GlaxoSmithKline., CLINITEST is a registered trademark of Miles, Inc., CLINISTIX is a registered trademark of Bayer Corporation., CLOtest is a registered trademark of Kimberly-Clark Corporation. GlaxoSmithKline, Research Triangle Park, NC 27709. October 2006. FDA revision date: 6/9/2008

Amoxicillin side effects

Side effects are as those for other beta-lactam antibiotics. Side effects include nausea, vomiting, irritability, volatile mood swings, disorientation, aggressiveness and easy fatigue. Loose bowel movements (diarrhea) also may occur.

The onset of an allergic reaction to amoxicillin can be very sudden and intense - emergency medical attention must be sought as quickly as possible. The initial onset of such a reaction often starts with a change in mental state; skin rash with intense itching (often beginning in fingertips and around groin area and rapidly spreading) and sensations of fever, nausea and vomiting. Any other symptoms that seem even remotely suspicious must be taken very seriously.

As with other penicillins, it may be expected that untoward reactions will be essentially limited to sensitivity phenomena. They are more likely to occur in individuals who have previously demonstrated hypersensitivity to penicillins and in those with a history of allergy, asthma, hay fever, or urticaria. The following adverse reactions have been reported as associated with the use of penicillins:

Infections and Infestations: Mucocutaneous candidiasis.

Gastrointestinal:

Nausea, vomiting, diarrhea, black hairy tongue, and hemorrhagic/pseudomembranous colitis.

Onset of pseudomembranous colitis symptoms may occur during or after antibiotic treatment.

Hypersensitivity Reactions:

Anaphylaxis

Serum sickness-like reactions, erythematous maculopapular rashes, erythema multiforme, Stevens-Johnson syndrome, exfoliative dermatitis, toxic epidermal necrolysis, acute generalized exanthematous pustulosis, hypersensitivity vasculitis and urticaria have been reported.

NOTE: These hypersensitivity reactions may be controlled with antihistamines and, if necessary, systemic corticosteroids. Whenever such reactions occur, amoxicillin should be discontinued unless, in the opinion of the physician, the condition being treated is life-threatening and amenable only to amoxicillin therapy.

Liver:

A moderate rise in AST (SGOT) and/or ALT (SGPT) has been noted, but the significance of this finding is unknown. Hepatic dysfunction including cholestatic jaundice, hepatic cholestasis and acute cytolytic hepatitis have been reported.

Renal:

Crystalluria has also been reported (see OVERDOSAGE).

Hemic and Lymphatic Systems:

Anemia, including hemolytic anemia, thrombocytopenia, thrombocytopenic purpura, eosinophilia, leukopenia, and agranulocytosis have been reported during therapy with penicillins. These reactions are usually reversible on discontinuation of therapy and are believed to be hypersensitivity phenomena.

Central Nervous System:

Reversible hyperactivity, agitation, anxiety, insomnia, confusion, convulsions, behavioral changes, and/or dizziness have been reported rarely.

Miscellaneous:

Tooth discoloration (brown, yellow, or gray staining) has been rarely reported. Most reports occurred in pediatric patients. Discoloration was reduced or eliminated with brushing or dental cleaning in most cases.

Combination Therapy with Clarithromycin and Lansoprazole:

In clinical trials using combination therapy with amoxicillin plus clarithromycin and lansoprazole, and amoxicillin plus lansoprazole, no adverse reactions peculiar to these drug combinations were observed. Adverse reactions that have occurred have been limited to those that had been previously reported with amoxicillin, clarithromycin, or lansoprazole.

Triple Therapy:

Amoxicillin/Clarithromycin/Lansoprazole: The most frequently reported adverse events for patients who received triple therapy were diarrhea (7%), headache (6%), and taste perversion (5%). No treatment-emergent adverse events were observed at significantly higher rates with triple therapy than with any dual therapy regimen.

Dual Therapy:

Amoxicillin/Lansoprazole: The most frequently reported adverse events for patients who received amoxicillin three times daily plus lansoprazole three times daily dual therapy were diarrhea (8%) and headache (7%). No treatment-emergent adverse events were observed at significantly higher rates with amoxicillin three times daily plus lansoprazole three times daily dual therapy than with lansoprazole alone.

Non-allergic amoxicillin rash

Somewhere between 3% to 10% of children taking amoxicillin (or ampicillin) show a late-developing (>72 hours after beginning medication and having never taken penicillin-like medication previously) possibly itchy rash, which is sometimes referred to as the "amoxicillin rash." The rash can also occur in adults.

The rash is described as maculopapular or morbilliform (measles-like; therefore, in medical literature, "amoxicillin-induced morbilliform rash"). It starts on the trunk and can spread from there. This rash is unlikely to be a true allergic reaction, and is not a contra-indication for future amoxicillin usage, nor should current regimen necessarily be stopped. However, as mentioned above, this common amoxicillin rash and a dangerous allergic reaction cannot easily be distinguished by inexperienced persons, and therefore a health professional should be consulted if a rash develops. (Pichichero, 2005; Schmitt 2005)

A non-allergic amoxicillin rash may also be an indicator of infectious mononucleosis: Some studies indicate that approximately 80-90% of patients with acute Epstein Barr virus infection treated with amoxicillin or ampicillin develop such a rash.

DRUG INTERACTIONS

Probenecid decreases the renal tubular secretion of amoxicillin. Concurrent use of amoxicillin and probenecid may result in increased and prolonged blood levels of amoxicillin.

Chloramphenicol, macrolides, sulfonamides, and tetracyclines may interfere with the bactericidal effects of penicillin. This has been demonstrated in vitro; however, the clinical significance of this interaction is not well documented.

In common with other antibiotics, AMOXIL may affect the gut flora, leading to lower estrogen reabsorption and reduced efficacy of combined oral estrogen/progesterone contraceptives.

Drug/Laboratory Test Interactions: High urine concentrations of ampicillin may result in falsepositive reactions when testing for the presence of glucose in urine using CLINITEST®, Benedict's Solution, or Fehling's Solution. Since this effect may also occur with amoxicillin, it is recommended that glucose tests based on enzymatic glucose oxidase reactions (such as CLINISTIX®) be used.

Following administration of ampicillin to pregnant women, a transient decrease in plasma concentration of total conjugated estriol, estriol-glucuronide, conjugated estrone, and estradiol has been noted. This effect may also occur with amoxicillin.

WARNINGS

(ANAPHYLACTIC) REACTIONS HAVE BEEN REPORTED IN PATIENTS ON PENICILLIN THERAPY. ALTHOUGH ANAPHYLAXIS IS MORE FREQUENT FOLLOWING PARENTERAL THERAPY, IT HAS OCCURRED IN PATIENTS ON ORAL PENICILLINS. THESE REACTIONS ARE MORE LIKELY TO OCCUR IN INDIVIDUALS WITH A HISTORY OF PENICILLIN HYPERSENSITIVITY AND/OR A HISTORY OF SENSITIVITY TO MULTIPLE ALLERGENS. THERE HAVE BEEN REPORTS OF INDIVIDUALS WITH A HISTORY OF PENICILLIN HYPERSENSITIVITY WHO HAVE EXPERIENCED SEVERE REACTIONS WHEN TREATED WITH CEPHALOSPORINS. BEFORE INITIATING THERAPY WITH AMOXIL, CAREFUL INQUIRY SHOULD BE MADE CONCERNING PREVIOUS HYPERSENSITIVITY REACTIONS TO PENICILLINS, CEPHALOSPORINS, OR OTHER ALLERGENS. IF AN ALLERGIC REACTION OCCURS, AMOXIL SHOULD BE DISCONTINUED AND APPROPRIATE THERAPY INSTITUTED. SERIOUS ANAPHYLACTIC REACTIONS REQUIRE IMMEDIATE EMERGENCY TREATMENT WITH EPINEPHRINE. OXYGEN, INTRAVENOUS STEROIDS, AND AIRWAY MANAGEMENT, INCLUDING INTUBATION, SHOULD ALSO BE ADMINISTERED AS INDICATED.

Pseudomembranous colitis has been reported with nearly all antibacterial agents, including amoxicillin, and may range in severity from mild to life-threatening. Therefore, it is important to consider this diagnosis in patients who present with diarrhea subsequent to the administration of antibacterial agents.

Treatment with antibacterial agents alters the normal flora of the colon and may permit overgrowth of clostridia. Studies indicate that a toxin produced by Clostridium difficile is a primary cause of “antibiotic-associated colitis.”

After the diagnosis of pseudomembranous colitis has been established, appropriate therapeutic measures should be initiated. Mild cases of pseudomembranous colitis usually respond to drug discontinuation alone. In moderate-to-severe cases, consideration should be given to management with fluids and electrolytes, protein supplementation, and treatment with an antibacterial drug clinically effective against C. difficile colitis.

Proprietary preparations

Amoxicillin is one of the semi-synthetic penicillins discovered by Beecham scientists. The patent for amoxicillin has expired, thus amoxicillin is marketed under many trade names.

Consumer

IMPORTANT NOTE:

This is a summary and does not contain all possible information about this product. For complete information about this product or your specific health needs, ask your health care professional. Always seek the advice of your health care professional if you have any questions about this product or your medical condition. This information is not intended as individual medical advice and does not substitute for the knowledge and judgment of your health care professional. This information does not contain any assurances that this product is safe, effective, or appropriate for you.

AMOXICILLIN - ORAL

(a-MOX-i-SIL-in)

COMMON BRAND NAME(S): Amoxil

USES:

Amoxicillin is a penicillin-type antibiotic used to treat a wide variety of bacterial infections. It works by stopping the growth of bacteria.

This antibiotic treats only bacterial infections. It will not work for viral infections (e.g., common cold, flu). Unnecessary use or overuse of any antibiotic can lead to its decreased effectiveness.

HOW TO USE:

Take this medication by mouth with or without food, usually every 8 or 12 hours, or as directed by your doctor. The dosage is based on your medical condition and response to therapy.

Drink plenty of fluids while using this medication unless your doctor tells you otherwise.

Antibiotics work best when the amount of medicine in your body is kept at a constant level. Therefore, take this drug at evenly spaced intervals.

Continue to take this medication until the full-prescribed amount is finished even if symptoms disappear after a few days. Stopping the medication too early may allow bacteria to continue to grow, which may result in a relapse of the infection.

Inform your doctor if your condition persists or worsens.

Before taking amoxicillin

tell your doctor and pharmacist if you are allergic to amoxicillin, penicillin, cephalosporins, or any other medications.

tell your doctor and pharmacist what prescription and nonprescription medications, vitamins, nutritional supplements, and herbal products you are taking. Be sure to mention any of the following: chloramphenicol (Chlormycetin), other antibiotics, and probenecid (Benemid). Your doctor may need to change the doses of your medications or monitor you carefully for side effects.

tell your doctor if you have or have ever had kidney disease, allergies, asthma, hay fever, hives, or phenylketonuria.

tell your doctor if you are pregnant, plan to become pregnant, or are breast-feeding. If you become pregnant while taking amoxicillin, call your doctor.

information are getted from

• http://en.wikipedia.org/wiki/Amoxicillin
• http://www.rxlist.com/amoxicillin-drug.htm